Height of Style: "Going Back to Cali" video
Signature Look: Red Kangol Bucket Hat, gold rope chain, boom box

LL seemed to understand the art of branding from the very beginning. His red Kangol, if not completely original, became his trademark—along with his "don't fuck with me" muscles. James Todd Smith's penchant for signature headgear—from Kangols to visors—became the subject of much speculation. As hip-hop grew up, so did he, going from endorsing brands like TROOP and FUBU to landing spots in Gap ads and smartening up in sharply-tailored suits. His Hollywood A-list status was recently confirmed when he hosted the Grammys last year.