15. Prep

Some say that a certain college dropout made it cool to look like an Ivy Leaguer, but even after 'Ye moved on, the preppy steez continued to get high marks throughout the decade. Ralph Lauren launched Rugby, J.Crew got their shit together, and prepping up became the smart move.

LEADERS OF THE PACK:
Jack Spade, Gant, Brooks Brothers, Rugby, J.Crew