8. Cee Lo Green
Although he's come a long way from his Goodie Mob days, this rapper-turned-crooner remains a very stylish heavy-hitter. From studded red jackets to crocodile tracksuits and shiny hoodies, Cee-Lo isn't afraid to dress boldly. But even better, he knows how to tone things down, also being spotted in gear from streetwear brands like Crooks & Castles.