Claire's Picks Archives - Claire Wears Tue, 24 Mar 2026 19:02:36 +0000 en-US hourly 1 https://wordpress.org/?v=6.9.4 http://clairewears.com/wp-content/uploads/2026/03/cropped-cropped-image-17-32x32.jpg Claire's Picks Archives - Claire Wears 32 32 The ‘Unsexy’ Trend That’s Actually Super Attractive According to Dating Experts http://clairewears.com/the-unsexy-trend-thats-actually-super-attractive-according-to-dating-experts/ http://clairewears.com/the-unsexy-trend-thats-actually-super-attractive-according-to-dating-experts/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/the-unsexy-trend-thats-actually-super-attractive-according-to-dating-experts/ Last month, I got dumped. via text. on my birthday. while i was in the middle of buying ingredients to cook this person dinner. As one does in these situations,…

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Last month, I got dumped. via text. on my birthday. while i was in the middle of buying ingredients to cook this person dinner.

As one does in these situations, I immediately called my friend Emma for emergency emotional triage. After listening to me ugly cry for approximately 17 minutes, she said something that temporarily stopped my crying through pure confusion: “what were you wearing when you met him?”

This seemed like an odd question, considering the circumstances. “uh, i was wearing jeans and that oversized beige cardigan i bought at the vintage store? the big, chunky one that looks like it belongs to someone’s grandfather? why?”

there was a long pause before emma said, “oh yeah. that’s probably why he asked you out in the first place. trust me.”

i was confused. the cardigan in question is big, shapeless and the colour of oatmeal. it has large pockets capable of holding an entire convenience store’s worth of snacks. it is clearly unattractive.

if the sweater were a person, it would be a middle school math teacher named gerald who collects commemorative spoons and goes to bed at 8:30 pm.

“emma, what are you talking about? that cardigan is basically a form of birth control,” i replied.

no, no, it’s a thing,” she said. “big, oversized cardigans are actually very sexy right now. i read an article where dating coaches were saying it’s like the new sexy. something about being cozy and approachable.”

i was skeptical, at the least. however, emma’s comment stuck with me because it was easier to think about sweaters than to process my birthday dumping. and since i am a fashion writer who is pathologically unable to leave any style-related claim unexplored, i decided to explore this further.

is the unattractive sweater truly the new sexy? and more generally, are there other “unattractive” fashion choices that are indeed attractive to potential partners? is everything i know about how to dress for a first date totally wrong?

to begin exploring this, i contacted a few dating coaches/relationship experts and expected to receive the typical suggestions regarding how to emphasize the silhouette of one’s body through clothing, as well as strategically expose skin. instead, i received an ear full about the unexpectedly alluring quality of deliberately unattractive wardrobe choices.

“the oversized cardigan is actually a perfect example of what we refer to as ‘approachable attractiveness’,” explains dr. maya rodriguez, a relationship psychologist who consults with a few dating apps on user behavior. “it signals that you are comfortable with yourself, and that you don’t put forth an obvious amount of effort, which paradoxically translates to confidence—and that is one of the most attractive qualities universally.”

apparently, my dumpage had absolutely nothing to do with my cardigan. if anything, the sweater was likely the reason he asked me out in the first place. the betrayal runs deep!

but dr. rodriguez was not the only expert raving about deliberately unsexifying style. dating coach terrence jackson, who works with clients in nyc and los angeles, has been suggesting to his clients to include what he refers to as “comfort signaling” in their first date wardrobe.

“i’ve been telling my clients to steer clear of the obvious ‘try to be sexy’ options for years,” jackson explained. “particularly for women dating men, there is something about an oversized sweater, a pair of worn-in jeans, even those clunky “ugly” shoes—that provide an immediate sense of authenticity and approachability. my clients who choose this option consistently report stronger connections with their dates.”

the numbers support this as well. dating app hinge recently analyzed photos in the top 1000 most successful profiles (by measure of matches and conversations that resulted in sharing phone numbers) and found that casual, slightly sloppy looks greatly outperform conventionally appealing first-date attire.

“profiles featuring oversized knitwear had 30 percent more positive interactions than those featuring more typically ‘sexy’ clothing,” reports jin park, a trend analyst at the company. “we’ve also seen a 45 percent increase in positive reactions to photos featuring chunky loafers, flat shoes, minimal makeup, and other perceived “unsexy” style options.”

this trend is not exclusive to heteronormative dating. “across all gender identities and sexual orientations, we are seeing a shift towards the value of authenticity over the typical ‘sexy’ ideal,” park continued. “the time of dressing like you are trying to be as attractive as possible is basically over.”

to gain a more personal perspective, i solicited feedback from my instagram followers. i asked them to share examples of the “unsexy” things they find attractive in a partner’s style. the responses poured in so quickly that my phone almost crashed.

“men with those massive wire-framed glasses that look like they were issued by the soviet government in 1983,” responded one woman. “something about a man who does not care whether his glasses are ‘cool’ is super attractive to me.”

“somewhat too short pants on women,” responded a man. “not intentionally cropped, but like they’ve had them for years, and they shrunk a bit in the washer. it’s cute.”

“work boots that are actually scratched from work,” commented another. “not the polished construction boots people wear to brunch, but the ones that demonstrate someone actually constructs things.”

and yes, many, many people specifically mentioned oversized, shapeless cardigans as attractive. emma, it appears, was correct.

what is happening here? have we simply decided that “sexy” is not sexy anymore? and if so, what does that mean for how we dress when we attempt to attract a partner?

according to dr. rodriguez, this change represents larger cultural shifts in how we view attraction and relationships. “after years of highly filtered, perfectly curated social media displays of oneself, there is a growing disdain for obvious effort,” she explains. “showing up in something deliberately unsexy demonstrates that you are not attempting to seduce anyone with your clothing—you are inviting them to meet the real you.”

this mirrors something i’ve observed in the world of fashion as well. the most stylish people will often wear items that defy common assumptions about what constitutes “flattering” or “sexy”. the coolest person at any fashion event is rarely the individual wearing a fitted dress and high-heeled shoes—it is usually someone wearing a visually interesting combination of items that emphasizes comfort and personality rather than the traditional definition of sex appeal.

however, i wished to test this theory beyond expert opinion and anecdotal evidence. therefore, i devised a highly unscientific experiment. i would attend a series of first dates in deliberately unattractive outfits and observe the results. for comparison purposes, i utilized the same dating app, wore the same minimal makeup, and selected similar casual coffee shops. the only difference was the level of conventional sexiness in my outfit.

date #1: the control
for my control, i wore what would be traditionally regarded as a “cute” first date outfit: a fitted wrap dress that accentuates the waist, low heels, dainty jewelry, and hair that is down and styled. the type of outfit that women’s magazines have been recommending for first dates since about the dawn of time.

the date itself was okay—we had some decent conversation—but by the end of it, i wasn’t really interested, nor was he. we danced the awkward “we should do this again sometime” dance with no concrete plans. there was no second date.

date #2: the unsexy cardigan
for the second date, i wore the Cardigan—the exact same oatmeal-colored monstrosity that spawned this research—together with basic jeans, a plain white t-shirt, and flat ankle boots. my hair was tied back in a low ponytail. i wore the same light amount of makeup as date #1.

this date went surprisingly well. the conversation flowed naturally, and my date even brought up my sweater, stating it looked “really cozy” (which, let me tell you, was no way intended as a backhanded compliment). we spoke for nearly three hours. he requested a second date prior to us leaving the coffee shop, and there was a genuine sense of familiarity to our parting that was absent in date #1.

date #3: deliberately unflattering
for my third experiment, i took the idea of unsexy to its extreme: oversized vintage men’s pants secured by a canvas belt, clunky-looking orthopedic-style loafers, and a boxy button-down shirt. none of this outfit “flattered” my body in the conventional manner. i looked as though i was auditioning for a local theatre production of “annie hall: the later years.”

once again, the result was a successful connection. my date seemed to be genuinely interested in becoming better acquainted with me, asked thoughtful questions, and did not engage in the awful practice of men’s eyes drifting downward throughout the course of the conversation. we discussed books, shared family stories, and once again, planned a second meeting.

date #4: peak unsexy
for my last date, i channelled what i believe to be “peak comfort signaling”: baggy jeans, a cardigan even larger than the one from date #2 (one borrowed from my brother), scuffed shoes, messy bun, and minimalist jewelry. i looked like i might be ready to paint a wall or assist in moving furniture.

this turned out to be the best date of the series. not only did we have a strong connection, but there was also an obvious absence of the standard first-date performance anxiety on both parts. we walked around the neighborhood post-coffee, obtained tacos from a food truck, and sat in a park discussing topics until nightfall. the connection felt natural and effortless from the onset.

so, what did i take away from this experiment? while i cannot state unequivocally that deliberately unattractive clothing is the key to successful dating (n = 4), it appeared to be true.

“that makes sense when you think about it,” states dating coach jackson. “when you are not concerned with presenting a ‘sexy’ image—you are constantly checking if you are exposing too much or too little, adjusting straps or hems, etc.—you are present for the date. that presence is infinitely more attractive than any outfit could possibly be.”

dr. rodriguez provides additional insight: “conventionally ‘sexy’ clothing often serves as a barrier to forming genuine connections because it is inherently performative. when you are dressed in something that is comfortable and authentic to your everyday self, you are effectively stating ‘this is who i really am; not who i am pretending to be for your sake.’ that authenticity is attractive.”

there is also a certain degree of confidence involved in presenting oneself in deliberately unattractive attire. “wearing an item that society deems to be non-traditionally attractive requires a degree of confidence that is much sexier than adhering to societal standards,” states park. “it communicates that you are dressing for yourself, not for the approval of others.”

as previously stated, i have observed this principle within the realm of fashion for many years. the most respected style icons (e.g. phoebe philo, jenna lyons, raf simons)—all of whom have expressed a deliberate preference for deliberately unattractive elements: oversized proportions, practical footwear, comfort over conventional flattery—also express a style that is deemed fashionable in fashion circles and authentic in dating circles.

however, it is necessary to note that the attractiveness of deliberately unattractive clothing is not about hiding yourself or adopting slovenliness. it is about wearing things that emphasize comfort and authenticity over conventional sex appeal. the cardigan needs to be a cardigan that you love and feels good to wear—not just any large cardigan.

so, where does this leave traditional first-date dressing advice? is the little black dress dead? should we all begin attending romantic dinners in orthopedic shoes and loose-fitting garments?

for me, this exploration has been surprisingly freeing. as a fashion writer, i have spent many years contemplating how to fashionably display my body in a flattering manner, only to realise that pursuing flattery may not be the most effective means of connecting with others—not just in terms of style, but in terms of genuine connection.

currently, my go-to first date outfit consists of jeans, shoes i can actually walk in, and yes, frequently the enormous oatmeal cardigan. i have had more second dates in the last month than in the previous six months.

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The ‘Weird’ Thrift Store Section Actually Hiding the Coolest Fashion Finds http://clairewears.com/the-weird-thrift-store-section-actually-hiding-the-coolest-fashion-finds/ http://clairewears.com/the-weird-thrift-store-section-actually-hiding-the-coolest-fashion-finds/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/the-weird-thrift-store-section-actually-hiding-the-coolest-fashion-finds/ It’s the week before Thanksgiving, and I’m sitting at a diner in Park Slope with a cup of black coffee and nothing to do. The weather is unseasonable and I…

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It’s the week before Thanksgiving, and I’m sitting at a diner in Park Slope with a cup of black coffee and nothing to do. The weather is unseasonable and I feel agitated. Since leaving my job in January, I’ve spent a lot of time trying to fill the void. Most of my attempts to find meaningful things to do have ended in boredom. One of the reasons I think this happens is because I always try to make plans that go too far ahead of time. As a result, I usually rush to get as much done as I can in the little time I have. This afternoon is no different.

