35. Lupe Fiasco
Height of Style: 2008
Signature Look: Wire frames, varsity jackets, crewneck sweatshirts, Nike SB Dunks, Gucci accessories
Lupe was a continuation of unconventional style (for mainstream rappers) coming out of Chicago. While Kanye made it alright to dress in rugby shirts and other preppy classics, Lupe was one of the major reasons skater punk became acceptable to the next generation of hip-hoppers. Plus, he has had two clothing lines under his belt; Trilly & Truly and Righteous Kung-Fu. Most stylish rappers only have one. Since then he has collaborated with Vans and maintained an interest in new Japanese designers.