There are bad ideas, and then there are fashion editor bad ideas. Regular bad ideas are things like texting your ex at 2 AM or cutting your own bangs during a crisis. Fashion editor bad ideas involve public humiliation, physical discomfort, and usually photographic evidence that lives forever on the internet. This is the story of one such idea.
It was a Tuesday editorial meeting, the kind where we were all desperately pitching content for our “nostalgia issue” that wouldn’t just be another rehash of “Ten ’90s Trends We Love Again” (spoiler: it’s always slip dresses, Doc Martens, and scrunchies). We were knee-deep in a discussion about influential style moments when my colleague Marcus mentioned Kriss Kross, the early ’90s rap duo famous for wearing their clothes backwards.
“That was actually revolutionary,” he said, while everyone under 35 looked confused. “It completely subverted the expected function of clothing. It was fashion as rebellion.”
I must have had too much coffee that morning because before my brain could intervene, my mouth said: “I could try wearing my clothes backwards for a week. Like, as an experiment.”
There was a moment of silence, followed by my editor Catherine’s delighted laughter. “Perfect. File it by next Friday.” And just like that, I had committed journalistic malpractice against my own dignity.
For those too young to remember, Kriss Kross was a rap duo composed of Chris “Mac Daddy” Kelly and Chris “Daddy Mac” Smith, who shot to fame in 1992 with their hit “Jump.” They were 13 years old and had a very specific gimmick: they wore their clothes backwards. Not just their pants—everything. Shirts, jackets, hats, the whole ensemble reversed. It was bizarre, impractical, and completely iconic.
That night, I stood in front of my closet, reconsidering all my life choices. How exactly does one wear clothes backwards while maintaining a semblance of professionalism? I called Emma, my most brutally honest friend, for a consultation.
“You’ve finally lost it,” she said when I explained the assignment. “This is what happens when you work in fashion too long. Your brain breaks.”
“It’s for journalism,” I replied with dignity. “Also, Catherine already put it on the editorial calendar.”
“Fine. Button-downs are your best bet,” she said after some thought. “And maybe loose jeans? Anything with a zipper is going to be a disaster.”
Day 1: The Office Test
For my first backwards day, I opted for what I thought would be a relatively straightforward combination: a blue oxford shirt and straight-leg jeans. In theory, a button-down worn backwards should just look like a shirt with buttons down the back—quirky but not completely insane.
In practice, it was a nightmare. First, buttoning a shirt behind your back is physically impossible unless you’re a contortionist or have a willing assistant (I am not, and did not). I ended up having to button it first, then awkwardly shimmy into it like a straitjacket. The collar sat all wrong against my neck, choking me slightly when I turned my head. The chest area, designed for, well, a chest, gaped oddly at my back.
The jeans were worse. The front pockets were now on my backside, making it look like I had weird rectangular growths on my butt. The back pockets were in front, utterly useless and bizarrely placed. And then there was the button fly—now positioned directly over my spine and impossible to fasten without help.
“I need assistance,” I texted my roommate Zach, who found me contorted in our hallway, trying to button my pants using a combination of yoga poses and sheer determination.
“I’m not getting paid enough for this,” he muttered, but helped anyway. “You look deranged. Is this for work or have you joined a cult?”
The commute to the office was my first public test. On the subway, I caught at least three people staring openly at my backwards ensemble. One teenage girl nudged her friend and whispered something while they both giggled. A businessman in a suit gave me a wide berth, as if fashion rebellion might be contagious.
Walking into the office was worse. Our receptionist Marcel, who has seen me arrive in everything from runway-fresh conceptual Japanese designs to sweatpants on deadline days, actually did a double-take.
“You know your shirt is… nevermind,” he said, clearly deciding this was above his pay grade.
My colleagues were less restrained. “OH MY GOD,” shrieked Alicia from the beauty department when I walked into the kitchen. “It’s happening. You’re actually doing it. EVERYONE COME LOOK AT HARPER.”
Within minutes, I was surrounded by a small crowd of fashion people alternating between professional critique and unrestrained laughter. Our menswear editor suggested I needed a backwards baseball cap to complete the look. The accessories director wondered if backwards shoes were technically possible. The social media coordinator asked if she could please, please film this for our TikTok.
“Absolutely not,” I said, trying to maintain my last shred of dignity while everyone photographed me anyway.
The physical challenges became immediately apparent. Sitting was weird—the chair pressed uncomfortably against buttons never designed to be sat upon. The collar of my shirt kept choking me. The waistband of my jeans dug into my belly button. Worst of all, I had nowhere to put my phone, wallet, or keys, as all pockets were now inaccessible without dislocating my shoulders.
