6. Mac Miller
It's true what they say, "If it ain't broke don't fix it." Mac Miller has long been a fan of streetwear, rocking brands like Diamond Supply Co., ONLY NY, and Rocksmith. What's impressive though is that even now, even with all his new-found success, not much has changed with his style. He still co-signs many of the same labels he did years ago. That's how you know he developed his own sense of style very early on.