After checking the time again, I decided to visit a local thrift store I’d never actually looked into. I’ve passed it several times since moving to the area, but I’d never ventured inside. Part of that is probably because of the sign hanging above the entrance. The sign says “Linens & Textiles” in faded letters. I connect the words with dusty, worn curtains and stained bedding and almost never give them a second thought.

However, today I do enter the store. Once I enter the store, I’m immediately hit with the smells of old clothes, dust, and mildew. The air is heavy and thick, and I need to move through layers of old coats and broken umbrellas to reach the first rack of clothes. When I look through the first rack of clothes, I see mostly the same things I would have expected to see. Old jeans, faded t-shirts from the early 2000s, etc.

I continue walking down the aisle, until I reach the back of the store. I see a small section labeled “linens & textiles” and I pull out the contents. There are piles of stained bedding, torn tablecloths, and several shelves of what appear to be inexpensive looking curtains.

As I rummage through the bin, I see a blue object peeking out from under a stack of faded flower-printed bedding. I dig through the pile and find a hand dyed textile with the most beautiful shibori pattern. I hold it up to the light and take a closer look. I couldn’t believe what I was seeing.

This textile is obviously of high quality and handmade. If it were in a vintage boutique today, I wouldn’t be surprised if it was selling for hundreds of dollars. But here, in this thrift store, it seems to have been stuck. I kept digging and found a vintage batik from Southeast Asia, a hand-blocked Indian cotton with gold trim, and a hand embroidered piece with what appeared to be real silk.

In that moment, I realised— I had been thrifting incorrectly my whole adult life. The best treasures can be found in the least obvious places in the thrift store. Sections of the store that most people overlook.

Since then, I have become obsessed. I have been to 27 thrift stores in New York City, meticulously going through each store to find their textile sections. I have been stunned by what I have found, and the lessons I have learned about why these sections are so neglected.

So, let’s talk about the treasures I’ve found in these sections. I’ve found vintage silk scarves from famous designers that can be easily used as a traditional scarf or headband. I’ve also found scarves that can be wrapped around your purse or used as a decorative element. Additionally, I’ve found many scarves that can also be framed as art.

Tablecloths (especially round ones) are great to use as wrap skirts or capes. To create a skirt, simply wrap the tablecloth around your waist and tie with a belt. To create a cape, simply cut the tablecloth once. Curtain panels, especially those made of natural fibres, can also be easily turned into simple tunic dresses or tops.

Also, vintage sheets with interesting patterns tend to have much higher thread counts and softer cotton than modern sheets. Vintage sheets with unique designs can be easily repurposed into simple summer dresses, tops, or coordinating outfits.

Even shoppers who struggle with crafting can repurpose vintage textiles as oversized scarves or wraps without altering them. I have taken a number of vintage tablecloths and turned them into shawls by simply draping them over my shoulders. In doing so, I have brought attention to the intricate crochet or embroidery details on the edges of the cloth.

“People do not see textiles as potential fashion options. They are looking for pre-made garments to wear. However, if you train yourself to visualize the potential instead of the completed garment, everything changes,” said Mei-Lin, the owner of Threadbare Studios in Brooklyn.

One of the first steps to identifying a high-quality material is to identify the quality of the material. Tablecloths with rolled hems and hand-needlework detail are likely to be made of high-quality material. Faded curtains made of natural fibres (like linen or cotton) can potentially be turned into shirts, tunics, etc.

Use your hands, not just your eyes, suggests textile artist Juana Rodriguez. Run your hands gently over the fabric. Is it cold to the touch? That could mean it is silk. Has it a certain weight and drape? That could mean it is high-quality wool or linen. Your sense of touch will tell you much more about the quality of the fabric than your visual assessment.

My biggest success story has been buying an Hermès scarf. It was bought in the 1960s. When I bought it, it had a small stain in the top-right corner and it was faded. It cost me $2.00. After washing it gently with a silk-specific detergent, the stain disappeared. Today, an Hermès scarf from the 1960s sells for $500+ in vintage shops.

Many of the items I have found in the textile sections of thrift stores can be used as-is. Scarves are a great place to start. Look for silk, wool, or fine-cotton squares hidden amongst the polyester. I have found many Vera Neumann scarves (Vera Neumann is identified by her name printed in the corner of the scarf) and many other designer pieces. These can be worn as traditional scarves or headbands. They can be draped over the handle of your purse or used as decorative elements. Many can also be framed as art.

Round tablecloths can be turned into wrap skirts or capes. Simply wrap the cloth around your waist and tie with a belt. Square tablecloths can quickly be turned into ponchos with a single cut. Curtain panels (particularly those made of natural fibres) can easily be turned into simple tunic-style dresses or tops.

Vintage sheets in unique patterns have higher thread counts and softer cotton than contemporary sheets. Sheets in unique designs can easily be repurposed into simple summer dresses, tops, or coordinating outfits.

Even the most craft-challenged shopper can repurpose vintage textiles as oversized scarves or wraps with zero modifications. I have taken many vintage tablecloths and used them as shawls by simply draping them over my shoulder. In doing so, I have highlighted the intricacy of the crochet or embroidered details on the edges of the cloth.

“All of this comes down to seeing the possibilities rather than what the item looks like today,” states Anita Chen, a vintage dealer specializing in repurposing textiles. “Most people are extremely literal. They see a tablecloth and cannot imagine anything beyond putting it on a table. Fabric is fabric. The only limits are the limits of your imagination.”

Another major advantage of finding textiles in thrift stores is the pricing. While the prices for second-hand clothing have dramatically risen in recent years (due in part to the rise of second-hand shopping and resale culture), the textile sections remain relatively inexpensive.

No one is competing for these items, explains Sam Rivera, a former manager at a thrift store. We price these items as low as possible to encourage sales because they consume a lot of our storage space and we don’t sell them nearly as fast as we do clothing. For instance, a beautiful tablecloth could sit on the shelf for months unless we practically give it away.

This pricing discrepancy is an excellent opportunity for fashion-minded shoppers. I have amassed enough quality textiles to adopt a one-in/one-out policy for my textile collection. Recently, I purchased a 1970s Indian cotton bed spread with an incredible peacock print created via block printing. It is large enough to create a dress, skirt, and multiple tops, all for $6.99.

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Why Is Everyone Dressing Like They’re in a Wes Anderson Film? http://clairewears.com/why-is-everyone-dressing-like-theyre-in-a-wes-anderson-film/ http://clairewears.com/why-is-everyone-dressing-like-theyre-in-a-wes-anderson-film/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/why-is-everyone-dressing-like-theyre-in-a-wes-anderson-film/ When I wore a mustard yellow beret, a belted camel coat with oversized tortoiseshell buttons and loafers with mismatched socks to brunch last month with my friend David, he immediately…

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When I wore a mustard yellow beret, a belted camel coat with oversized tortoiseshell buttons and loafers with mismatched socks to brunch last month with my friend David, he immediately knew what I was doing. He looked at me and laughed and said “Oh, so you’re trying to channel the less troubled younger sister of Margot Tenenbaum?” I tried to protest – I didn’t want to look like I was channeling a character from a quirky independent film, I just really loved the outfit – but before I could get the words out of my mouth, I caught sight of myself in the window of the restaurant. I couldn’t believe it – he was absolutely right. All I would need to do to complete the transformation was frame myself evenly and add a completely deadpan expression. I had accidently Wes-Andersoned myself.

And I’m not alone. Look at your Instagram feed or walk through certain neighborhoods in major cities (Greenpoint, I’m talking to you!), and you’ll see them instantly – people dressed like they’re waiting for a vintage train to take them to a precocious spelling bee at a pastel colored resort run by Bill Murray. They wear berets and barrettes, knee socks with loafers, tweed blazers with elbow patches and round wire-rimmed glasses. Their colour palette stays inside a very small range of muted yellows, rust orange, forest green and burgundy. Everything is slightly too short or slightly too long. Nothing is ever regular sized.

The Wes Anderson aesthetic has broken free of the confines of film and has made its way into our closets and we can’t say we’re upset. However, we are curious. Why is everybody dressing like they’re trying out for “The Royal Tenenbaums: The Musical” all of a sudden? And why now, when Anderson has been creating visually distinct films for over twenty years?

“Fashion always draws inspiration from visual culture,” states Dr. Melissa Torres, a professor of cultural studies at New York University who teaches a class called “Fashion in Film.” “What is fascinating about the Wes Anderson influence is how specific and identifiable it is. You can point to somebody and say ‘that’s Wes Anderson core’ the same way you could say ‘that’s punk’ or ‘that’s prep.’ It has created its own distinguishable aesthetic category.”

The identifiable Wes Anderson look is based largely off of prep school uniforms, the colours and patterns of the mid-century, European sensibilities and vintage sportswear. It is at once nostalgic and timeless, whimsical yet precise, and different enough from other styles to be identifiable without being outrageous. While Anderson has been developing this aesthetic since Rushmore in 1998, it has only been in the past year or two that it has exploded as a mainstream fashion influence.

The timing makes sense when considering our current cultural environment. When the world can feel so chaotic and unpredictable, the carefully crafted and ordered world of a Wes Anderson film is appealing because it represents order, intention and the idea that there is someone directing the scene with precision.

“There is something reassuring about the control in Anderson’s aesthetic,” states Maya Lin, a costume designer who has worked on several independent films. “Every detail is thought out. There is nothing accidental. We have been living in a time of great uncertainty – pandemic, politics, climate etc. – and there is something soothing about looking like you fit into a world where everything has its place.”

TikTok has also been a significant factor in the spread of the aesthetic. The hashtag #WesAndersonAesthetic has over 500 million views. Users share images of outfits, home decor ideas, and scenarios where they imagine their lives as a Wes Anderson film. The algorithm pushes the video to anyone who has expressed interest in vintage clothing, independent films or quirky personal style, thus creating a self-reinforcing circle of Anderson inspired content.

Additionally, in 2023, TikTok users began filming mundane locations – laundromats, libraries, convenience stores – in a symmetrical and colour-coordinated style, similar to Anderson’s cinematography. Suddenly, everyone was viewing the world as if they were watching a Wes Anderson film. Fashion followed.

However, the Wes Anderson aesthetic is not just about nostalgia or escape – it’s about creating characters. Anderson’s films are filled with immediately recognizable characters who define themselves by their distinctive wardrobes. Think Margot Tenenbaum’s Lacoste dresses and blunt bob, Suzy Bishop’s pink dress and binoculars in Moonrise Kingdom, or the matching uniforms of The Grand Budapest Hotel. Each of these characters knows who they are and dresses accordingly. In a time when many of us feel lost and unsure of our own identities, that confidence is appealing.

“When you incorporate elements of the Wes Anderson style into your wardrobe, you’re essentially costume designing your own character,” states Torres. “You’re saying, ‘this is who I am in the movie of my life.’ This is a way of using clothing as a method of telling your own personal story.”

I can relate to this. Sometimes, when I feel especially uncertain or anxious, I reach for clothing that feels more intentional, more structured. Clothing that feels like armor against chaos. My most Wes Anderson-esque items (the mustard beret, a tweed blazer from a vintage store in Paris, saddle shoes I purchased on a whim and wear far more often than I anticipated) provide a feeling of being the main character, whether I’m walking down the street or sitting alone in a coffee shop.

