3. Snoop Dogg
Snoop Dogg, or Lion, hasn't made a great song in a while, but we still have faith in the Doggystyle emcee. Every once and a while he comes from left field, and a cloud of smoke, and drops a gem on the rap world. However, his style needs some getting together. He dresses like your eccentric family friend who grabs anything in his closet. Back in the day, he had one of the freshest styles, but as of late, he wears sandals with socks, red furs with track pants, and boot-cut jeans.
Snoop, we know you have some cash. Get yourself a stylist, please; it will do wonders for your image and might even spawn another summertime classic.