49. Snoop Dogg

Height of Style: MTV Video Music Awards, 1996 
Signature Looks: Dickies, Converse, button down, pimp suits

Snoop defined West Coast gangster cool post-Eazy E—even more than Pac, who pulled inspiration from everywhere—keeping it Crip and codifying the cholo-inspired Dickies, Chucks, and button-ups. He veered toward pimp mid-career and launched a line of custom products, from sneakers to Cadillacs, only to return to the gangster trope in the "Drop It Like It’s Hot" era. With a recent turn to Rasta, Snoop Dogg Lion has taken his weeded-out, laid-back style to its logical conclusion.