Recently, I decided to attempt to emulate the aesthetic more intentionally, instead of accidentally. I wanted to explore how I would feel when I deliberately embodied the look. So, I put together a full-on Wes Anderson inspired outfit, including a pleated tennis skirt, knee socks, penny loafers, a button-down shirt with a Peter Pan collar, and a cardigan draped over my shoulders. I finished the outfit with a velvet headband and a pair of glasses. Overall, the combination felt like a cross between the image of a precocious private school student and an eccentric young widow with a dark secret.

The reaction was instant and varied. The barista at my local coffee shop, who typically ignores my existence except to serve me my coffee, smiled and said, “I love your entire vibe today.” A woman on the subway asked where I purchased my skirt. My editor, when I arrived at our meeting, simply said, “Rushmore?” and I nodded. That was it.

However, the most surprising result was the way the outfit affected how I moved through the world. I found myself standing taller, speaking more deliberately, and – I swear this is true – I experienced a strong urge to position myself in the centre of doorways and gaze pensively into the middle distance. The clothes did not just function as clothes – they directed me to portray a particular character in the film of my day.

“That is the true value of aesthetically distinct looks like Anderson’s,” states Lin. “They are not just visual – they are behavioral. Clothes make demands on how you move and interact.”

Of course, not everyone can or wishes to emulate the entire Wes Anderson aesthetic in their daily lives. The aesthetic requires a willingness to abandon practicality (knee socks are not the ideal choice for most office environments) and may venture into costuming territory if carried to extremes. Many people, however, are incorporating elements of the aesthetic into their wardrobes in more subtle ways – a pair of round glasses, a whimsical brooch, or simply a more thoughtful consideration of colour coordination.

“You don’t have to wear head-to-toe Margot Tenenbaum,” suggests Parker Lee, a stylist who has worked with several indie musicians who are embracing the aesthetic. “It’s more about the spirit – a little whimsy, a little nostalgia, and clothing that tells a story about who you are.”

High-end fashion has also taken notice of the trend. Miu Miu’s recent collections could easily dress an Anderson film, with their blend of vintage-inspired silhouettes, quirky accessories and distinctive colour palettes. Under Alessandro Michele, Gucci has adopted the eccentricity and layered storytelling inherent in Anderson’s visual universe. Even more minimalistic brands such as The Row have adopted elements of Anderson’s precision and intentionality – although not his whimsy.

However, the most creative interpretations of the aesthetic are emerging in vintage and second-hand communities. Since Anderson’s own visual references draw primarily from earlier eras — the 1960s, 1970s and 1980s — shopping for vintage clothing is the perfect means of gathering authentic Anderson-inspired pieces.

“My best Anderson-inspired pieces are all vintage,” affirms Lee. “A 1960s Pendleton jacket, a pair of saddle shoes that were made in the 1970s and still have tags attached, French school girl barrettes from the 1980s. They have the patina of actual experience that makes them feel like character pieces rather than costumes.”

Additionally, the connection to vintage and second-hand clothing provides a sustainable aspect to the trend that appeals to environmentally-conscious consumers. If you are going to dress like you are in a Wes Anderson film, it makes sense to gather those items in a manner that resembles gathering pieces for a film wardrobe – searching out unique items with histories as opposed to purchasing fast-fashion knock-off versions.

Lastly, there is something democratic about the trend. Like some high-fashion aesthetics that rely on specific body types or considerable financial resources, the Wes Anderson aesthetic is available to most people. Characters in Anderson’s films come in all shapes, sizes, ages and genders and many of the most iconic pieces – berets, glasses, Oxford shoes – can be found at a variety of price points.

“It is one of the only aesthetics that does not appear to focus on traditional notions of physical attractiveness or sensuality,” notes Torres. “It focuses on expressing a personality rather than showcasing the body, which allows it to include a wide range of people in a way that many trends cannot.”

As with any trend that achieves mainstream success, a backlash is beginning to emerge. Long-time fans of Anderson are concerned that the aesthetic is becoming diluted or misinterpreted by casual followers. Other critics argue that what appears to be whimsical and charming on some people can be interpreted as eccentric or odd on others, particularly older women or people of colour.

“Clearly, there is a level of privilege in being able to express quirkiness and have it seen as charming as opposed to bizarre,” admits Torres. “For example, the same outfit that would make a young white woman look like she is a sweet and lovable Wes Anderson character, would likely cause an older woman or person of colour to be viewed as unprofessional or odd. That is not Anderson’s responsibility – it is a fact of how these aesthetics operate in society.”

While this backlash presents valid concerns, I truly believe that the Wes Anderson fashion influence has the ability to positively contribute to society.

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I Wore Y2K Fashion to the Office and My Boss Said THIS http://clairewears.com/i-wore-y2k-fashion-to-the-office-and-my-boss-said-this/ http://clairewears.com/i-wore-y2k-fashion-to-the-office-and-my-boss-said-this/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/i-wore-y2k-fashion-to-the-office-and-my-boss-said-this/ I woke up at 6:30 AM, Tuesday, to a fashion crisis. I was standing in front of my closet staring at the same tired pieces I’ve been wearing for years.…

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I woke up at 6:30 AM, Tuesday, to a fashion crisis. I was standing in front of my closet staring at the same tired pieces I’ve been wearing for years. At that hour, I swear that everything I owned was ugly. I’d written multiple articles about the Y2K trend, and how young people seemed to have fallen in love with the horrible fashion choices I made in my youth. So, I said “forget it,” and pushed aside my neat, plain work clothes to dig through the “Nostalgia Box” I keep at the back of my closet. It’s a pathetic little time capsule of items I can’t bear to give away, but have no use for anymore – mostly from college and my early twenties, that miraculously have endured eight moves and each one of my numerous purges of my wardrobe. The bad news is, that is scary territory.
From the box I pulled out a pair of low-rise jeans. They were True Religion jeans. I know. I wasted stupid money on them ($180) in 2004. To me at 19 years old working part-time at a coffee shop, it was a fortune. The back pockets had huge stitches. Everyone thought they were super cool back then. I think I laughed the hardest.
Miraculously (or frighteningly), they still fit, although I did have to perform some serious contortionist maneuvers and deep breathing exercises. At one point, the button popped off and nearly hit my cat, Rufus. He shot me the worst look of disdain and then sulked off. Rufus is always my harshest fashion critic.
I paired the jeans with a light blue cropped cardigan that fell right above my belly button, a white baby tee underneath (it was free swag from a tech startup) and – I was completely losing my mind – I clipped back the front parts of my hair with butterfly clips. For a grand finale of real 2003-style, I pulled out a handbag shaped like a baguette that I had kept in pristine condition because it was too small to carry anything of value. It barely held my phone, keys and lipstick. Surprisingly, it fit the Y2K aesthetic perfectly – form over function, baby!
When I saw myself in the full-length mirror, I was briefly transported back in time. There she was – College Harper, the girl who believed Uggs were the ultimate innovation in fashion when combined with minis. Now, with the wrinkles around my eyes and the highlights that cost more than my first month’s rent in New York, I’m not exactly sure what I see in there.
Before I got into the rest of the article, I have to admit, I don’t work for a hipster design agency where people show up to work however they want. I work for Style Compass USA. We’re a fashion publication, but we still dress professionally. Our Editor-in-Chief Katherine consistently comes to our team meetings dressed in Prada. However, seeing myself in that ridiculous outfit somehow gave me a lot of confidence. Maybe it was the low oxygen levels from the tightness of the jeans.
Getting to the office was similar to participating in a social science study that no one else agreed to participate in. The security guard at the lobby desk double-checked me twice. The elevator ride was approximately 17 floors of avoiding eye contact with confused consultants from the financial firm below us. When I reached our floor, I was somewhat enjoying the minor disruption I caused.
The first person to notice me was Emma from the digital team. She coughed on her cold brew. “Harper. What. Are. You. WEARING?” she whispered-laughed and pulled me behind a pillar, as though we were co-conspirators in a clandestine fashion transaction. “Those… Oh my god, are those TRUE RELIGION JEANS?! Did you steal from a museum?! Or like, your own teenage bedroom?!”
“Research”, I lied. “That Y2K revival piece. Immersive journalism. I’m getting inside their heads.” This was a complete fabrication. The article was already finished. This was simply pure, mid-week insanity.
Emma looked both terrified and thrilled. “Katherine is going to have a heart attack. You know that, right?”
At no point had I contemplated Katherine’s reaction. Which I suppose indicates just how far gone I was that morning. Katherine Wang, our EIC, is a woman who once sent an intern home for wearing Crocs ironically. She is smart and supportive and has taught me practically everything I know about this business, but she also has strong feelings about what people wear to work. Nevertheless, the idea of Katherine’s disapproval only made the whole situation more thrilling. There’s something about hitting thirty that sometimes makes you want to burn it all down just to feel something. Or, I may have simply needed to add more hours to my therapy schedule.
By 10 o’clock, I had received 17 Slack messages, including “OMG YASSSS!” “Are you okay?” and “Do you need to talk to HR?” The features assistant asked if she could take a photo “for documentation purposes,” which I’m pretty sure meant to document the group chat I wasn’t a part of.
The morning editorial meeting was when things began to get really interesting. I sat in my normal seat, trying to ignore the fact that sitting down in low-rise jeans is essentially an act of public indecency. There isn’t an elegant way to do it. You’re always aware that the incorrect move can result in a plumbing-related incident that no one in a professional setting has given consent to observe.
Katherine entered the meeting room, three minutes late, in the middle of a discussion regarding the cover stories for next month, when she saw me. She stopped dead in her tracks, coffee cup suspended in air, and simply stared. The room was so quiet that you could hear the fashion assistants swallowing in unison down the hall.
“Harper,” she said finally, using that perfectly neutral tone that can signify either approval or dismissal, “that’s quite a bold choice for a Tuesday.”
I launched into my “immersive research” explanation again, adding a term I was fairly certain I created on the fly, “embodied fashion journalism”.
Katherine deliberately sipped her coffee, never breaking eye contact with my butterfly clips. Then, to everyone’s shock – possibly most of all mine – she smiled. Not her press conference smile that never reaches her eyes, but a genuinely human-looking smile.
“When I was 21,” she said, putting her coffee cup down, “I wore a denim mini skirt with a popcorn shirt and those Steve Madden platform sandals — you know the ones with the elastic straps? — to my first magazine interview.”

Everyone gasped. Katherine in anything other than impeccably-tailored designer clothing is like imagining the Queen in jogging suits.

“It was 2002,” she continued, “and I thought I looked incredible. The editor glared at me and said, ‘Darling, this is not Teen People.’ I almost died on the spot.” She paused, seemingly reflecting. “But she still hired me. Said anyone with the confidence to wear that outfit would probably have the chutzpah to cold-call celebrities for quotes. She was correct.”

I hadn’t anticipated Katherine telling a story and, definitely not one that humanized her in a way that left me feeling both more confident and less confident about my fashion disaster.

“I’m not suggesting I support this kind of behavior for client meetings,” she added, waving her hand toward my entire existence, “but it’s nice to remember where we came from. Trends in fashion come and go. All of the things you are currently wearing were fashionable at some point, then less fashionable, now fashionable again. Eventually, they’ll be unfashionable again.”

Then, quickly switching gears to discuss the feature lineup, as if nothing had happened, she left everyone looking a bit dazed.

