Diggy Simmons

Celebrity Parent(s): Joseph "Rev. Run" Simmons

Yes, even though he's grown out from under the shadow of his father, Diggy still fits in on this list. We've peeped this dude's sense of style a while back when he first popped up on Run's House. Now, with newfound fame in the music industry, including a deal with Atlantic Records, Diggy's style has only gotten better. The only thing left to wonder is when will his clothing line drop.