Guys Who Wear Women's Clothes

See the men who have stepped outside the gender box.

Ladies Only? - Nobody bats an eyelash these days when a woman has crossed over into menswear, but these male entertainers have made headlines for their foray into styles that were once considered “only for the ladies.” But, we have to admit, when it actually fits well and looks fly, we’re not mad at it! (Photo: Vince Bucci/PictureGroup)
Lil Wayne\r\r - Little pants have become a big wardrobe favorite of Lil Wayne. After he wore a too-tight leopard variety at the 2011 MTV Video Music Awards, clothing brand Tripp NY has since confirmed what many fans already figured: the pair were actually sold as Women’s jeggings!\r\r(Photo: Frank Micelotta/PictureGroup)
Kanye West\r\r - There are few fashion limits for this rapper-turned-designer. In April 2011, ‘Yeezy was both praised and bashed when he rocked the Coachella Music Festival stage in a multicolored, silk long-sleeved shirt that went down the Celine Spring 2011 women’s runway.\r\r(Photo: Kevin Winter/Getty Images)Andre 3000 - He may have started his career in style synch with his OutKast partner Big Boi, but over the course of Benjamin Andre’s career he’s worn just about everything you can think of, and yes that has included platinum wigs, pink furs, fringe pants and the like. He could turn out any style you throw at him and make it work.(Photo: Kevin Winter/Getty Images)

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Ladies Only? - Nobody bats an eyelash these days when a woman has crossed over into menswear, but these male entertainers have made headlines for their foray into styles that were once considered “only for the ladies.” But, we have to admit, when it actually fits well and looks fly, we’re not mad at it! (Photo: Vince Bucci/PictureGroup)

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