By lunchtime, news of Katherine’s unexpected endorsement of my Y2K rebellion had spread throughout the office. Three of my coworkers told me they still had items from the era. One confessed to keeping a stash of Juicy Couture tracksuits that she refuses to get rid of. We tentatively discussed planning a “Y2K Friday” that will probably never happen, but sounded great to pretend about.

The biggest surprise came at 3 pm when my social media manager cornered me at my desk. “Wait there,” she commanded, snapping pictures with her camera. “This is pure gold. We’re doing a whole series on employees revisiting the trends they wrote about. Katherine already approved it.”

And that’s how my fashion catastrophe evolved into a six-piece Instagram series that generated more engagement than our Met Gala coverage. The comments section was a funny combination of “QUEEN BRINGING BACK THE REAL Y2K” from teens who were not alive during the original Y2K and “Oh my god no” from millennials who are still traumatized by whale tails and visible thongs.

Honestly, I lasted 9.5 hours in those jeans before I had to change into my backup emergency outfit stored in my desk (black pants and sweater, the fashion equivalent of witness protection).

However, for that brief time, I remembered something I had almost forgotten in the world of “fashionable attire” and “thoughtfully chosen silhouettes” – fashion should be absurd, fun, and generally useless.

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The ‘Embarrassing’ 2000s Trend Everyone Cool is Wearing Unironically Now http://clairewears.com/the-embarrassing-2000s-trend-everyone-cool-is-wearing-unironically-now/ http://clairewears.com/the-embarrassing-2000s-trend-everyone-cool-is-wearing-unironically-now/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/the-embarrassing-2000s-trend-everyone-cool-is-wearing-unironically-now/ To understand the rebirth of the baguette trend, we must look back at the origins of the baguette. The concept of a baguette was created in 1997 by Silvia Venturini…

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To understand the rebirth of the baguette trend, we must look back at the origins of the baguette. The concept of a baguette was created in 1997 by Silvia Venturini Fendi. She created a small rectangular bag that was meant to be used as a casual under-the-arm bag. This was a radical departure from the large tote bags that had previously dominated 90s fashion. The Baguette was catapulted to iconic status when Carrie Bradshaw declared it wasn’t just a bag; it was “a Fendi baguette” in a memorable 2000 episode of Sex and the City. Within short order, every girl with disposable income or access to Canal Street knock-offs had to have one tucked under her arm. By the mid-2000s, the style had trickled down to every mall store in America. Limited Too and Claire’s sold small purses with rhinestones and questionable phrases. Coach created monogrammed versions that suburban moms and daughters fought over. Paris Hilton never appeared in public without some iteration dangling from her bony elbow.

Then, like all ubiquitous trends, it died. Overexposed and the merciless fashion pendulum swing killed the baguette. Relocated to thrift stores and nostalgia-filled Instagram accounts documenting Y2K fashion disasters. We all moved on to large boho bags that could hold an entire days worth of supplies, to structured totes that said we were serious professionals, and to cross-body bags that allowed our hands to be completely occupied holding our iPhones in endless scrolling.

The baguette, however, became the symbol of dated and embarrassing – the fashionable equivalent of a lower-back tribal tattoo or overly plucked eyebrows. Something we all decided to collectively pretend never happened.

Now, fast-forward 20 years. Here we are – a professional fashion editor, watching with equal parts horror and fascination as the exact bag shape I once buried in boxes of old Y2K relics has become the hottest handbag silhouette among fashion insiders. The baguette – that small rectangle of fabric designed to fit nothing remotely useful — is back, baby, and ironically, not ironically. In a “Bella Hadid will not carry anything else” type of way.

So how did this happen? And more importantly, why am I starting to crave the same baguette shape I once mocked as the epitome of early-2000s fashion catastrophe?

Monica Chen, Accessories Director at a prominent fashion retailer explains, “This is the perfect example of the 20-year trend cycle. We’ve gone long enough since the early 2000s that Gen-Z does not associate the same level of embarrassment with these shapes as millennial women do. To them, it is a fresh and exciting look versus a cringe worthy one.”

That helps to explain why Gen-Z women are embracing this trend. But what about the rest of us – the women who vowed “never again” and are now willing to re-embrace the very same baguette shape we vowed to never see again?

Tyler Kim, Creative Director and Stylist for numerous A-list celebrities currently carrying vintage baguettes, provides insight. “There is something both nostalgically sentimental and practically appealing about these smaller bags. We have spent years lugging around large totes filled with anything we may possibly need, and then we realised, we mostly carry around our phone, wallet, and keys. The baguette is honest about what we actually need.”

In addition to the fact that many celebrities, particularly models and actresses, have begun to wear the baguette with an unusual sense of elegance, this trend has a significant impact on the way women view themselves. As Dr. Carolyn Mair, Fashion Psychologist notes, “Fashion is cyclical both aesthetically and politically. Women are returning to hyper-feminine accessories, which are typically associated with a time period when women felt pressured to dress in a manner that was perceived as more masculine or practical in order to be seen as serious.”

Dr. Mair continues, “The baguette represents a rejection of the notion that femininity and seriousness cannot coexist.”

Thus, for the women who participated in the initial baguette craze, embracing the baguette in 2020 requires a great deal of humility and humor. Recently, I found myself in the Fendi Store —for research purposes only, I swear — eyeing a purple sequined baguette that looked eerily similar to one I wore to a high school dance in 2004.

“The design you are referring to is a replica of a 2000 design,” the salesperson noted. “It has been extremely popular with our younger clientele.”

What is there to say about having your earliest fashion choices referred to as vintage? It is a peculiar sensation. Yet, I could not argue that the baguette looked remarkably modern when paired with the simple black blazer and jeans I was wearing – a far cry from the bedazzled outfit I paired with a similar baguette 20 years prior.

Jade Williams, Stylist for several celebrities currently participating in the baguette trend revival, suggests that the key to successfully incorporating a previous trend cycle into your wardrobe is context. “If you wear [a baguette] the same way you wore it 20 years ago, it looks like a costume. If you integrate it into your wardrobe, it becomes something new.”

This may explain why many women who were adamant that they would “never wear that again” (including myself) are tentatively adding baguettes back into their wardrobes. They are not pairing the baguettes with low-rise jeans and baby tees (although, that is another trend revival story altogether). They are pairing them with oversized tailored jackets, wide legged pants, chunky loafers, etc. All of which are decidedly 2020s.

If you are thinking about revisiting this trend, but are afraid you will appear to be wearing a costume from a “Y2K fashion disaster” themed party, Williams offers some practical advice.

“Choose a baguette in a solid colour or a discreet print instead of a version with a bold logo. Wear it with clean, modern pieces instead of piling on other Y2K trend pieces. Consider a baguette in a material that elevates it. A leather or suede baguette appears timeless whereas a canvas or velour baguette with a logo did not. ”

Authentic early-2000s baguettes are selling for two to three times the original retail price on the vintage market. However, the trend has also been democratized with a variety of price points available. For those interested in an affordable Y2K baguette experience, the resale market has many options. Small baguettes by Coach, Kate Spade, Dooney & Bourke, etc. that were once widely available in suburban malls are now available on Poshmark and ThredUp for under $100. Current season designer baguettes from Fendi, Prada, Gucci, etc. begin at around $1500 and skyrocket based upon the materials and embellishments used.

“This trend is unique because it is trending equally in both the luxury and mass markets,” states Chen. “Teenagers are buying $30 baguette-shaped bags at Urban Outfitters and fashion directors are purchasing four-figure vintage Fendi baguettes. The silhouette has widespread appeal.”

As for me, I have not purchased a baguette yet. I did find a small nylon mini purse from my “fashion memories” storage container. It was a plain black nylon mini purse that once held my Nokia phone and three Winterfresh gum sticks. Paired with a large boxy jacket and straight leg jeans, as opposed to its original mate (a truly hideous going out top I also found but quickly buried), it looked… strangely modern.

“We’ve gotten past the point of seeing anything from a previous trend cycle in isolation,” advises Williams. “When you pair it with modern, minimalist pieces, it becomes something new.”

Williams further explains, “Use the baguette as an unexpected contrast to your minimalist pieces. It adds an interesting visual element to an outfit. Use oversized silhouettes as a backdrop for a small baguette. It adds a nice contrast to your overall look. Use a baguette as a fun surprise in an outfit. It adds personality to your overall look.”

Williams concludes, “Ultimately, the key to wearing anything from a previous trend cycle is to give it a new perspective. It doesn’t have to be the same as it was 20 years ago. Give it a new spin and it can be relevant again.”

As I conclude this article, I am still hesitant to purchase a baguette. However, I did finally break down and purchase a vintage baguette from a local vintage clothing store. I paired it with a large, boxy jacket and straight leg jeans. The combination worked. It was a small victory. But I did it. And honestly, it was worth it.

For all the reasons discussed above, including the fact that the baguette is a great conversation starter, and the fact that it is a stylish and functional way to add a personal touch to an outfit, the baguette is worth considering. Whether you are a fashion risk-taker or simply someone who appreciates a well-crafted piece of history, the baguette is sure to bring a smile to your face.

And if you happen to find yourself in a similar situation as I did — questioning whether your formative fashion choices are truly a thing of the past — remember, it is okay to laugh at ourselves.

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The ‘Cursed’ Y2K Trends We Never Thought Would Return (But Here We Are) http://clairewears.com/the-cursed-y2k-trends-we-never-thought-would-return-but-here-we-are/ http://clairewears.com/the-cursed-y2k-trends-we-never-thought-would-return-but-here-we-are/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/the-cursed-y2k-trends-we-never-thought-would-return-but-here-we-are/ i still have nightmares about the low-rise jeans. not the somewhat cute, slightly hip-slung ones that brushed against the top of your hips—but the ones that sat about 3 inches…

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i still have nightmares about the low-rise jeans. not the somewhat cute, slightly hip-slung ones that brushed against the top of your hips—but the ones that sat about 3 inches below your belly button and made you a prisoner to constant vigilance and total avoidance of the normal human activities of sitting and bending over. the ones that caused the infamous “muffin top” on nearly everyone (except paris hilton circa 2003) and made thongs a necessary evil and lower back tattoos an entire identity.

“those will never come back,” i assured my assistant taylor when we were discussing cyclical trends in fashion. “some things are simply objectively bad ideas that we all collectively learn from. low-rise jeans are the equivalent of touching a hot stove—you only do it once.”

fast forward to last week when taylor sent me links to three designer collections that featured jeans that were so low-rise they were basically denim belts, accompanied by street style photos of gen z fashionistas sporting belly chains and visible underwear bands above their waistbands. the y2k revival i had been dreading had finally reached its most cursed final form.

“but…why?” i responded, honestly upset. “we worked so hard to escape those.”