By lunchtime, I had a new appreciation for Kriss Kross’s commitment to their gimmick. This was genuinely uncomfortable, inconvenient, and embarrassing. When I mentioned this to Catherine, she smiled the particular smile of an editor watching her content plan come to life through a writer’s suffering.
“That’s what makes it a good story,” she said cheerfully. “No one wants to read about comfortable fashion experiments.”
Day 2: The Fashion Event
Day two happened to coincide with a press preview for a major designer’s new collection—the kind of event where editors and influencers judge each other’s outfits as ruthlessly as the clothes on display. Under normal circumstances, I would have worn something carefully chosen to telegraph fashion knowledge without trying too hard. Instead, I was committed to wearing a silk wrap dress—backwards.
If you’re wondering what a backwards wrap dress looks like, picture a hospital gown designed by someone who hates patients. The V-neck, now at my back, plunged uncomfortably low. The wrap closure, meant to be easily accessible at the side, was now somewhere near my right kidney. The hemline, cut to be slightly higher in front, was now higher in back, creating a mullet effect that no one has ever requested from a dress.
I enlisted Emma to help me get dressed, which involved a lot of cursing, safety pins, and eventually duct tape. “This is unhinged,” she kept saying, struggling with the wrap ties. “I can see your entire bra. And also most of your back.”
“That’s fashion,” I replied, with more confidence than I felt.
At the event, reactions split into clear demographics. The older editors looked concerned, as if I might need medical attention. The younger crowd recognized the Kriss Kross reference immediately and thought it was hilarious. The influencers, trained to spot potential viral content, circled me like sharks.
“Is this for a story?” asked a particularly famous fashion YouTuber, phone already out and recording.
“No, it’s my new signature look,” I deadpanned. “I’m calling it ‘reverse chic.'”
To my horror, she nodded seriously. “It’s very Demna,” she said, referring to Balenciaga’s creative director, known for subversive designs. “So brilliant.”
This was worse than being laughed at—being taken seriously for a ridiculous fashion choice is the true nightmare for anyone who actually works in the industry. I quickly clarified it was indeed for an article, but the damage was done. By the end of the event, I’d overheard at least two conversations speculating about whether backwards clothing would be “a thing” for fall.
The physical challenges of the backwards dress made the previous day’s difficulties seem trivial. Every time I reached for a drink or a canapé, I risked the entire garment coming undone. Sitting was a complex negotiation. Using the restroom required complete disrobing and then getting redressed with no mirror and limited mobility. I ate nothing and drank only what could be safely consumed while standing perfectly still.
Day 3: The Casual Weekend Look
For day three, I decided to tackle casual wear. Surely a t-shirt and jeans would be easier backwards, right? Wrong. A t-shirt worn backwards is just a shirt with a higher neckline in front and a lower one in back—awkward but not impossible. But the print on my vintage band tee was now illegible, prompting strangers to stare intently at my back trying to decipher the reversed lettering.
The real challenge came with outerwear. It was raining, and a backwards jacket is about as functional as a chocolate teapot. The hood covered my face instead of my head. The pockets were inaccessible. The zipper dug into my spine.
I had plans to meet friends for brunch, and their reactions ranged from secondhand embarrassment to genuine concern for my mental health.
“Is this a midlife crisis?” asked my friend Jake, who’s known me since college. “Because there are less public ways to have one.”
“It’s for an article,” I explained for what felt like the hundredth time. “I’m channeling Kriss Kross for a week.”
“The ‘Jump’ guys? Weren’t they like 12?”
“They were 13,” I corrected, as if this made my grown adult self emulating them any less ridiculous.
The waitress at the restaurant was too polite to comment directly but kept giving me sidelong glances while taking our order. When I went to the restroom, I overheard her telling another server, “There’s a woman here wearing all her clothes backwards. Table 7. No, I don’t know why.”
Day 4: Workout Clothes
By day four, I was developing a certain backwards expertise. I’d learned that anything with stretch was easier to manage. Anything with complex closures was a nightmare. Armed with this knowledge, I decided to attempt a backwards workout outfit for my morning Pilates class.
Leggings worn backwards are almost indistinguishable from regular leggings, except for the small pocket that’s now uselessly located on your lower back. A sports bra worn backwards, however, is just a band across your chest with cups awkwardly protruding from your back—not exactly supportive and definitely not designed for actual exercise.
I walked into the Pilates studio feeling slightly more confident than previous days, until my instructor Mia spotted me. She’s seen it all—clients in full makeup, inappropriate cutout leggings, people who insist on wearing jeans to class—but this gave her pause.
