Entertainment Music Gallery: Male Rappers in Women's Clothing Jaden Smith isn't the first rapper to wear women's clothing Share PINTEREST Email Print Bruce Webber/Louis Vuitton Music Rap & Hip Hop Top Picks Basics Rock Music Pop Music Alternative Music Classical Music Country Music Folk Music Rhythm & Blues World Music Punk Music Heavy Metal Jazz Latin Music Oldies Learn More By Henry Adaso Henry Adaso has written about hip-hop since 2005 and founded the award-winning blog The Rap Up. He has written for "Vibe," MTV, Rap Rehab, and more. our editorial process Henry Adaso Updated December 08, 2017 Jaden Smith inspired outrage and support in equal measure after being unveiled as the face of Louis Vuitton's womenswear. In the 1960s and 70s, men routinely dressed in what would be considered women's clothing today. In those days, men wore high heels and skirts or sarons. They wore dresses with belts. Fast forward to today, men in hip-hop are starting to challenge gender fashion norms. Gender-fluid style is gradually immersing hip-hop culture. Will Smith's 17-year-old son, Jaden, is one of those leading the charge. His sister, Willow, is a big supporter. Willow wrote a powerful statement on Instagram in support of gender fluidity: “Males and females are put into boxes of expectation when we are born. As we grow we start to raise the damages that those expectations cause to our spiritual and emotional understanding of ourselves and life. The more we start to realize that we are all the same and infinitely different at the same time, the more we begin to shed those expectations and live free to continue to uplift the essence of Earth.” Jaden isn't the only man who has ever traded pants for a skirt. Explore this gallery of male hip-hop artists in women's clothing. 01 of 05 Kanye West Kanye West. © Marco Torres In 2011, Kanye West and Jay Z touched down in Houston for the Watch the Throne Tour. The album and tour represented a merging of empires. Jay, the more traditional of the pair, wore standard hip-hop attire: baggy jeans and a fitted hat. Kanye, the free spirit opted for skinny leather pants and a leather Givenchy kilt. Both wore custom-made WTT tops. Unsurprisingly, West's outfit brought significant attention to the tour. It inspired a parody Twitter account along with some social media slander. Luckily for 'Ye, his style was Kim Kardashian-approved. 02 of 05 Young Thug Dazed Magazine Young Thug is a bit of an anomaly. His music conforms to standard rap tropes. His style, however, confuses and agitates hip-hop’s definition of masculinity. Thug uses his Instagram platform to flaunt his eccentric style: snug tank tops, skin-tight pants, and the occasional skirt. In 2015, Thug posed for a Dazed photoshoot in a Gucci lace top and Molly Goddard sheer tulle dress. Thug told GQ that “ninety percent” of his clothes are women’s. 03 of 05 Andre 3000 LaFace/Arista Andre 3000 stays fresh to death. On the artwork for OutKast's hit single "Ms Jackson," an ode to "mamas and baby mamas," Three Stacks is seen rocking a white dress. The song ended up winning a Grammy for Best Rap Performance. 04 of 05 Yasiin Bey (aka Mos Def) Yasiin Bey (aka Mos Def) wore a wrap during the 2014 Music Exchange 2014, at the Cape Town City Hall in Cape Town, South Africa. Michelly Rall / Getty Mos Def is one of the most fashionable rappers around. Mos, who goes by Yasiin Bey these days, showcased his adventurous style in a Ghanaian wrap at the 2014 Music Exchange. Naturally, Bey’s choice of attire led to an online debate. Is that a skirt, a futah, or some alien Illuminati garment? Who knows. What we know for certain is that Mos loves Africa, per his raving comment at the time: "I've been some places… some of the best places in Europe and the US. Amazing talents and amazing places. But no place is like Africa. No place" 05 of 05 Lil B ESPN Lil B has been challenging gender norms for years. It extends beyond his fashion. In 2011, he released an album and titled it . During an ESPN interview, the "Wonton Soup" rapper showed up in a lace blouse, sun hat and earrings. Twitter was abuzz with jokes. The Boombox article describing the outfit described included the phrase "Lil B Looks Like Someone's Grandma." That's a super stylish grandma.