“They look cute tho,” she shot back, with the breezy confidence of someone who was literally a toddler during the original low-rise era and therefore had no psychological baggage associated with them.

and that’s where we are now in 2025—we’re watching the full scale revival of the most questionable fashion choices from the early 2000s, led by a generation who only know these trends through old episodes of “the simple life” and their older sibling’s embarrassing facebook photos. what we y2k survivors referred to as fashion trauma, gen z refers to as delightful retro flair.

i’m not taking it well.

as someone who lived through the original versions of these trends—someone who owned the rhinestone encrusted going out tops, the layered tank tops, the teeny purses that could only hold lip balm and possibly one credit card—I think i am uniquely qualified to offer warnings to the dangers of these returning fashions. consider this less a trend report and more a survival guide from someone who has seen the fashion apocalypse and lived to tell the story.

let’s begin with the most contentious of the returns: the visible thong. also known as a whale tail (which alone should have disqualified it from ever being a trend), this look involved intentionally wearing your underwear up so high that it could be seen above your low-rise pants. thongs specifically—not just any underwear—because the early 2000s were obsessed with discomfort on a level that bordered on fanaticism.

the original version of this trend saw celebrities such as christina aguilera and halle berry walk red carpet events with bedazzled thong straps prominently displayed above their waistbands. the trend filtered down to high schools across america where girls would sit in class constantly readjusting their underwear to ensure it was visible enough. in hindsight, it was strange, uncomfortable, and probably broke several school dress code rules, but we did it for the culture.

the 2025 version is marginally more acceptable—designer dion lee has created what are essentially fake thong straps sewn onto pants, thereby eliminating the actual uncomfortably of the underwear component while preserving the aesthetic. other designers have incorporated visible straps into dresses and skirts as design elements rather than functional undergarments. it’s still questionable, but at least it’s an intentional aesthetic decision rather than a necessity driven by functionality.

if you are interested in attempting this trend, i recommend opting for pants that have visually interesting seaming or strappy details at the waistband. you’ll achieve the visual interest without having to justify to your grandmother why your underwear is showing at easter dinner. alternatively, reserve visible straps for beach days when they’ll be more contextually relevant with swimwear.

next in line of the y2k nightmare revival is the platform flip flop. not the regular flip flops that are perfectly suitable for summer footwear. no, i’m referring to the foam platform monstrosities that increased height by three inches and provided no ankle support. the shoes that went “slap slap slap” wherever you stepped. the footwear that loudly announced your entrance to a room before you’d even cracked open the door.

i had four pairs in different colours. naturally.

these orthopedic abominations have returned with a vengeance, championed by designers such as versace and steve madden (who, unsurprisingly, was also behind many of the original versions). the new versions have slightly better craftsmanship than the originals, however, they continue to be fundamentally impractical for any activity that requires greater exertion than standing completely still on a completely flat surface.

if you are considering adopting this trend, please choose versions that include an ankle strap. your future physical therapist will be eternally grateful. better yet, opt for the numerous stylish platform sandals that are currently available. these provide height without requiring you to constantly grasp with your toes to keep them on. fashion should not be an olympic event.

perhaps the most surprising y2k revival is the return of the going out top—that standalone shirt designed exclusively for nightlife use and would never, ever be worn outside of nighttime. typically, these shirts included a combination of satin, rhinestones, plunging necklines, and totally extraneous ties and straps. these shirts were designed to be photographed in dimly lit clubs before the advent of smartphones (thankfully).

today’s interpretation includes a focus on cropped silhouettes and interesting cut-outs rather than the bedazzled butterfly motifs and crystal lettering across the chest that defined the original. progress, i guess?

if you are thinking about attempting this trend, choose tops that have one statement element rather than 17 competing elements. a single interesting cut-out, an asymmetrical neckline, or a beautiful fabric can convey a lot of energy without crossing the threshold of “trying too hard”. and perhaps you want to ask yourself if your top really needs to include glitter text before you leave the house. (spoiler alert: it doesn’t).

no discussion of cursed y2k trends would be complete without mentioning the denim crimes. beyond the previously mentioned low-rise horrors, we are witnessing the return of additional denim atrocities: denim that isn’t blue (especially white and pastel shades that reveal everything), denim with odd embellishments (embroidery, rhinestones, inexplicable patches), and the most heinous of them all—wearing denim skirts over jeans. an actual layering choice that we collectively agreed upon and now have to admit to our fashion heritage.

“it looks cool in a vintage way,” taylor said with her typical confident air, when she arrived to work wearing a denim skirt over her straight leg jeans last month. she had paired it with a cropped cardigan and looked ridiculously good. as someone who wore this same outfit to my high school spring fling and felt like a denim wrapped potato, i was personally offended.

the main difference that i’ve begrudgingly accepted is in the styling. the current interpretations of these y2k trends are more balanced—the low-rise jeans are paired with oversized tops rather than crop tops, creating proportions rather than simply exposing as much skin as possible. the platform flip flops are worn with streamlined minimalist outfits rather than with every other trend at once. there is a thoughtfulness to the revival that was noticeably missing from the original chaos.

perhaps the most frightening y2k trend reviving itself is the return of the belly button ring, along with its partner-in-crime, the belly chain. these body adornments were ubiquitous in a time when midriffs needed to be visible 24/7 regardless of the temperature, the location, or the decency. i got my navel pierced on my 16th birthday against my mother’s direct orders, only to spend the next five years getting it caught on random items of clothing and eventually allowing it to close up after a particularly grueling encounter with a loofah that i won’t bore you with the details.

now belly button jewelry is back, with celebrities and models once again flaunting their abdominal piercing holes as fashion statements. the 2025 version features more refined and tasteful jewelry than the hot topic surgical steel barbells of yore, but the basic premise is identical—adorn your stomach hole for public viewing.

if you are over 25 and contemplating revisiting this trend, i beg of you to remember the recovery time, the irritation, and the reality that our metabolisms are not as active as they used to be. perhaps opt for a non-permanent belly chain instead? all of the y2k aesthetics without any of the permanence or risk of infection.

what fascinates me most about this y2k revival is watching how a new generation takes the elements of these trends and re-interprets them without understanding the cultural significance that defined them. they’re cherry-picking aspects without carrying the baggage of having lived through the whole nightmare.

“i don’t understand why low-rise jeans are such a big deal,” my 22-year-old niece explained to me recently. “they’re just jeans. if you don’t like them, wear something else.”

and that’s the critical distinction. the first time around, these weren’t merely fashion decisions—they were decrees. if you didn’t wear low-rise jeans in 2003, you simply weren’t participating in current fashion. there was a stifling lack of alternatives that made these questionable trends feel especially impossible to avoid. today, with fashion’s increasingly fractured and individualized landscape, these returning y2k elements exist as options among myriad others. they are a selection, not a mandate.

that being said, i still believe that some trends warranted to be left buried in the collective cultural graveyard. the ultra-thin eyebrows that took years to grow back for an entire generation of women. the bubble dresses that made everyone look like they were hiding a beach ball beneath their clothes. the ties worn as belts, a styling choice that continues to haunt me to this day whenever i view old photos. the chunky blonde highlights that turned us all into victims of an unfortunate accident with a bottle of hydrogen peroxide.

so, how does one successfully navigate this y2k revival without appearing to be dressed in a costume or, worst case, like you haven’t changed your wardrobe since 2003? the secret lies in both selectivity and modernizing. pick one y2k trend and combine it with modern garments. if you decide to attempt low-rise jeans (good luck, brave soul), pair them with a large, structured coat rather than a miniscule baby tee. if you are testing the waters with a going-out top, wear it with modern straight-leg jeans rather than the boot-cut denim of the original era.

also pay attention to the quality and type of fabric used. many y2k trends originated in fast fashion, made from materials that could only survive a single night out. the modern interpretations use superior materials, more thoughtful construction, and more flattering cuts. a satin top in a stunning jewel-toned colour combined with a modern asymmetrical neckline references y2k without screaming “i found this in a time capsule”.

and perhaps the most important thing to consider, is ignoring any trend that you disliked the first time around. fashion should be enjoyable and creative; it should not be a form of temporal penance. if low-rise jeans made you miserable in 2003, they will likely make you miserable in 2025. some traumas do not require re-experiencing.

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The ‘Unflattering’ Silhouette Fashion Editors Wear Anyway Because It Looks Cool http://clairewears.com/the-unflattering-silhouette-fashion-editors-wear-anyway-because-it-looks-cool/ http://clairewears.com/the-unflattering-silhouette-fashion-editors-wear-anyway-because-it-looks-cool/#respond Tue, 24 Mar 2026 19:02:36 +0000 https://clairewears.com/the-unflattering-silhouette-fashion-editors-wear-anyway-because-it-looks-cool/ In addition to the fact that I am going to be spending a large amount of money on this dress, I could tell my mom was also concerned about the…

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In addition to the fact that I am going to be spending a large amount of money on this dress, I could tell my mom was also concerned about the shape of the dress itself. It was a very long, very loose-fitting, and very boxy dress. It was made of a thick, stiff Japanese cotton that didn’t drape nicely over the body. Asymmetrical hems hit at the least flattering points on my legs. The neckline wasn’t particularly low-cut or revealing. It was just…there.

And yet, I was completely enamored with it.

But why wouldn’t I be? My mom pointed out that I have a “nice figure.” Why would I want to hide it?

This is a great question, and one that I’m having trouble answering without coming off like some pretentious fashionista. (Which, let’s be honest, I totally am.) How do you explain that sometimes, looking “great” in the classical sense is simply not the point? That sometimes the goal of aesthetics is to be interesting, unique, and unpredictable — not necessarily attractive?

The reality is that there is a huge disconnect between the advice mainstream fashion media gives us on what to wear (e.g. A-line skirts to emphasize your waist, V-neck tops to elongate your torso, wrap dresses that work on everyone), and what fashion insiders actually wear. Spend a few minutes walking around any industry event, and you’ll see editors, stylists and buyers deliberately choosing silhouettes that break almost every rule in the traditional style guide book.

For example, Simone, our infinitely chic fashion director, walked into our last editorial meeting wearing a gargantuan grey boiler suit that made her look as though she was reporting for duty at a particularly stylish nuclear reactor. She’s a slender woman, and conventional wisdom would suggest she should be in clothes that hug her curves. Instead, she chooses dramatic silhouettes that create negative space around her body. When I complimented her look, she just shrugged and said, “I like clothes that create their own shape rather than depending on mine.”

That’s the essence of fashion’s relationship with “unflattering” silhouettes – the notion that clothing can be architectural, conceptual and interesting in its own right – rather than simply providing wrapping paper for the body underneath.

I remember this shift happening in Paris during Fashion Week roughly five years ago. For years, every model on the runways wore skin-tight clothing. Suddenly, the most stylish women at Fashion Week were wearing what my mother would refer to as “bags” – oversized, drop-waist dresses with irregular hems, oversized jackets with oversized shoulders paired with baggy pants, and intentionally awkward lengths that cut across the widest part of the calf. None of them were attempting to highlight their “best features,” or disguise their “flaws.” They all looked cool. Not pretty. Not sexy. Not flattering in the slightest. Just cool – that indefinable quality that denotes fashion confidence rather than people-pleasing conformity to arbitrary rules.

After returning to New York, I started to notice this trend throughout the industry – the focus on interesting shapes rather than traditionally flattering ones. The design-forward silhouette had broken free of the runway and had made its way into the everyday wardrobes of fashion insiders. However, outside of our little bubble, regular women continue to receive the same tired fashion advice about dressing to create an hour-glass figure – regardless of their natural body type.

I found this disconnect fascinating. Why do mainstream fashion resources continue to promote conventionally flattering clothes when the actual fashion community has been doing things differently for years? And more importantly – what will happen if more women ignore those rules and choose to dress based on visual interest rather than maximum conventional body-enhancement attractiveness?

To clarify – I am not advocating that people try to look “ugly”. I am advocating for expanding our definition of what looks good beyond the narrow confines of “looks thinner”, “accentuates your waist” or “draws attention to your best assets”.

Simone summed it up perfectly in an interview I did with her for this article: “When someone says ‘this is unflattering’ – what they typically mean is ‘it does not make you look as close as possible to the current beauty standard’. But why should that be the ultimate goal of how we get dressed? I would prefer to wear something that expresses creativity, sparks thought, and initiates conversation. Pretty is easy. Interesting is a whole lot harder to obtain.”

