A substantial portion of my closet comes from the men’s section. I have a collection of weathered, peeling leather belts I cherish, stolen straight from my dad’s closet. My oversized button-down collection boasts every color of the rainbow, striped and nonstriped. But possibly my most coveted garments are my jeans — I spent years building my catalog, and I can’t lie: I love my raw Japanese selvedge from eBay and my pair of ’70s-era Orange Tab Levi’s from Goodwill, to name a couple.

The thrift’s men’s aisle, in particular, is where the best denim lives: a true Levi’s 501, button-fly and straight through the thigh, or a 505, the zip-fly cut the company loosened by a hair in 1967, both draping over the shoe in a way the women’s counterparts have yet to break. Sure, the women’s “boyfriend jean” exists, but it’s somewhat of a licensing agreement for a markup. The 501 is just a jean.

Denim is only one entry point. The rest of the men’s rack has been migrating into my closet for years — oversized button-downs, pleated trousers, boxy knits cut for shoulders I don’t have — and the traffic has started running the other way, the men’s runways lifting silhouettes long filed under women. The shift isn’t one hemline or one shopper; it’s the silhouette coming loose from its formerly preordained genderization.

A brief history of ‘his’ and ‘hers’

The hard line between “his” and “hers” is younger than the department store that sells it, and about as principled.

Heels are the cleanest example: Elizabeth Semmelhack, senior curator at Toronto’s Bata Shoe Museum, has documented that the heel entered Western dress as men’s cavalry equipment — Persian riders needed heels to brace themselves in stirrups — and became a mark of male aristocratic rank under Louis XIV, who is not remembered as a man of restraint.

Only later was the shoe reassigned to women, with an added dose of discomfort.
Streetwear beat high fashion to it
Streetwear was built in the Black hip-hop community across the 1980s and into its 1990s golden age, and it was built big. The reigning silhouette was oversized on purpose — sagging denim, large graphic tees, Starter and puffer jackets cut for weather and volume rather than shape — and the labels that defined it sold that excess as the whole point.

The women of the era grasped the trade first. Aaliyah paired crop tops with men’s baggy pants and let the boxers peek out above the waistband; TLC turned overalls and denim into a uniform; Da Brat dressed, pointedly, like the men she shared the charts with; Missy Elliott sealed herself into an inflated black suit for her song “The Rain (Supa Dupa Fly)” in 1997, making shape itself the joke.

These women weren’t raiding a men’s closet so much as ignoring that it had been labeled one — degendering the everyday American wardrobe years before high fashion would sell the same instinct back as genderless or unisex. Count the overlap they normalized, most of it still ungendered on the rack today: baggy denim; jerseys; the baseball cap and its dressier cousin, the flat cap; Timberlands and other lug-soled boots; oxfords; loafers; button-down shirts.

However, this history is only half of the exchange.

Menswear crosses the aisle

Menswear, for its part, is raiding womenswear in broad daylight. Kendrick Lamar performed at Super Bowl LIX’s halftime show in flared, bootcut Celine denim and reopened a national conversation about a silhouette womenswear retired a decade prior. The heeled boot is returning to the foot that invented it.

Internet personality and filmmaker Eugene Lee Yang walked the 2024 Oscars in a red Walter Mendez skirt suit, its pleated train trailing from a men’s tailored blazer. The men’s purse has finally stopped being a punchline: for instance, A$AP Rocky’s cornucopian collection of designer bags.

The pretense that this shift is new does real harm. Queer and trans people have degendered their closets for as long as there have been societally imposed dress codes. The English stage has done the same since Shakespeare’s time, whose heroines were all boys in gowns — women being barred from the stage entirely.

Clearly, the practice is old, and the permission to cross these gendered lines has arrived late and unevenly.

Which begs the question: Why cross at all? The plain answer is that a gendered catalog halves your options for no practical reason; why deny yourself better-built denim and roomier cuts?

The more satisfying answer is that the most interesting, idiosyncratic looks come from mixing the two rather than choosing one — a lace hem under a men’s shirt, a jeweled choker over a suit. Don’t limit yourself to solely shopping where society and marketers expect you to.

How to assemble the look

Start with the denim, and buy it used. A vintage pair of Levi’s 501s or 505s, sized up until it stacks at the ankle.

Then, layer against expectation. A men’s oxford-cloth button-down, generously sized and half-tucked, with something textured underneath — maybe a lace hem, a slip skirt, an inch of eyelet at the wrist. Keep a graphic tee for warmer days.

Add a heel, and keep its history in mind while you do. A stacked Cuban-heel boot is not a concession to softness; it is menswear collecting a very old debt.

To accessorize, top it with a flat cap or bandana, and finish with a bag — bonus points if you embellish its straps.

Julia Ho is a senior writing about fashion history, pop culture and the shopping decisions in between in her column, “Confessions of a Shopaholic,” which runs every other Wednesday. She is also a chief copy editor and the staff development director at the Daily Trojan.