Kanye West

Yeezy has a history of wearing skirts. He made headlines for the first time when he walked out during a Watch the Throne performance wearing a leather skirt. When it comes to fashion, Ye understands how to break down barriers and get people talking when he steps out in one.

Diddy

Mr. Profitable Another man who isn’t afraid to wear a skirt is Diddy. You can wear whatever you want when you’re as wealthy as he is. In 2010, while performing at MTV Crashes Glasgow, the business mogul wore a kilt.

Vin Diesel

Vin Diesel, as filthy and nasty as he is in The Fast and Furious, still knows how to work a skirt. In 2003, at the MTV Europe Music Awards, the muscular actor sported a leather skirt. He’s giving Kanye a run for his money, to put it mildly.

Andre 3000

Andre has always been known for his colorful and unusual style, so it’s no surprise that he’s not scared to wear a skirt. In UGK’s “International Players Anthem” video, the entertainer donned a skirt yet still managed to seem more manly than most.

Snoop Dog

In 2007, for the MTV Europe Music Awards, the OG of all West Coast rappers didn’t mind donning a skirt. Snoop looked dapper in his blue kilt, and he turned a lot of heads.