And she is correct. Increasingly, fashion insiders are choosing interesting over easy.

Think about the recent obsession with anything drop-waisted – dresses, skirts, pants with waistlines at the hip, rather than the natural waist. According to conventional wisdom, this silhouette is universally “unflattering” because it does not hug the body where it is naturally narrow. Yet, it is everywhere in fashion circles – because it is fresh, slightly wrong in a deliberate way, and clearly indicates that the wearer values design over desperate attempts to appear thin.

Or consider the mass-produced, large, boxy blazers paired with barrel-leg jeans – a combination that is a direct contradiction to every rule concerning “proportion balancing” and “waist defining.” This silhouette completely ignores the old idea that you need to wear something fitted to counteract something loose. Rather, it creates a deliberately oversized shape from shoulder to ankle. On paper, this silhouette should look horrible. In practice, it looks ridiculously stylish – entirely due to the fact that it ignores those antiquated rules.

Last month, I hosted a panel entitled “Evolution of Style Perspectives” with three other fashion editors at a subscriber-only event in SoHo. Each of us arrived in essentially the same intentionally difficult silhouette: voluminous top, voluminous bottom, no waist definition whatsoever. During the Q&A portion of the evening, an audience member asked whether we actually wear these shapes for everyday use, or if they were merely for fashion events.

“This is literally all I wear now,” replied Katherine, Elle’s accessories director. “Once you release yourself from the constraints of thinking clothes should make you look a certain way, getting dressed is so much more imaginative and enjoyable.”

Katherine is far from alone. My Instagram feed is filled with fashion people embracing proportions that would be deemed errors by virtually every stylist in the world: mid-calf lengths that cut the leg at its widest point, oversized shirts with no discernible waistline, pleated pants with dropped crotches, etc., etc., etc. – countless examples of what my mother would categorize as “shapeless” dresses.

The resulting silhouettes may not be conventionally sexy, or even conventionally pretty. But they are compelling, unique, and intentional – all qualities that, to a fashion eye, convey significantly more style than looking visually appealing in the most obvious manner possible.

Of course, adopting these silhouettes requires a certain degree of self-confidence – especially since friends and family will often not comprehend the aesthetic decision. I’ve lost count of the number of times my well-meaning mother has suggested I “just add a belt” to the perfect, intentional sack dresses. Or how many times dates have appeared visibly perplexed by outfits that deliberately eschew conventional sex appeal in favour of creative proportion.

There is a distinct look men give when you arrive for dinner in architectural clothing rather than body-conscious clothing – a combination of confusion and mild disappointment, as if they believe you have misinterpreted the assignment. I’ve grown to appreciate that look. It verifies that I’m dressing for myself rather than for the simplest possible external validation.

That’s the greatest liberation associated with this shift toward the rejection of traditionally “flattering” clothing – moving the reason for getting dressed from the desire to be approved-of, to the ability to express oneself creatively. It is the difference between trying to look sufficiently pretty, versus trying to look sufficiently interesting. One is about meeting a standard. The other is about establishing a new one.

The irony is that once you begin embracing these “unflattering” silhouettes, they eventually become very flattering in a different sense. Not because they make your body appear in any specific way. But because they make you appear to be a person who understands fashion on a more profound level. A person who is confident enough to reject easy pretty in favour of something more nuanced and thoughtful.

Last week, I wore an especially architectural Comme des Garçons dress to an industry dinner – one of those conceptual pieces that deliberately distorts rather than “flattens” the body underneath. A few minutes after arriving, an editor from a major publication I admire greatly for its writing approached me specifically to compliment the dress.

“That’s a wonderful piece,” she said. “I love seeing women wear actual fashion – as opposed to just generic flattering clothes.”

It was probably the greatest compliment I’ve ever received regarding my style – recognition that I was using fashion as a medium for artistic expression – rather than simply as a means to enhance my appearance. And it was offered by a person whose opinion holds significant value within the industry. Not in spite of the fact that the dress was an “unflattering” silhouette. But because of it.

Incidentally, that dress is precisely the kind of piece that causes my mother considerable concern when she sees it in photographs. “Couldn’t you have found something that fit better?” she’ll text, and the worry is apparent even via the screen. At this point, I have stopped explaining to her that the objective of the dress wasn’t to conform to the conventional definition of fitting properly. The objective was to create a deliberate proportion – using clothing to create a shape that is aesthetically interesting rather than anticipated.

If you are intrigued by this approach, but have followed the conventional flattery-focused style advice for years, then beginning small is likely a smart idea. Try pants that fall at an unconventional length on your ankles. A jacket with a bit too big shoulders paired with something loose-fitting. A dress that doesn’t define the waist line at all. Not to conceal your shape. But to create a different one – a shape created by the garment – rather than by the body.

What you will likely discover is a different type of confidence. Confidence that is derived from creating an intended aesthetic choice – rather than from simply attempting to appear as skinny and pretty as possible. There is something profoundly subversive about rejecting the idea that women’s clothing should be, above all else, “flattering” in the most conventional sense.

As Emma, our sharp-as-a-tack style editor, succinctly put it to me while we were discussing this article: “Men can wear interesting silhouettes without anyone asking if the clothing is ‘flattering.’ Nobody asks if a man’s pants are making his butt look good enough. They simply ask if the pants look good as pants. I’d like to have that same creative liberty.”

She’s correct. The most stylish men in the fashion business wear pleated pants, oversized jackets and unexpected proportions without anyone questioning if they should wear something more flattering. The garments are evaluated as design pieces – not as merely body-enhancing vehicles.

That is the paradigmatic mind-set change behind fashion’s adoption of “unflattering” silhouettes – treating clothing as worthy of consideration in their own right, as opposed to simply as a means to create an optical illusion of an ideologically-idealized body-type.

Will this lead to us burning our wrap dresses and skinny jeans? Of course not. There is nothing wrong with wearing traditionally flattering clothing if it makes you feel good.

The issue arises when that is presented as the sole valid goal of getting dressed – where “flattering” becomes a restrictive constraint that stifles creative expression.

What the fashion insiders have adopted is the liberty to go beyond that constraint – to sometimes select interesting over conventional pretty, unique over traditionally flattering, and unpredictable over reliable. To view getting dressed as a creative act – rather than merely as a vehicle for presenting one’s body.

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This ‘Ugly’ Color Is Suddenly the Most Sophisticated Shade In Your Closet http://clairewears.com/this-ugly-color-is-suddenly-the-most-sophisticated-shade-in-your-closet/ http://clairewears.com/this-ugly-color-is-suddenly-the-most-sophisticated-shade-in-your-closet/#respond Tue, 24 Mar 2026 19:01:54 +0000 https://clairewears.com/this-ugly-color-is-suddenly-the-most-sophisticated-shade-in-your-closet/ I have a confession that may get me banned from the Fashion Editor Club. Until recently, I have owned ZERO BROWN CLOTHES. No chocolate, no caramel, no coffee, no nutmeg,…

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I have a confession that may get me banned from the Fashion Editor Club. Until recently, I have owned ZERO BROWN CLOTHES. No chocolate, no caramel, no coffee, no nutmeg, no cognac, etc. Just nothing. My closet is basically black, navy and the occasional electric blue that I pull out when I’m feeling wild. Brown has never really registered on my radar, or if it has, I’ve made a conscious effort to avoid it.

I could defend myself by stating that I’m from the 1990’s and during that time, brown was decidedly NOT COOL UNLESS YOU WERE A UPS DRIVER OR IN TO THAT “NATURAL GRANOLA” THING. My teenage fashion influences were Clueless bright plaid and Calvin Klein minimalism. While I was in fashion school, brown was that colour you used when you ran out of ideas – the sartorial equivalent of giving up. “Brown is for shoes and bags,” my first fashion director told me. “It looks cheap on clothes.”

How wonderfully WRONG SHE WAS!

Fast forward 15 years and I’m now in the midst of a career in fashion and I’m drawn to a colour I previously rejected as the most dull colour in the Crayola box.

Not just ANY brown, but a very specific shade of brown. One that I previously would have physically recoiled at the sight of: muddy, murky, slightly greenish brown. The kind of brown that has no sexy marketing name like “Espresso” or “Amber”. We’re talking ACTUAL MUD BROWN. The colour of, well, dirt.

This shade of brown first popped up at a Proenza Schouler show in February. They referred to it in the show notes as “Umber”, however my brain immediately categorized it as “Swamp Water.” To my surprise, instead of appearing drab and depressing, it looked CHIC. Elegant. Like liquid gold draped around the model. I spent several days after the show ruminating about that muddy brown suit. Which was definitely not the response I anticipated.

Then it appeared at Bottega Veneta. Then at The Row. Then suddenly it was EVERYWHERE — not just on the runway but on the coolest person at every industry event I attended this spring. My friend Emma is a stylist with an almost supernatural ability to predict trends. When she arrived at dinner in a muddy brown oversized sweater that made her look like she belonged in a high-end home furnishings catalogue, I commented on it. Her response? “It’s just brown,” she said casually, as if she hadn’t just taken the world’s most unexciting colour and turned it into a style choice.

The final nail in the coffin came when I visited my 68-year-old neighbour Diane. Diane is a textile designer who has been designing textiles for decades longer than I have existed. She answered the door wearing a muddy brown linen dress that made her silver hair look intentional. “Oh this?” she replied when I complimented her. “I’ve had this since the 70’s. Brown always comes back when people get tired of trying too hard.”

When she said that, it resonated with me. It perfectly summed up why this particular shade of brown feels so right for this moment. After years of dopamine dressing, vibrant maximalism and look-at-me fashion, there is something refreshingly rebellious about embracing a colour that refuses to draw attention to itself.

The next day I did something I’d never done before. I went shopping specifically for brown clothes. Not the safe browns – no camel, no chocolate, etc. I wanted that weird, murky, slightly unsettling brown that had haunted my fashion dreams. The sales associate at Dover Street Market actually LAUGHED when I described what I was looking for. “Oh you mean ‘Bog Brown,’” she said. “We call it that. It’s been selling out as soon as we get it.”

Bog Brown. PERFECT. Even the name sounds a little ominous – like stepping into something that could suck you under. And yet somehow it’s become the colour that sophisticated fashion people are embracing with great enthusiasm.

I left with a bog brown oversized button-down that cost more than my first month’s rent in NYC (Don’t tell my Dad – He still thinks fashion editors earn a living wage). I wore it to the office the next day. The responses were instant and telling. My 24 year old social media manager wrinkled her nose: “Is that…brown?” Meanwhile Katherine, our editor-in-chief who has impeccable taste and rarely comments on anyone’s appearance, came over to my desk to comment: “That colour is perfect on you.” I’ve worked with Katherine for 7 years and prior to this the most she’s ever commented on my appearance is “Nice Haircut” when I got an 8-inch cut last summer.

Since then I’ve become somewhat of a bog brown evangelist. I’ve gradually added pieces of this previously ignored shade to my wardrobe. A sweater here, a pair of wide-leg trousers there. Last week I went full commitment with a bog brown dress. My Mom described it as “Interesting” in the same tone she usually reserves for my dating choices.

What I’ve discovered is that this “ugly” brown is actually quite sophisticated simply because it’s so unexpected. It’s not attempting to be pretty or flattering in the traditional sense. It’s a colour that says “I’m not wearing this to impress you with how pretty I am.” There is a certain level of confidence to that choice that reads as immediately chic.

