The Rapper: Lil Wayne
The Women's Clothing He Wore: Wayne deserves two spots on this list. And that's because Jay Z isn't the first rapper to wear a women's sports jersey. In April 2011, Wayne wore a Skylar Diggins' jersey to support the women's basketball player.
How Ridiculous Did It Look? Pretty ridiculous, but it wasn't because of the jersey. What was up with those "shorts" and—ugh!—those socks?
Photo Credit: Black Sports Online