Gender Benders: Men Who Rock Women's Clothes

Prince, Jaden Smith, Young Thug and more fashion mavericks.

/content/dam/betcom/images/2016/03/Celebs-03-01-03-15/031516-celebs-from-jaden-to-ej-gender-nonconformity-is-a-luxury-most-black-me-jaden-smith-ej-johnson.jpg

1 / 12

Fashion Without Borders  - Celebrities are known to push the envelope when it comes to style, and for some stars, that means blurring the lines of gender. While women have donned menswear for decades, these days, men are getting in on the gender-bending action. From the late OG Prince to the modern fashion risk-taker Jaden Smith, check out the men who fearlessly show that fashion has no rules.— By Moriba Cummings(Photos from Left: Stefanie Keenan/Getty Images for Beats by Dre,  Paul Natkin/WireImage)

Photo By (Photo: Nicholas Hunt/Getty Images, Bennett Raglin/Getty Images for SheaMoisture)

/content/dam/betcom/images/2016/09/Music-09-01-09-15/091416-Music-Young-Thug-Jeffery-cover-art.jpg

2 / 12

Young Thug - Gender bending in hip hop is a rarity, but for rapper Young Thug, it's second nature. On the cover for his album No, My Name Is Jeffery, the MC proudly rocks a dress. Though he became a meme sensation following the reveal of the cover, the rapper is standing by it proudly.(Photo: Atlantic, 300 Entertainment) 

Photo By (Photo: Atlantic, 300 Entertainment)

/content/dam/betcom/images/2016/01/Celebs-01-01-01-15/010416-celebrities-gender-benders-men-who-rock-women-clothes-jaden-smith.jpg

3 / 12

Jaden Smith  - Jaden Smith is known for being a free spirit, so his experimental fashion choices tend to be anything but surprising. From dresses and skirts to floral headbands, the young scion has worn it all, donning whatever he feels matches his mood. Sources close to the actor/musician say that he enjoys wearing feminine frocks because it makes a "high-end fashion statement." Proving that this sentiment isn't just in his head, high-end fashion brand Louis Vuitton made the actor the face of their Spring/Summer 2016 womenswear campaign. (Photos from Left: FayesVision/WENN.com, Nicolas Ghesquiere via Instagram) 

/content/dam/betcom/images/2015/07/Celebs-07-16-07-31/072815-celebs-lil-b-espn-cursed-or-not-cursed-2.jpg

4 / 12

Lil' B - The hip hop community is known for its forced hypermasculinity, but MC Lil' B has never been shy of embracing his feminine side. In his video for "Got the Mack Loaded," the rapper rocked a pair of dangling beaded earrings while serving his rhymes. This isn't the first time Lil' B has unapologetically worn clothing intentionally meant for women — it's now become a part of his brand.(Photo: ESPN)

SPL1254902_002

5 / 12

E.J. Johnson - Being the son of one of the greatest basketball stars of all time can't be easy to live up to. But E.J. Johnson has made a name for himself for his daring fashion choices. Ranging from oversize Birkin bags and furs to leather tights and stilettos, the Rich Kids of Beverly Hills cast member has it all and he rocks them with the perfect accessory: confidence.(Photo: JCalderon / Splash News)

ADVERTISEMENT
042015-Celebs-Boys-Who-Rock-Girl-Fashion-Jay-Alexander.jpg

6 / 12

Miss J. Alexander - The world first learned of Miss J. thanks to Tyra Banks's long-running competition series, America's Next Top Model. Dubbed the "runway coach extraordinaire," Miss J. has earned a following that has grown to respect him not only for his modeling expertise, but also his envelope-pushing outfits. From huge ball gowns to simple blue jeans, this reality TV judge mixes masculine and feminine fashion like the pro that he is.(Photo: Mark Mainz/Getty Images)

042015-Celebs-Boys-Who-Rock-Girl-Fashion-Derek-J.jpg

7 / 12

Derek J. - When you're one of the best hair stylists in Atlanta, you have to look the part — and Derek J. does just that. Known for refusing to wear anything "masculine geared," the Fashion Queens panelist is unapologetic about his fashion choices. From flow-y caftans on the beach to sky-high stilettos on the red carpet, Derek J. does not care for outside opinions, and it's hard not to respect that.(Photo: Brian Ach/Getty Images for Nolcha Fashion Week)

042015-Celebs-Boys-Who-Rock-Girl-Fashion-Miss-Lawrence-Washington.jpg

8 / 12

Lawrence Washington - Much like his Fashion Queens co-star Derek J., Washington — also known as Miss Lawrence — mostly wears clothing made with the female body in mind. The outspoken personality, who frequently appears on episodes of the Real Housewives of Atlanta, always complements his high-end looks with expensive accessories.(Photo: Blayze/Splash News)

042015-Celebs-Boys-Who-Rock-Girl-Fashion-Johnny-Weir.jpg

9 / 12

Johnny Weir - This bronze-medal-winning figure skater is known for his larger-than-life skating technique, and he always brings some of that flair to his style off the ice. When Johnny Weir steps out, he usually shows out in the highest of heels and the most dramatic ensembles. His androgynous fashion choices are as much a part of his brand as his impressive skating skills.(Photo: Ben Gabbe/Getty Images)

042015-Celebs-Boys-Who-Rock-Girl-Fashion-Andre-3000.jpg

10 / 12

André 3000 - While OutKast as a pair managed to push the envelope of fashion time and time again, it was André 3000 in particular who made that part of their image. From rocking a dress on the single cover of their hit "Ms. Jackson" to wearing his jeans high-waisted when most rappers sagged them low, Dre revolutionized fashion in hip hop. Nowadays, he is more conservative, but the rapper and actor definitely broke down barriers.(Photo: Arista, RCA Records)

ADVERTISEMENT
042015-Celebs-Boys-Who-Rock-Girl-Fashion-Prince.jpg

11 / 12

Prince - The earliest adopter of womenswear as men's fashion was undeniably the Purple One himself. At 5-foot-2, the "Purple Rain" crooner had become iconic for his signature platform boots, velvet capes and glitter-adorned frocks. Throughout the years, one thing remained consistent with Prince's fashion statements: the ladies love him just the way he is, and though he may no longer be here in the flesh, his influence in pushing the envelope undoubtedly lives on.(Photo: Frank Micelotta/Getty Images)

042015-Celebs-Boys-Who-Rock-Girl-Fashion-Jermaine-Jackson.jpg

12 / 12

Jermaine Stewart - Folks may remember this face from the late 1980s. His single "We Don't Have to Take Our Clothes Off" reached the top five in the Billboard Hot 100 and his fashion choices made everyone open their eyes to a new male aesthetic in music. Known for his pressed hair and colorful wardrobe, Jermaine Stewart paved the way for androgyny in music from a male's point of view.(Photo: Michael Ochs Archives/Getty Images)