24. Lil Wayne
Height of Style: Tha Carter III
Signature Look: Dreads, full body tatts, ice grills, bright sneakers
His recent excesses with jeggings and Trukfit aside, Wayne has been a style leader for the better part of a decade. He's been commanding America's attention since his rebirth from Hot Boy prodigy, to being coined "the best rapper alive" after the release of Tha Carter III, to his current skater persona. Wayne has become a unique figure in pop culture and hip-hop and thus, generations of rap fans have looked up to his various personas. Even through his current stage of wild animal-print looks, he remains true to himself. Can't knock that.