11. P. Diddy
Height of Style: 2007 Ninth Annual "White Party"
Signature Look: White Suit
Sean Combs is one of the style gods of hip-hop, without question, and the arguably the producer-rapper-mogul with the most fashion accomplishments to his name. His Sean John label was the first hip-hop line to get high-fashion props—a Council of Fashion Designers of America nomination for "Menswear Designer of the Year" in 2000—and his colognes are best sellers. He's also known for his "white parties" where the Ciroc flows aplenty. Plus, he has a bad chick like Cassie next to him. It's pretty clear who's (still) winning at life.