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)

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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)

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)

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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)

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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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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)

Pharrell\r - Pharrell said he spent the price of a high-end Mercedes on his huge, purple crock Hermes tote he posed with on the cover of Paper magazine, and he swears it’s not a murse. “It’s not a man purse. It’s my travel bag,” Pharrell said. Whatever you want to call it, we know the Hermès bag is a highly coveted staple for the ladies and his collection is probably keeping a few fashionistas on the wait lists.\r\r(Photo: Paper Mag)

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Pharrell\r - Pharrell said he spent the price of a high-end Mercedes on his huge, purple crock Hermes tote he posed with on the cover of Paper magazine, and he swears it’s not a murse. “It’s not a man purse. It’s my travel bag,” Pharrell said. Whatever you want to call it, we know the Hermès bag is a highly coveted staple for the ladies and his collection is probably keeping a few fashionistas on the wait lists.\r\r(Photo: Paper Mag)

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Prince - Is there any man who looks hotter in sparkles, ruffles purple or platform heels than Prince? We think not. Ladies have always considered this man a heartthrob, even if they did find themselves wanting his feminine clothes for their own wardrobe. (Photo: Kevin Winter/Getty Images)

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Prince - Is there any man who looks hotter in sparkles, ruffles purple or platform heels than Prince? We think not. Ladies have always considered this man a heartthrob, even if they did find themselves wanting his feminine clothes for their own wardrobe. (Photo: Kevin Winter/Getty Images)

Rick James\r\r - He was Rick James, b—ch. And yes his beaded extension braids and long curls were stunting on a lot of ladies in the ‘70s. If you look back through his flashy, body-hugging animal print and sequined outfits, you’d definitely find more than a few pieces that a woman could wear to be on trend today. We’d also wear some of his over-the-knee boots. \r\r(Photo: Glenn A. Baker/Redferns/Getty Images)

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Rick James\r\r - He was Rick James, b—ch. And yes his beaded extension braids and long curls were stunting on a lot of ladies in the ‘70s. If you look back through his flashy, body-hugging animal print and sequined outfits, you’d definitely find more than a few pieces that a woman could wear to be on trend today. We’d also wear some of his over-the-knee boots. \r\r(Photo: Glenn A. Baker/Redferns/Getty Images)

Cee Lo\r\r - Cee Lo hit the 2011 BET Awards dressed up as Patti LaBelle for the diva’s tribute in a big, crazy wig and sparkling jacket, but the look wasn’t too far off from his typical attire stunts. The rapper who judges the singing competition The Voice ended the show in a spiky-shouldered, red dress costume.  \r\r(Photo: Kevin Winter/Getty Images)

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Cee Lo\r\r - Cee Lo hit the 2011 BET Awards dressed up as Patti LaBelle for the diva’s tribute in a big, crazy wig and sparkling jacket, but the look wasn’t too far off from his typical attire stunts. The rapper who judges the singing competition The Voice ended the show in a spiky-shouldered, red dress costume.  \r\r(Photo: Kevin Winter/Getty Images)

Derek J\r - Audiences have watched Atlanta stylist Derek J kick up his heels on Good Hair, The Real Housewives of Atlanta and now at the judging table of Oxygen’s fantasy hair competition Hair Spectacular. It’s rare to see him without a pair of stilettos, leg-bearing mini shorts or a women’s accessory and "it bag." \r\r(Photo: Kyle Petrozza/PictureGroup)

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Derek J\r - Audiences have watched Atlanta stylist Derek J kick up his heels on Good Hair, The Real Housewives of Atlanta and now at the judging table of Oxygen’s fantasy hair competition Hair Spectacular. It’s rare to see him without a pair of stilettos, leg-bearing mini shorts or a women’s accessory and "it bag." \r\r(Photo: Kyle Petrozza/PictureGroup)

Lenny Kravitz\r\r - Lenny Kravitz paid tribute to the “American Woman” in his music and his street style often gives subtle nod to the clothes she may wear. Like any true rocker, he has an affinity for tight leather pants, but he’s also been known to layer on boas, purses and wedge heels. We especially think it’s cute that his daughter Zoe admitted he’s borrowed her T-shirts before. A tight shirt is all the better to show off those sexy muscles!\r\r(Photo: Reuters)

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Lenny Kravitz\r\r - Lenny Kravitz paid tribute to the “American Woman” in his music and his street style often gives subtle nod to the clothes she may wear. Like any true rocker, he has an affinity for tight leather pants, but he’s also been known to layer on boas, purses and wedge heels. We especially think it’s cute that his daughter Zoe admitted he’s borrowed her T-shirts before. A tight shirt is all the better to show off those sexy muscles!\r\r(Photo: Reuters)

What's Next?\r\r - Male entertainers have long worn earrings (some diamonds the size of broaches!) and chains, but over the past two decades especially, there’s been more and more who have rocked items that were once considered “only for the ladies.” Cam'ron helped rappers feel OK with wearing pink in the ‘90s and somewhere along the way in the ‘10s we’ve seen the rise of skinny jeans and deep V-necks. Some are even scooping up items straight from the women’s section. What women’s trends do you think will be the next to crossover?\r\r(Photo: Frank Micelotta/Getty Images)

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What's Next?\r\r - Male entertainers have long worn earrings (some diamonds the size of broaches!) and chains, but over the past two decades especially, there’s been more and more who have rocked items that were once considered “only for the ladies.” Cam'ron helped rappers feel OK with wearing pink in the ‘90s and somewhere along the way in the ‘10s we’ve seen the rise of skinny jeans and deep V-necks. Some are even scooping up items straight from the women’s section. What women’s trends do you think will be the next to crossover?\r\r(Photo: Frank Micelotta/Getty Images)