4. Chief Keef
Bringing raw Chicago style to the masses.
Based on his style and influence alone, Keef is easily top five. He made the already infamous "dreads and Trues" look bigger than Chicago, and many have followed his every fashion move since he came out—for better or worse. Undersized polos with the collar popped, the Moncler vest that he made pop, True Religion Jeans with gravity-defying sag, and tons of Gucci—he's helped define the particular style of his hometown.