10. Young Jeezy
The Thug Motivational speaker transitions between dressed-up and casual looks nicely, mostly thanks to a subdued color palette and luxe materials like embossed leather jackets and wool zip sweaters with leather piping. When he needs to clean up, Jeezy does it extremely well, pulling off midnight blue tuxedos with the best of them. That isn't to say his street cred is at stake—he'll still rock rugged denim looks and backwards snapbacks with appropriate matte black shades—no stunner shades for this classy dude.