Gender Benders: Men Who Rock Women's Clothes

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

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)
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)
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)

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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)

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