The trick to pulling it off, I’ve found, is to commit completely. This isn’t a colour that works as a timid accent piece. The bog brown cardigan I purchased and attempted to wear with my usual black jeans looked like I had shrunk a chocolate sweater in the wash. But the full bog brown outfit? Now I was getting stopped by fashionable strangers asking me where I got “that perfect brown”.

The other key is quality. Since the colour is so unassuming, the texture and fit become even more important. Cheap fabric in bog brown just looks sad, like something you’d find on the clearance rack in 1974. However, in a beautiful linen, a crisp poplin or a soft cashmere? It becomes the epitome of luxury. That’s why The Row has jumped on board this trend so enthusiastically – it exemplifies their quiet, money-whispering approach to fashion perfectly.

One of the most fascinating aspects of this trend is its universal flattering capabilities, despite being a colour that nobody would describe as “Pretty.” On my friend Jade, who has gorgeous deep brown skin, bog brown creates this beautiful tonal effect that looks incredibly polished. On Emma’s pale complexion, it adds warmth without being as harsh as black. My colleague Tyler, who has dark red hair that makes many colours appear garish on him, discovered that bog brown is one of the most flattering shades he can wear.

The secret is to determine the correct undertone for your skin. Bog brown can lean slightly greenish or slightly reddish. The greenish version typically works well on people with olive or golden undertones. The reddish version typically complements those with rosy or neutral undertones. The depth of the colour can also be adjusted – deeper for a more dramatic look, slightly lighter for a softer look.

I’ve also found that bog brown works surprisingly well with other colours. It pairs nicely with cream or ivory to create a subtle contrast that doesn’t have the harsh edge of black and white. It looks fresh with pale pink – not the obvious chocolate and strawberry combination, but something more sophisticated. And it pairs perfectly with that slightly acidic chartreuse that has been everywhere lately, creating a nature-inspired palette that somehow feels both organic and completely modern.

My favorite way to wear it is with different shades of itself – the brown-on-brown approach that feels like the 2024 iteration of the camel monochromatic looks that dominated a few years ago. There’s something so pleasing about the subtle transitions between slightly different browns, creating depth without obvious contrast.

The fashion industry’s acceptance of bog brown appears to be part of a broader movement toward what I’ll refer to as “anti-pretty” aesthetics. For a long time, fashion has been focused on enhancing conventional beauty – colours that bring out your eyes or flatter your complexion, silhouettes that emphasize or create curves in the “right” places. But increasingly, the most interesting fashion is challenging these very notions of what’s “flattering” or “pretty.”

Bog brown won’t immediately illuminate your face or cause strangers to exclaim over how gorgeous the colour is. What it will do is indicate that your relationship with fashion extends beyond the obvious. It’s a colour for people who are comfortable with complexity, who don’t need their choices to be easily understood or immediately appreciated.

Last week I wore my bog brown dress to an industry event and found myself standing next to a supermodel known for her bold, attention grabbing style.

She took a good long look at me and asked “Is that The Row?” (It wasn’t – it was a less expensive brand that I won’t mention because I wouldn’t want them to sell out before I can purchase another one). However, her question indicated something significant. Bog brown reads as expensive, as intentional, as fashion with a capital F.

If you are interested but hesitant to take the leap into the bog (Sorry – couldn’t resist), I would suggest beginning with accessories. A bog brown leather handbag provides all the functionality of black but feels more current. Bog brown boots work with everything but lack the obviousness of black. Even a bog brown scarf can provide an unexpected element to an otherwise normal outfit.

For the more adventurous, an oversized bog brown shirt worn open over a white tank and your favorite jeans is a relatively easy place to start. Or try a pair of bog brown trousers with a cream-colored sweater for a subtle twist on neutral dressing. As someone who began my brown journey just a few months ago and is now considering bog brown leather pants (Pray for my credit card), I can attest that this colour has a way of growing on you.

The benefit of this trend is that, like so many other fashion trends that feel exciting but ephemeral, bog brown has the potential to evolve into a long-term staple in your wardrobe. It’s not screaming for attention or bound to a specific cultural phenomenon that will rapidly date. It’s just quietly, confidently itself – the sartorial equivalent of the most intriguing person at a party who doesn’t need to speak loudly to be heard.

So here’s to bog brown, the colour I never thought I would love, the shade that defies conventional attractiveness yet somehow presents itself as the most sophisticated option in a world of obvious choices. At times the most compelling elements in fashion, as in life, are the ones that do not attempt to present themselves in the manner expected, but instead provide something more compelling – a form of beauty that reveals itself gradually, rewarding the second glance, the closer examination, the ability to perceive beyond initial impressions. And aren’t those characteristics what define true style?

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The ‘Ugly-Cute’ Shoe Trend Fashion People Can’t Stop Wearing Despite the Hate http://clairewears.com/the-ugly-cute-shoe-trend-fashion-people-cant-stop-wearing-despite-the-hate/ http://clairewears.com/the-ugly-cute-shoe-trend-fashion-people-cant-stop-wearing-despite-the-hate/#respond Tue, 24 Mar 2026 19:01:54 +0000 https://clairewears.com/the-ugly-cute-shoe-trend-fashion-people-cant-stop-wearing-despite-the-hate/ My brother looked at my feet during a family dinner and asked me, in a concerned voice, if I had injured my toe and needed a medical shoe. I told…

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My brother looked at my feet during a family dinner and asked me, in a concerned voice, if I had injured my toe and needed a medical shoe. I told him I hadn’t injured my toe and that I had paid far too much money for shoes that were made to appear as though I had hooves. His response was a mix of the same kind of pity you show to people who’ve joined some sort of cult. And I get that. There’s something cult-like about the fashion world right now when it comes to shoes that are made to mock everyone else.

Although ugly-cute shoes aren’t entirely new, since the 2013 resurgence of Birkenstocks, we’ve flirted with intentionally unappealing footwear. I believe the trend we see today is more extreme, more provocative. We’re no longer just discussing shoes that are functional or a little ugly. We’re discussing shoes that reject conventional notions of what’s attractive – shoes with abnormal shapes, shoes with abnormal proportions, shoes with unique textures, and shoes that could make a podiatrist cry.

About three years ago, I noticed the trend at Paris Fashion Week. As I walked through the crowds outside of the shows, I noticed that the fashion crowd had quit wearing their uncomfortable high-heeled shoes and started wearing shoes that looked as though they came from a senior citizen hospital ward or a deep sea diving expedition. There were the large rubber-soled Bottega Veneta boots that added six inches to tall models. There were the Balenciaga platform Crocs that looked like small boats. And then there were my personal favorites – the increasingly popular split-toe Tabi boots and flats that make your feet look like cartoon hooves.

As an example of investigative journalism (I’m guilty of succumbing to fashion peer pressure like everyone else), I chose to jump into the ugly-cute shoe trend.

Over the past year, I have accumulated a collection of ugly-cute shoes that my roommate has referred to as “shoes that will scare small children.” My current shoe rotation includes the aforementioned Hoka shoes that turn my feet into colorful marshmallows, the aforementioned Margiela Tabis that prompt comments from strangers asking if I’d injured my foot, platform fisherman sandals that add four inches to my height and make me walk like a baby giraffe learning to stand, and – possibly the ugliest – fuzzy Birkenstocks that look like I’m wearing muppets on my feet.

The responses to my shoe experimentation have been both fascinating and entertaining. Those in the fashion world either get it instantly or pretend to understand it out of fear of appearing foolish for not understanding it. My editor Katherine looked approvingly at my cloven Tabis and said, “very you,” which I’m going to take to mean that she thinks I’m becoming increasingly eccentric, as opposed to increasingly odd. My friend Emma, a stylist with impeccable taste, borrowed my platform fisherman sandals for a date and sent me a text message at 11 pm stating, “He couldn’t stop looking at my feet. Not in a positive way. However, I do think it was worth it.”

Those outside of the fashion world have offered opinions. After seeing my fuzzy Birkenstocks, my mother asked me, “Who hurt you?” A barista at my local coffee shop has nicknamed me “Boot Goat” every time I wear my Tabis. Additionally, a child on the subway pointed at my chunky trail running shoes and loudly asked his mother why “that lady is wearing her daddy’s shoes.”

Regardless of the ridicule, the confusion, and the occasional concerns over my mental stability and well-being, I have never felt more connected to my shoe collection. There is something fundamentally liberating about wearing shoes that reject the conventional concepts of attractiveness. It is a rejection of the male gaze, of the discomfort for the sake of sex appeal, of the idea that women’s shoes need to be dainty, pleasing, or feminine. Ugly-cute shoes represent the fashion version of not smiling at a strange man telling you to — a small, yet satisfying act of defiance.

Additionally, the trend reflects a broader shift in our perception of style. For decades, fashion was largely about enhancement — clothes and accessories that enhanced you, making you appear taller, thinner, sexier, prettier according to conventional standards. However, the most innovative fashion is about disruption rather than enhancement — disrupting conventions, experimenting with proportion, creating tension and visual interest rather than conventional attractiveness.

It is essential to note that there is a logic behind the madness. The most successful ugly-cute shoes are not random or unintentionally ugly; they are deliberately and thoughtfully ugly in a way that creates a visually appealing contradiction with the rest of your outfit. This is the central point that many individuals struggle to understand — these shoes are meant to be viewed as part of an entire outfit.

For instance, when I wear my Tabis with a simple black dress, the stark contrast between the clean lines of the dress and the bizarre, hooved-like shape of the shoes creates a visual tension that is more interesting than if I had worn standard issue strappy heels. When I pair oversized chunky loafers with a tailored pair of pants and a crisp button-down shirt, the proportional play creates a classic outfit that appears new and slightly subversive.

However, to successfully incorporate the ugly-cute approach requires a level of intentionality that separates it from sheer ugliness. The shoes should be obviously intentional, and not appear as though they were the result of an accident or mistake. One of the easiest methods of distinguishing between someone who understands this trend and someone who is simply riding the wave is to evaluate the remaining portion of their wardrobe. If the remainder of their wardrobe is equally unconventional and oversized and “wrong,” it may look like they’re dressing up as a character. However, when unconventional shoes are paired with more refined clothing items, that is when the magic happens.

I learned this lesson the hard way after I wore my platform fisherman sandals to a professional event with an oversized suit and chunky jewelry, and three separate people asked if I was “dressed up as a specific person” for a themed party that didn’t exist. Too much disruption without sufficient contrast simply looks like disarray. Currently, I follow what I call the “one weird thing” rule — if the shoes are the anomaly, keep the majority of the remaining portion of your outfit normal.

Those interested in the trend, but hesitant due to the extreme nature of the trend, have a variety of less extreme options that are unlikely to incite inquiries as to their foot health. The Birkenstock Boston Clog is almost mainstream at this point, and it has the same slight orthopedic quality to it that defines the trend. Oversized chunky loafers with exaggerated proportions create the aesthetic without the clown shoe aspect. Some New Balance styles (the chunkier, the better) can dip into ugly-cute waters while still being socially acceptable in non-fashion settings.

My friend Tyler, a financial advisor who can’t afford to dress outrageously for work, has developed a subtle approach. “I wear traditional black dress shoes, but if you look closely, they have extremely thick rubber soles that are slightly too chunky to be considered fashionable,” he said. “No one at the office recognizes it, but other fashion enthusiasts recognise it immediately.” It is like having a secret handshake with those who understand.

