How These Celebrities Are Stylishly Breaking Gender Norms

The tyranny of menswear has been overthrown! While every guy should probably have at least one nice suit in their closet (you know, for job interviews), the days of gendered formalwear are over. With changing cultural attitudes about gender, what once was considered necessary to uphold a facade of strength and vigor is no longer relevant. What represents courage now is unabashed personal expression, regardless of outdated norms.

Given Hollywood’s liberal leanings, it’s not exactly surprising that celebrities are getting to these ideas before your average American. We’ve picked five celebrities who are blazing trails as far as personal style goes — and what we can learn from each one.

Timothée Chalamet

Timothee Chalamet Best Dressed
Photo by Axelle/Bauer-Griffin/FilmMagic

This young actor made his striking debut in the queer romance film Call Me By Your Name and, clearly, he learned something about the fragility of traditional masculinity. He’s since embraced the more femme aspects of his style without apology. Lately, when he’s not on the red carpet, he’s often seen in soft pink sportswear and athleisure or gentle acid-washed denis. But it’s his more formal choices that are the most striking: his stunning Prada jumpsuit at the 2020 Oscars became a mean-spirited meme, as all the best fashion does. But real sartorialists noted the simple elegance and perfect fit of the outfit, accented by the understated romance of the gilded brooch placed perfectly over his heart.

Chalamet’s interpretations of new masculinity for a time included the already outdated trend of wearing harnesses as avant-garde gear. Although that fad has come and gone, the lesson to be learned is that there’s nothing wrong with embracing queerness in your clothes, no matter how you identify. What once signaled effeminacy now points to confidence, which is exactly what everyone wants in a man.

Orville Peck

Orville Peck Best Dressed
Photo by Axelle/Bauer-Griffin/FilmMagic

He hasn’t quite burst into the mainstream just yet, but get ready to see Orville Peck literally everywhere within the next few years. More “serious” music people are quite desperate to dismiss this country crooner as an overinflated gimmick — and it’s true his masked buckaroo persona is certainly eye-catching — but his lushly melancholic lyricism and buttery smooth voice is undeniably charming.

As far as fashion goes though, Peck is a new deity in the gay yeehaw trend pantheon, taking his idiosyncratic luchador look and combining it with rhinestoned jackets and cowboy boots. His fashion is a perfect lesson in camp: more is always more, as long as it’s curated properly.

Peck’s outfits evoke mystery and lust, and although the average man certainly can’t afford equestrian couture, more adventurous dressers might benefit from eccentric accessories a la Peck, as long as you’ve got a real idea of the character you’re trying to portray.

Tyler The Creator

Tyler The Creator Best Dressed
Photo by Mike Marsland/WireImage

Tyler was a style god long before he started snatching Grammys. Known for his almost surrealistic combinations of confrontational streetwear, yuppie fashion, Wes Anderson-inflected color palettes, and transgressive haute couture, Tyler’s style game has elevated along with his steady rise to pop culture.

A lesson to be learned here is that shying away from notions of traditional masculinity is precisely what we should all be going for: Tyler’s not afraid to use bold, feminine color blocking when constructing his looks, pairing dressed down swimwear or skate gear with blazers or vintage tennis, and golf gear. The seemingly bizarre combinations work somehow and they tell a complicated story of class struggle by juxtaposing tropes of country club leisure with traditional urban accouterments.

Lil Uzi Vert

Lil Uzi Best Dressed
Photo by Mike Coppola/FilmMagic

The mall punk style that was excoriated by fashion critics in the late ’90s and early ’00s is now what rappers aspire towards, and Uzi is executing it perfectly. Leopard prints, leather motorcycle jackets, spiked chokers, and bondage pants — Uzi is taking Hot Topic to the next level, pairing traditional goth clothes with hip hop opulence. Think Pat Field, but then make it trap.

Remember, many of Uzi’s more counter-cultural signifiers were once seen as less than macho — I guess rightfully so, as punk fashion is the direct descendent of gay BDSM wear — but nowadays, they’ve been recuperated as symbols of anti-authoritarian strength.   But perhaps the most important detail here is that, as he brags on Instagram,Uzi doesn’t have a stylist. He’s picking out these outfits himself, meaning that he’s using his clothes as an extension of his creativity.

Billy Porter

Billy Porter Best Dressed
Photo by Axelle/Bauer-Griffin/FilmMagic

Speaking of throwing away normative notions of gender, Billy Porter has entirely transcended the binary. He’s lately been seen walking red carpets in full-on ball gowns, but always with a subversive twist, as shown in his tuxedo dress from the 2019 Oscars. There’s political purpose in these sartorial decisions, but there’s also a sense of newfound liberation that gives the looks emancipatory overtones.

“When you’re black and you’re gay, one’s masculinity is in question — I dealt with a lot of homophobia in relation to my clothing choices,” Porter told BBC in June. “I was trying to fit in to what other people felt I should look like … Putting on those heels made me feel the most masculine I’ve ever felt in my life. It was empowering to let that part of myself free.”

Because that’s the thing about only seeing menswear in one way: you don’t know the experiences you’re missing if you don’t ever try anything else.

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