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.
