5. Wu-Tang Clan
Years Active: 1992-Present
Key Members: RZA, GZA, Method Man, Raekwon, Ghostface Killah, Inspectah Deck, U-God, Masta Killa, Ol' Dirty Bastard, Cappadonna
Elements of Style: Polo Ralph Lauren, Wu-Wear, Clarks Wallabees, Baggy jeans, 6-inch Wheat Timberlands
Wu-Tang ran the gamut of '90s street style staples. Whether it was Ghostface Killah's penchant for crepe-soled Clarks Wallabees, Method Man's bucket hat game, or The RZA's propensity for doo-rags and football jerseys. Nothing was fitted (except maybe the occasional baseball cap) either—it was baggy and awesome as hell. In 1994, they dropped Enter The 36 Chambers, but it was Hype Williams' video for "Can It All Be So Simple" that made Raekwon an instant style icon.
He was rocking the an anorak from Ralph Lauren's "Snow Beach" collection for Polo, and at the time, Lo-heads reigned supreme. People were literally getting stabbed for their jackets (yes really, we asked Just Blaze). 1995 saw the release of the Wu Wear clothing line, which was started by their manager at the time, Power. Much of the line capitalized on the crew's iconic "W" logo. Meanwhile, Ghostface Killah made a name for himself as the "wallabee champ," and his 1996 album art for Ironman features Raekwon and Cappadonna in front of a slew of custom Clarks, decked out in fresh Polo gear, natch.