The Rapper: Lil Wayne
The Women's Clothing He Wore: During the MTV Video Music Awards in August 2011, Weezy performed while wearing a pair of extra tight cheetah pants. It was later revealed that they were actually women's jeggings.
How Ridiculous Did It Look? Very. Like, did he really need to wear a belt with those pants? It was pretty clear that they weren't going to go anywhere.
Photo Credit: New York Magazine