3. Theophilus London
This Brooklyn rapper has one of the best personal styles, period. He doesn't bow down to rules and has the ability to mix different styles. Catch him in velvet slippers one day and Jordans the next. While he's known for his vintage finds, he also rocks Givenchy tees and velvet Balmain pants. Even brands and designer take notice of his unique look and are eager to work with him. In fact, he's collaborated with Cole Haan and Del Toro, and more recently, Stussy.