15. Jermaine Dupri
JD took the whole slick producer/rapper schtick that Diddy popularized it and gave it a fresh ATL take. And hey if he managed to pull a chick like Janet Jackson, it's safe to say it worked. While he cleans up awesome in a suit or can stunt by rocking coordinating Louis Vuitton gear at a basketball game, he also takes style risks like Polo cricket sweater vests, matching shorts, red boat shoes, and a pork pie hat in the summer.