When Kid Cudi appeared on Saturday Night Live in early April to perform two songs from his latest album, Man On The Moon III: The Chosen, it was his outfit that made headlines, not the music. Worn as a tribute to Kurt Cobain, who committed suicide during the same week in 1994, Cudi donned a custom white floral dress made by Virgil Abloh under his Off-White label. The similarities between Cudi's and Cobain's dresses were overt, although times have since moved on; appearing on the cover of The Face in 1993 in a David Sims image, a kohl-eyed Cobain wore a floral tea dress with a white T-shirt underneath. While the Nirvana frontman managed to marry grunge and granny chic together in a single look, Cudi's approach was more brazen. Offsetting the dainty straps of Abloh's sundress were the tattoos on Cudi's upper body - the dress was wholly at odds with the Ohian musician's usual, masculine gender expression (crop top Coachella moment aside). Cudi opted for a traditional curtsey at the end of his performance, while a post-show image of the SNL cast captures Cudi centre stage, flexing his muscles. 'Have it both ways,' he seemed to say.
'For me, it represents personal empowerment despite any social norm,' Abloh said of the dress in an interview with GQ. But, despite the dress, the response was not all rosy. British trans model and activist Munroe Bergdorf took to Instagram to applaud Cudi's gender-bending look, but also reminded us that, for LGBTQI+ people, wearing feminine clothes on a daily basis is often fraught with the possibility of violence. 'We need to bear in mind that where some are applauded, others are literally being heckled and scared to leave the house because of transphobic and homophobic violence,' she wrote.
Despite hip-hop being a notoriously homophobic musical genre, its frontmen have made great leaps forward in terms of gender non-conforming fashion. Renaissance man A$AP Rocky is known to favour a snug babushka, Frank Ocean strutted down the runway at his Paris Is Burning-themed 30th birthday party in bejewelled, sheer leggings, Lil Uzi Vert and Jaden Smith have both donned skirts (the former for Thom Browne, the latter for Louis Vuitton), and Tyler, The Creator has appeared in loud, form-fitting suits and a bowl cut, platinum blonde wig as his latest musical alter ego, Igor.
Across the recent A/W 21 season, designers also experimented with androgynous fashion for men. Molly Goddard sent a man out in a red tartan skirt (marking the British designer's first foray into menswear), while at Burberry, Riccardo Tisci had his male models in knee-length pleated skirts and kilts, worn underneath ultra masculine varsity jackets. Stefan Cooke opted for a racier vision, assembling an army of men in minskirts and tweed jacket mini dresses.
For decades, male models have appeared on the runway in dresses and skirts for designers including Vivienne Westwood, Yohji Yamamoto and Jean-Paul Gaultier. But, despite fashion imagery being hugely influential in terms of setting trends, at the end of the day, models are only playing dress up. In the same way that Bergdorf and other commentators threw shade at Cudi for wearing a dress as a one-off spectacle, disavowing the LGBTQI+ lived experience, fashion images of men in dresses are, for the most part, orchestrated images of gender ambiguity.
But, this doesn't mean we're not into them - merely, it's important to keep the fantasy aspect of feminine dress in mind. Years before Cudi wore his Off-White number, numerous male musicians have lent into more ambiguous modes of dressing; on album sleeves, magazine covers, on Instagram, and in fashion editorials. Below, we picked out five of our favourite occasions where men dared to don the frock.
When Young Thug appeared in an unbuttoned white shirt underneath a baby blue, cascading skirt, paired with a cocktail umbrella hat on the cover of his JEFFEREY album in 2016, the internet was shook to its very core. A trap musician in a floor-length skirt? Shocking. For a genre famed for its masculine bravado and misogynistic lyrics (both of which Thug engages in), this outfit went firmly against the grain. Thug spotted the Japanese-inspired look at the VFILES Runway Season 7 show, which was made by Neapolitan designer Alessandro Trincone. 'If I don’t get this for my cover I’m going to die,' he reportedly said at the time. In an interview for Tyrone Lebon's Calvin Klein ad campaign during the same year, Thug said, 'In my world, it don't matter. You could be a gangster with a dress, or you could be a gangster with baggy pants. I feel like there's no such thing as gender.' Many of his fans, as it transpired, did not agree.
Harry Styles's US Vogue December 2020 cover cemented the larky British pop star's sartorial status as a gender-bending king. Appearing in a silken Gucci tuxedo jacket and dress, and a suit paired with a Victorian crinoline and cream tutu by genderfluid designer Harris Reed, Styles adopted womenswear shapes for the Vogue shoot with alarming aplomb. The cover also made magazine history, marking the first time a man had ever appeared solo on the cover of US Vogue, which was a hefty statement in itself, but not everyone was pleased. American conservatives Candace Owens and Ben Shapiro took to Twitter to berate Styles' choice of dress. 'Bring back manly men,' wrote Owen. In a Guardian interview from 2019, Styles expressed his love of feminine dress. 'I’m not just sprinkling in sexual ambiguity to be interesting. I want things to look a certain way. Not because it makes me look gay, or it makes me look straight, or it makes me look bisexual, but because I think it looks cool.'
A year before the JEFFEREY album cover, Thug appeared in a dusty grey Molly Goddard tulle number for Dazed. The image was transatlantic - who would've thought Goddard's prim west London vision could mesh with Thug's brand of Atlanta swagger? Now, an essential anecdote. The accompanying Dazed profile of Thug chronicles the moment his sister kicked off at the sight of the Goddard dress. '“Take it off!” a woman’s scream announces, bouncing off the mansion’s marble walls. It’s Amina, Thug’s sister and day-to-day manager, alarmed at the sight of her sibling in a grey tulle dress with tutu skirt by Molly Goddard.“TAKE THE TUTU OFF, NOW!” Thug shrugs – he’s already posed for the shot.'
Despite being just 22 years old, Steve Lacy's musical back catalogue is extensive. After co-producing The Internet's woozy Ego Death (2015) album, he has since collaborated with artists including Kendrick Lamar, Tyler, The Creator, Kali Uchis and Solange. Lacy came out as bisexual in 2017, and has since leant into more ostentatious clothing. His best frocks have included a grey Comme des Garçons dress at the 2020 Grammys, an Opening Ceremony x Lacoste dress in the hallucinatory 'Playground' music video, and a check Balenciaga number, shot in - of all places - the shower. 'Sometimes you gotta tell your homophobic hyper masculine 41 year old cousin to shut the fuck up in front of your whole fam 😂 bitch ima wear a dress a purse some heels fuck you,' he wrote on Instagram.
Whether singing on stage with Blood Orange for the Negro Swan tour, collaborating with Shayne Oliver on his cult New York label Hood By Air, or singing sweet, gospel-infused funk on his latest album, AUNTIE, Ian Isiah oscillates between masculine and feminine fits with pure flamboyance. The Brooklyn native, also known as Big Shugga, has worn everything from a corseted green gown and matching wig in Blood Orange's Marie Antoinette-esque 'Benzo' music video, a phantom pregnant belly on the cover of office, and a sleeveless Santa Claus outfit in the Telfar X UGG commercial. 'I believe in love and no titles. And I believe in giving everybody a chance to go off. Pushing those boundaries in fashion first taught me I could push boundaries in general. I know the “no gender” thing is trending right now, but love is love,' said Isiah in an interview with Pitchfork.