The Rapper: Diddy
The Women's Clothing He Wore: During a concert in Scotland back in September 2010, Diddy put on a kilt for his entire set.
How Ridiculous Did It Look? This wouldn't have looked so strange if Diddy hadn't tried to make it look so damn cool. Additionally, other rappers like Kanye West and Kid Cudi beat him to the punch by wearing kilts first. So he looked ridiculous simply because he jumped on a trend that other artists had already tried to pull off.
Photo Credit: Huffington Post