“Harper,” she said carefully. “Your outfit is… innovative today.”
I explained the article concept while setting up my reformer. She nodded slowly, then said, “Just be careful with the straps. I don’t want your clothes getting caught in the equipment.”
This turned out to be legitimate concern. Backwards clothes have all sorts of unexpected flaps, openings, and protrusions that can catch on things. Every movement became a potential wardrobe malfunction or safety hazard. I modified most of the exercises and spent more time adjusting my clothes than actually working out.
After class, a woman approached me in the locker room. “I love what you did with your outfit,” she said enthusiastically. “Is it a new brand? It looks conceptual.”
I couldn’t bring myself to admit it was just regular Lululemon worn incorrectly. “It’s European,” I said vaguely, then escaped before she could ask follow-up questions.
Day 5: Evening Wear
For my final backwards day, I had tickets to a gallery opening—the kind of event where fashion people actually dress up. This presented a new challenge: could backwards clothing ever be elevated to evening wear?
I selected a black midi dress with a simple silhouette, reasoning that backwards, it might look intentionally architectural rather than just wrong. I added statement earrings and heels, hoping the accessories would distract from the reverse neckline and odd draping.
Getting dressed required assistance again, this time from both my roommate and Emma, who had come over specifically to witness what she called “the grand finale of your public humiliation tour.”
“It doesn’t look terrible,” Zach said hesitantly, adjusting the backwards dress. “It looks… deliberate? Like maybe it’s supposed to be this way?”
“That’s the highest praise I’ve gotten all week,” I replied, genuinely touched.
At the gallery, surrounded by New York’s art and fashion crowd in their carefully selected outfits, I braced for more stares and questions. But something unexpected happened—people actually seemed to accept the backwards dress as a legitimate fashion choice. Several women complimented it, asking about the designer. A photographer from a street style blog asked to take my picture.
“It’s giving Margiela,” one fashion student told me seriously, referring to the avant-garde designer known for conceptual approaches to clothing. “I love how it challenges traditional garment construction.”
I wasn’t being laughed at anymore—I was being taken seriously, which somehow felt even more absurd. My backwards experiment had come full circle, from ridiculous to revolutionary, at least in the eyes of people primed to see meaning in fashion choices.
Later that night, I ran into Tyler, a designer friend whose opinion I actually respect. “Be honest,” I said after explaining the article premise. “Does this look completely insane or is there something here?”
He studied the dress thoughtfully. “Both,” he finally said. “It looks wrong in a way that’s interesting. The neckline being at the back creates a silhouette that’s genuinely unexpected. It’s not just a gimmick—there’s something architectural happening.”
I was surprised by how validating this felt after a week of feeling ridiculous. “So you think backwards clothes could actually work as a concept?”
“In a controlled way, yes,” he said. “Not literally everything backwards like you’ve been doing. But strategic reversal as a design element? Absolutely. Designers have been playing with that idea for years.”
He was right, of course. From Maison Margiela’s experiments with garment deconstruction to Rei Kawakubo’s structural innovations at Comme des Garçons, fashion history is full of designers who have reimagined how clothes relate to the body. Maybe Kriss Kross were actually fashion visionaries, not just kids with a gimmick.
As I concluded my backwards week, I found myself reflecting on what the experiment had actually taught me. Beyond the physical challenges and social awkwardness, wearing clothes in an unintended way forced me to think about why we accept certain clothing conventions without question.
Front and back, right and wrong—these are constructs we apply to clothing based on tradition and function. But what happens when you deliberately subvert those expectations? Sometimes you just look silly. But sometimes you create a new silhouette, a new relationship between garment and body, that contains a spark of creative possibility.
Will I continue wearing my clothes backwards? Absolutely not. The practical challenges alone—the inaccessible pockets, the uncomfortable seating, the inability to dress myself without assistance—make it unsustainable for daily life. Kriss Kross must have had a team of people helping them maintain their backwards aesthetic, or else they developed contortionist skills that I clearly lack.
But I might look differently at clothes now, more aware of the assumptions we make about how they should function. And I’ll definitely respect anyone brave enough to challenge those assumptions, whether they’re 13-year-old rap stars or conceptual fashion designers.
As for the forwards world, I returned to it with relief and a new appreciation for being able to sit comfortably, access my own pockets, and use the restroom without performing an escape act worthy of Houdini. Sometimes fashion is about pushing boundaries—and sometimes it’s about acknowledging that certain boundaries exist for very good reasons.
Now if you’ll excuse me, I need to go burn the memory of backwards jeans out of my mind with some regular, forwards retail therapy. I’ve earned it.