5. Diplo

Diplo is an all-around musical technician. He's got house, dubstep, dancehall, Baltimore club, and even K-pop on lock. Don't think he does rap? Wrong. His new joint for Wale is tough. Just like his music, he also changes up his personal style by dressing down and dressing up in all kinds of sharp suits. Versatility is an important part of being stylish, so he gets major props from us.