Young Thug

Young Thug is not interested in stereotypes. If he were, he would not have sported a pastel purple Alessandro Trincone dress on the cover of his 2016 mixtape, “Jeffery.”

The story goes that Thugger saw the dress in New York and, in a case of love at first sight, immediately wanted it for his cover. He has since joked that he had to wear the gown to conceal the AK-47 he had hidden beneath it, so one thing is clear: Traditionally feminine clothing is not a threat to Young Thug’s gangster image.

Lil Uzi Vert

Another member of the new school of semi-psychedelic, rock-influenced rap, Lil Uzi Vert is enigmatic and eccentric, like all great rock stars. And like all great rock stars, he’s not afraid to take risks with his look.

From his signature purple hair to his painted nails and studded accessories, Lil Uzi was a perfect choice for the 2019 Thom Browne Thanksgiving football game, where models and fashion icons dressed in the brand’s apparel for a photo-ready sporting game. Uzi himself sported a suit, tie, and skirt, grinning through the game like the definition of fashion and play.

A$AP Rocky

The ultimate pretty boy of rap, A$AP Rocky has been called the “Rihanna of Men,” the highest compliment in our book. Since he’s a self-proclaimed “Fashion Killa,” I like to attribute Rocky’s unapologetically daring fashion to being a New York City native.

From the outset of his career, the darling of the A$AP Mob has established himself as an innovator of men’s fashion. From frequent florals to pairing a shirt-dress with Timbs, this innovation comes from a place of boundary pushing.

Lil Nas X

Lil Nas X did not come onto the scene quietly and has not been quiet since. For that, we are eternally grateful. Rising to immediate superstardom following the controversy of his rap-country track “Old Town Road,” he made his red carpet season debut wearing a hot pink Versace leather cowboy suit to the Grammys and a silver sequined suit to the VMAs, complete with heels and a lace trimmed blouse.

A career launched by boundary pushing and criticism, Lil Nas X has not let public opinion deter his self expression. His recent Halloween costume is a testament to his all-in attitude, despite what the Internet might have to say.

Dressed in an exact replica of Nicki Minaj’s “Super Bass” jumpsuit and posing in front of an elaborate background, Nas donned full prosthetics and Nicki’s signature blonde and pink aesthetic to do the riskiest thing of all: come out as a Barb.

Yungblud

Another member of Gen Z, Yungblud is a certified punk rocker whose aesthetic frequently draws from the classic punk scene: black eyeliner, black nails, black hair, and the occasional black dress.

From fashion editorials to the stage, Yungblud doesn’t reserve his gender non-conforming looks for red carpets or photoshoots. He often jumps onto stage for one of his high-energy sets in a LBD and lipstick, making it a frequent part of his image and his no-care attitude.

With the last generation of pop-punk having been criticized for frequent sexism, it’s refreshing to see a prominent member of its resurgence bringing with him a clear message of dismantling gender norms.

Bad Bunny

Known for his genre-bending sound, Bad Bunny is playful and whimsical in all aspects of his art, but all with precise intention. His music often denounces toxic masculinity, and he has called it part of his platform to be an ally to the queer Latinx community in particular.

Part of his allyship translates to personally embodying his values, breaking barriers of gender as much as he can. Recently, he went full drag in his music video for ‘Yo Perreo Sola,’ a song about a woman who doesn’t need company to dance.

He also made a strong statement for trans rights on Jimmy Fallon in February, wearing a skirt and a T-shirt which read, “Mataron a Alexa, no a un hombre con falda,” — “They killed Alexa, not a man in a skirt.” The shirt refers to the media’s misgendering of an Afro-Latinx trans woman who had recently been murdered.

Bad Bunny exemplifies the ways in which some male celebrities are choosing to use fashion not just as a sphere of play, but also as an arena for protest.

Jaden Smith

No contemporary artist exemplifies this more than Jaden Smith, whose whole brand could have been centered around his identity as Will Smith’s son, but is instead focused on his … strangeness.

From esoteric tweets to famous girlfriends, Jaden Smith has made a name for himself in the media since he was a pre-teen. However, he has always used his platform to speak to a larger message.

After being vocal about shopping in the ‘woman’s’ section and wearing skirts to Coachella, he appeared in a campaign for Louis Vuitton’s 2016 women’s campaign. He’s been very vocal about why: First, he likes dresses. But mostly, he wants to use his relative privilege to be part of creating a new world with new conceptions of gender.

On Twitter, he said, “I’m taking the brunt of it so that later on, my kids and the next generations of kids will all think that certain things are normal that weren’t expected before my time.”

Jaden’s generational perspective calls back to the innovators in music before his time, who bore the brunt of it then.

Freddie Mercury

Of gender non-conforming boundary pushing, Freddie Mercury is a clear icon. His career surrounded by much press and speculation, Mercury’s defiant stage persona often instigated the media. But this didn’t deter him.

David Bowie

Another old-school British icon was David Bowie, whose cast of personas was routinely pushing boundaries. On the cover of his third album, The Man Who Sold the World, Bowie was pictured in a dress designed by Michael Fish, a mainstay in bold ’60s design.

Harry Styles has been long vocal about his love and admiration for Bowie, citing him as a major aesthetic and musical inspiration in his Vogue interview.

“I think with music it’s so important to evolve,” Harry says, “and that extends to clothes and videos and all that stuff. That’s why you look back at David Bowie with Ziggy Stardust or the Beatles and their different eras—that fearlessness is super inspiring.”

Prince

And to embody fearlessness as a male musician playing with aesthetic presentation is to harken back to the blueprint: Prince.

Prince’s widespread appeal is not one wrought out of easy-to-digest aesthetics or musical significance. Prince was actively political, actively experimental, and fearlessly unapologetic.