I remember buying my first pair of women's jeans. It was around 2003, and I had an iPod full of music from The Promise Ring, Fugazi, twee-ass Matador Records artists, and a burgeoning selection of Def Jux and Stones Throw albums. At the time I worked at the Urban Outfitters in Georgetown, Washington, D.C. and had been looking for a pair of slim jeans that weren't bootcut, weren't expensive, and jet black (IT WAS MY EMO PHASE OK?!)

At the time, the slimmest Levi's offerings for men ranged from the slim-straight 514 to the slim bootcut 527. Of course, there was the pricey Levi's Premium line, which wasn't even selvedge but offered fits like the bootcut Skinner and the slim-straight Strummer, but even that wasn't skinny enough for my then-slender frame. Real heads remember the Offender jean, a low-slung low-rise jean that had the shortest, most ridiculous rise ever. I'm pretty sure the button fly had like, two buttons on the placket. So I ended up venturing to the women's section, where I ended up trying on a pair of Levi's 503s that offered a great skinny silhouette with the right amount of taper that I could rock with whatever Dunk SBs I was probably wearing at the time. 

people ​want to associate sexuality or masculinity with clothing, but none of those things have any correlation. —Matthew Henson, fashion editor, complex

Now, skinny jeans made specifically for dudes are commonplace. So long, practically useless front pockets! But at the time, during those days I was more ignorant about clothing, the women's jeans fit the bill—and my body. That's the thing about womenswear, it tends to predict how guys will dress in a few seasons. This whole fashion shit may seem absolutely superfluous to most guys, but Miranda Priestley is right—it really does trickle down to even the most sartorially clueless person.

Fast-forward about a decade later, and I'm attending my first Paris Fashion Week wearing 100 percent men's clothes, but looking at a bunch of womenswear. Virgil Abloh walked me through his second women's collection for Off-White, the "Nebraska" collection, which references everything from Raf Simons' Fall/Winter 2002 "Virginia Creeper" sweatshirts to the kind of woman from the Midwest who moves to the big city and undergoes a Carrie Bradshaw-like transformation. Except of course, the clothes were much swaggier than Carrie Bradshaw ever was. I still would rock the light denim trucker jacket with the fringe "WHITE" logo on the back. But as we talked about the difference between menswear and womenswear, the overarching point was that yes, it is totally possible for a man or woman to empower himself or herself through clothing.

So why do people still freak out about Young Thug preferring how women's clothing fits over men's? He recently admitted that about 90 percent of his clothes are women's, and sure—he wore a Gucci dress on the cover of Dazed, but most of the time it's indiscernible which rack Thugger's clothes came off of. When we interviewed him last year, he copped to wearing a long leopard-print dress as an elongated shirt, but addressed it pretty nonchalantly, as he should. Even Jaden Smith proudly bends gender lines with his style, throwing up a middle finger to outdated heteronormative fashion standards, captioning an Instagram photo with "Went To TopShop To Buy Some Girl Clothes, I Mean 'Clothes." Like Smith says, "it's about dressing a generation."

I asked our illustrious fashion editor, Matthew Henson, about the trend of more dudes shopping in the women's section these days, and if we even need to divide clothes by gender anymore. “The idea of men wearing women's clothing may be a bit hard for most people to become comfortable with, because people immediately want to associate sexuality or masculinity with clothing, but none of those things have any correlation,” he says.

He also pointed out that shops like Selfridges are putting gender neutral sections in stores, and that with men more subject the breakneck pace of trends in womenswear, he's witnessed guys getting clothing labeled for women in larger sizes. It's sort of like Secret deodorant. Yeah, it's branded for women, but using it won't throw your estrogen and testostorone levels off as a man.

“Style icons like Pharrell and Kanye have worn items from Céline, and they do so effortlessly,” Matthew adds, referring to West's patterned Céline blouse and Pharrell's ill pink Céline Crombie coat. Legendary designer Phoebe Philo may not have had men in mind when designing these pieces, but objectively, neither of them screams "I'm womenswear!" Fact is, the line between what men and women want to wear is only getting blurrier. And the idea of men in womenswear isn't as far-fetched as say, Gangstalicious' clothing line on The Boondocks, which aired seven years before Kanye West ever wore a Givenchy kilt.

It's not a new thing either. Barneys executive vice president Tom Kalendarian cited the '60s as a boom for gender-defying dressers with the Thin White Duke himself, David Bowie leading the charge. Remember the lyrics to "Rebel Rebel?" Bowie sings, "You've got your mother, in a whirl. She's not sure if you're a boy or a girl." And rock stars have carried that torch ever since. Dudes like Steven Tyler are known for dressing super flamboyantly while bedding numerous models and it's seen as rebellious masculinity. Not bad for an old man who shops in his daughter's closet.

The rise of egalitarian fashion is also another reason men and women are beginning to dress more alike. Sweden is one of the most gender equal countries on the planet, and it's home to a bustling fashion scene of its own, ranging from Nudie Jeans to Acne Studios. In fact, Acne's Fall/Winter 2015 menswear collection is all about gender equality, marketing clothing towards dudes emblazoned with patches that read "RADICAL FEMINIST" and "GENDER EQUALITY" while offering up the amorphous, androgynous silhouettes fashionable men and women currently have a predilection for. Oh yeah, and founder Jonny Johannson put his 11-year-old son in heels for the campaign imagery.

Acne Studios' Fall/Winter 2015 campaign featuring an 11-year-old boy in heels with a purse. FIRE. Image via Acne Studios.

“Women are always wearing men’s clothes, but nobody says anything about that,” says our editorial producer and noted fan of menswear, Emily Oberg. “No one is gonna call me a lesbian because I’m in head-to-toe men’s. It goes both ways, it should just be acceptable.” She notes that the uncanny valley of men in womenswear is when the clothing is obviously made for the female body, so see ya, peplum and A-lines. But now there are plenty of clothes that fall in that gray area, especially by labels like Vetements and Lemaire, and Lemaire's recent Uniqlo collaboration.

“When Céline was making slip-on sneakers for the first time, they were all the rage,” says Brian Trunzo, founder of men's shop Carson Street ClothiersMyself and many other men were looking for bigger sizes.”

Indeed, when Céline dropped its calfskin Air Force 1-like sneaker, a lot of male sneakerheads hoped it came in their size. But Trunzo thinks the whole menswear/womenswear thing isn't so much about gender politics as much as it is having a discerning eye. Fly shit is fly shit no matter who it's intended for.

A look from Vetements Fall/Winter 2015. THAT BOMBER THO.  Image via Vogue Runway.

“Lemaire does it extremely well. You can go to the showroom and not know at first glance if it’s a men’s or women’s collection,” he says. “I think it’s a matter of confidence, a matter of taste, and simply—what gets you going.”​

Maybe that's why when I got to shop Lemaire's Uniqlo collaboration, the items that caught my eye were a pair of pleated men's pants, a men's shirt jacket, and an off-white women's coat that makes me feel like a mixture of Patrick Bateman and Dexter from Dexter's Laboratory

“There’s a question to be asked: Is this even men’s or women’s clothing?” posits Trunzo, who for the record, thinks the coat is pretty ill.“Whether it’s labeled as men’s clothing or women’s clothing, if you find it cool you’re gonna wear it.”

 

The author in his Uniqlo & Lemaire women's coat.