It’s no secret hip-hop culture is known for making and breaking trends. A sartorial swing that’s become pretty acceptable, or not, is rappers in dresses.

READ: Young Thug and His Dresses

Yes, men are wearing dresses and sometimes kilts as well. Of course, not every man can pull off this look, and it does take a certain amount of confidence to wear this particular article of women’s clothing.

From vets like Diddy and Kanye to newcomers such as Jaden Smith and Young Thug here’s the best of men who rock the mic and a hot dress!


Young Thug

Young Thug is a fascinating character and not just because of the way he raps. The Cash Money signee is very open about wearing dresses. So open, he can be seen wearing a sheer dress in his cover shoot for Dazed magazine.


Kanye West

Throughout 2011’s ‘Watch the Throne’ tour, Kanye West could be seen wearing a kilt on stage as he performed alongside Jay Z. So why did Kanye wear the kilt? In an essay for Paper magazine, he said it was him “paying his dues “ to the fashion world. “I paid my dues when I had to wear a kilt in Chicago, and friends would say, ‘What’s your boy got on?’ There are warriors that have killed people in kilts in the past. Who gets to decide what’s hard and what’s not hard?”



In 2010, while performing in Glasgow, Scotland, Diddy wanted to immerse himself in the culture, and wore a kilt while performing on stage along with a jacket, vest, black hat, calf-high boots and sunglasses. It’s number 40 on Complex’s list of ‘Worst Hip-Hop Fashion Fails of All Time.”



 Jaden Smith

Jaden Smith marches to the beat of his own drum from the way he thinks, makes music and his style choices. He wore a dress to prom with actress Amandla Stenberg, and it worked!


Cee-lo Green

Cee-lo Green has his own style of not only music, but fashion as well. You never know what you’ll see him wearing at an event. It could be a sequined feathered jumpsuit or a long dress you see women on the Mother’s Board at church wearing. Either way, his style choices keep us talking!

Brittney Fennell

Brittney Fennell

Brittney is the Associate Editor of Jawbreaker and a writer who has goals to disrupt culture in ways unseen.