One of the greatest advantages of the ugly-cute shoe trend is that it is relatively democratic. Like many other fashion trends, there are few requirements in terms of body type or budget. Many of the most iconic ugly-cute shoes are quite affordable. While Birkenstocks, Crocs, and Hokas are undoubtedly not cheap, they are substantially more affordable than the alternative offerings of designers. Additionally, as comfort often contributes to the designs (although this is not always the case – my beloved Tabis require a breaking-in period that I can only describe as “character-building”), they are certainly wearable for real life.

This said, embracing the ugly-cute shoe trend necessitates a certain degree of self-assurance and a willingness to laugh at oneself. You must be willing to endure questions, comments, and possible ridicule. You must be willing to be able to honestly say that you don’t care if others consider your shoes ugly – in fact, you must enjoy it. This is a trend for those who dress for themselves and other fashion enthusiasts, not for general approval.

The first time I wore my platform fisherman sandals to my parents’ home, my father stared at my feet for nearly a full minute before inquiring if I had experienced “some financial troubles” because my shoes seemed to resemble “something from a discount store in 1974.” I informed him that they were in fact very fashionable and produced by a reputable designer. He continued to express skepticism. “Well, if you say so, honey,” he said in a tone typically reserved for those who claim to have seen UFOs.

But later that week, I watched him study them with genuine interest when he assumed I wasn’t paying attention to him. “I still think they are strange,” he said when I called him out on this. “However, I think they are interesting-strange rather than purely ugly-strange.” And that is the crux of the ugly-cute shoe trend – interesting-strange rather than simply ugly-strange. It represents the difference between thoughtless ugliness and deliberate, conscious disruption.

The trend has caused the fashion community to reflect. At a recent dinner party, a designer friend posed an interesting question: “What if we are all simply dressing ourselves up as the Emperor’s New Clothes? What if these shoes are not subversive or interesting – what if they are simply, objectively ugly, and we’ve all collectively lost our minds?”

There was a brief moment of unease before another guest replied, “Perhaps. Nevertheless, I appreciate how they look.” And that is essentially all that matters. Fashion at its best has long existed in the grey area between beauty and ugliness, convention and challenge. The ugly-cute shoe trend simply makes this conflict more apparent, more accessible, and more whimsical.

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The Under-$50 Basics That Look Just as Good as The Row (No, Really) http://clairewears.com/the-under-50-basics-that-look-just-as-good-as-the-row-no-really/ http://clairewears.com/the-under-50-basics-that-look-just-as-good-as-the-row-no-really/#respond Tue, 24 Mar 2026 19:01:54 +0000 https://clairewears.com/the-under-50-basics-that-look-just-as-good-as-the-row-no-really/ At the beginning of this article, I confess that I have a folder on my phone called “If I Won The Lottery.” Inside, I keep screenshots of clothing from The…

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At the beginning of this article, I confess that I have a folder on my phone called “If I Won The Lottery.” Inside, I keep screenshots of clothing from The Row. I don’t save pictures of homes, trips, etc. Only clothing. That may sound silly, especially since I am a 401(k)-owning adult. However, I do not think I am the only adult that has this type of fantasy.

The Row is a clothing company that makes the types of pieces that cause you to wonder if you have lost your mind for wanting something that looks like a completely normal white button-down. They sell a $350 t-shirt, $900 trousers, and $1,500 sweaters. The Row embodies that particular type of stealth wealth that whispers, rather than yells. The fabrics used by The Row are of the highest quality. The cuts are precise. When you wear a piece of clothing from The Row, you appear to say “this old thing?” as if you carelessly threw it on. In reality, the ability to pull off the effortless, “oh this old thing,” requires a trust fund.

Or does it?

Over many years, I have studied The Row’s aesthetic with the fervor that most people study possible partners or moles. As such, I have come up with a theory. What makes the pieces of clothing from The Row look expensive is not only the quality of the materials (although the Italian cashmere certainly helps). It is the proportions. The details. The silhouette.

As someone who cannot afford to spend $300 on a t-shirt or $1,500 on a sweater, no matter how well it fits, I have spent years searching for affordable pieces that mimic the aesthetic of The Row.

My salary as a fashion editor affords me the opportunity to purchase designer pieces every now and then. However, even I cannot justify spending three months’ rent on a cashmere cardigan, no matter how beautifully it hangs. Therefore, I have become a type of minimalist luxury detective. I search for alternatives to designer pieces that provide the same aesthetic hit without the financial regret.

Before I begin listing affordable pieces that provide the same aesthetic as the pieces of clothing from The Row, I want to make it clear. I am not saying that these affordable options are equivalent in quality to the pieces from The Row. The Row uses high-quality materials and craftsmanship that justifies their higher prices. I am saying that I have found affordable options that provide the same aesthetic.

Here are five affordable basics that provide the same aesthetic as The Row:

First: the perfect white t-shirt. A perfect white t-shirt from The Row costs approximately $350. It is made of the best pima cotton in the world. The cotton is grown by fashion angels. Or maybe it is just that the cotton is so good that it makes you wonder if you are dreaming. Regardless, the cotton is the best. However, I have found that Everlane’s organic cotton box-cut tee ($35) provides almost the same visual experience. The slightly boxy cut. The heavy weight of the cotton. The way it hugs your skin instead of clinging to it. All of these elements contribute to the idea that the tee was designed with intention, not accident. The collar doesn’t stretch out after two wear. The colour remains white. Are the two tees identical in quality? No. But when styled properly, no one will notice the difference but a fashion editor.

When choosing a white t-shirt, choose a slightly cropped, boxy silhouette. The sleeves should fall at the correct point on your upper arm. The neckline should sit flat on your collar bone without gaping. I buy mine a size bigger to get the perfect slouchy-but-not-sloppy look that is the foundation of the wealthy minimalist aesthetic.

Second: the oversized button-down. The Row sells an oversized button-down for approximately $950. The oversized button-down has the perfect amount of structure while also drape like liquid fabric dreams. However, Uniqlo’s extra fine cotton oversized long sleeve shirt ($40) is a surprisingly similar substitute. I have owned this shirt in three colours. I wear it every day. I wear it over jeans. I wear it as a light jacket. I wear it with tailored trousers. I wear it over slips. The cotton is stiff, but softens immediately after washing. The oversized cut is designed to be oversized. There is a distinction between a large shirt and an oversized shirt. The oversized button-down is the difference between looking like you are wearing expensive minimalist clothing, and looking like you just picked up whatever you could find in the mens department.

The things that make an expensive-looking button-down, expensive-looking, are the details. The placket should lay flat. The collar should have just enough structure to maintain its shape without appearing stiff. The overall proportions should look intentional rather than accidental. This is not just a large shirt. It is an oversized shirt. The line between looking expensive and looking like you dressed yourself in the dark is thin.

Third: wide-leg, full-length trousers. The Row offers an oversized wide-leg trouser for approximately $990. However, COS has perfected the high-street version with their wide-leg twill trousers ($49). The high waist. The perfectly straight wide leg. The way they break just above the shoe. These details create the perfect slouchy-but-tailored silhouette that is the hallmark of the aesthetic.

To create this look, find trousers that are wide, but not clownish. Find a rise that falls at your actual waist (your lower waist, your hips, your actual anatomical waist). The trousers should hug your body without clinging. The length should be tailored to your height. Yes, you will likely need to hem them. However, even with a $20 alteration job, you are going to end up with pants that look at least 10x more expensive than what you paid.

Fourth: knitwear. I have struggled the most to find true budget substitutes for knitwear. The Row’s knitwear is made of the finest cashmere. The pieces are priced accordingly. The Row’s cashmere pieces cost up to $2,000. However, Quince’s mongolian cashmere crew neck sweater ($50) is a surprising close to the quality of the Row. If you size up to create an oversized look, the Quince sweater is almost indistinguishable from the Row sweater.

There are three elements that define expensive-looking knitwear. The first element is that the knitwear should not pill. The second element is that the knitwear should weigh heavily. The third element is that the knitwear should hold its shape. Budget cashmere often looks sad after one season. However, with proper care (hand-wash cold, dry flat, store folded with cedar blocks), the Quince sweater will last you for at least two seasons. Will it have the same substantial hand feel as the Row? Probably not. But when styled properly, the Quince sweater will have the same visual impact as the Row sweater.

Fifth: outerwear. A slightly oversized blazer is a staple of the wealthy minimalist wardrobe. The Row sells an oversized blazer for approximately $2,350. However, H&M’s oversized jacket ($45) is a great, budget-friendly substitute. The slightly padded shoulders. The clean lapels. The single-button closure. The H&M jacket has all of the characteristics that define a blazer that looks expensive. I have purchased this jacket in both black and beige. I wear it constantly. Over jeans. Over slips. With tailored trousers.

The trick to finding a budget blazer that looks expensive is to look for clean lines and minimal detailing. No contrasting stitching. No decorative buttons. Nothing that draws attention to itself. The focus should be solely on the silhouette. Additionally, pay attention to the fit of the shoulders. They should extend slightly past your natural shoulder for that deliberate oversized look. Avoid the 1980’s power suit silhouette.

Sixth: accessories. I have become quite zealous about recommending Uniqlo’s airism seamless crew neck long-sleeve tee ($30). The second-skin fit makes it the perfect base layer under oversized pieces. It creates the proprietary tension between fitted and slouchy that defines the aesthetic. The seamless construction means that there are no lines interrupting the clean silhouette. I have purchased multiples of this tee. I wear them every day. Under everything. All winter.

In terms of accessories, the high/low mix is perhaps most evident to the trained eye. The Row produces some of the most desirable minimalistic bags. They produce them in limited quantities. They charge accordingly. The Row’s classic margaux bag sells for approximately $4,900. While I have not been able to find a $50 alternative that would deceive anyone, Mango’s leather shopper bag ($49.99) has a similar aesthetic to the Row’s.

Mango’s leather shopper bag is characterized by extreme simplicity. No logos. Minimal hardware. Clean lines. High-quality materials. While you may be able to find affordable leather bags that will develop a nice patina over time (as long as you avoid anything too trendy or decorated), saving up for a mid-range leather bag ($200-400 from a reputable brand like Cuyana or Polène) may be worth it. A quality leather bag paired with $35 t-shirts and $40 button-downs will elevate your entire look.

Styling Secrets.

While the above-listed basic pieces are inexpensive, there are ways to style them to make them look anything but.

Monochromatic Dressing.
Wearing the same colour family head to toe is the most effective way to make your clothing look expensive. I’m not suggesting that you have to dress entirely in beige (although, that is very Row), but creating a cohesive colour story – either all cool tones or all warm tones – instantly makes your outfit look intentional, therefore more expensive.

Embracing Unusual Proportions.
Another way to make your clothing look expensive is to wear clothes with unusual silhouettes. The wealthy minimalist aesthetic often combines a loose-fitting top with tight-fitting bottom or wide-leg pants with a fitted top. By combining deliberately unusual proportions, you are sending the message that you are making intentional choices with your clothing, rather than just putting on whatever is in front of you.

Proper Care Matters.
Budget clothing can look expensive if you take care of them. If you properly care for your clothing – no pilling, no fading, no wrinkles – you will look like you have money. Spending money on a fabric shaver, learning the best way to wash the different fabrics you have, and using an iron or steamer to remove wrinkles, will help ensure that your budget clothing looks like designer clothing.

Minimizing Accessories.
Finally, minimizing accessories is the final step to creating a look that is expensive. The Row’s aesthetic is never about accessorizing. A simple gold necklace or a pair of architectural earrings are sufficient. The focus should be on the clean lines of the clothing, not on distracting visual elements.

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