25. Rick Ross
Height of Style: "Aston Martin Music" video
Signature Look: Versace glasses, silk shirts, Christian Louboutin sneakers
The Boss is in the details. Ross is one of the more under-appreciated style pioneers who made his immaculate groomed beard a signature, and had a glistening chain made that immortalized that beard in diamonds. Ross went from being clowned about his fake designer shades to having one of the tightest sunglasses, sneaker, and silk shirt collections in the game. He might benefit from keeping his shirt on, but like everything else about Ross, he seems to have a gift of making the entirely unacceptable fly. Rozay himself put it best: "excess is just my character."