17. The Notorious B.I.G.
Height of Style: "Hypnotize" video
Signature Look: Coogi sweaters, double jesus pieces, custom white suits and fedoras, apple jack hats
Biggie's Puffy-assisted evolution from ice-grilling in Tims and bubble vests to the seductive dapper don he became just prior to his untimely death was a study in hip-hop alchemy. COOGI sweaters were just loud enough for this legend. Everything he wore helped define the '90s sartorial lexicon. His leather jackets and Versace shades maintained his street credibility, but when he rocked Groovy Lou's custom white suit, he evoked old blues and jazz musicians of a bygone era. Ashy to classy indeed.