4. Fitted Caps

To be fair, the fitted baseball cap would make the Top 100 Trends list for every decade before (or after) the Aughts, but the classic accessory had plenty of shine during this new era. In the earlier part of the decade, multicolored pinwheels popped off to complement the popularity of throwbacks, and by decade's end, streetwear teams turned out enough fitteds to rival their MLB counterparts.

LEADERS OF THE PACK:
New Era, Starter, Supreme, 10.Deep, HUF