Era of Prominence: 1998-early 2000s

Before Jay-Z changed clothes there was this: a time when he wore jerseys. No sports team was off-limits. Hov's extensive collection included the Chicago Bulls, New Jersey Nets, Chicago Cubs, New York Jets, and Los Angeles Angels, amongst others. He wore jerseys in some of his most memorable videos and shows. Who could forget the New York Knicks jersey he wore in the "Izzo (H.O.V.A)" video? Or the one he wore at Hot 97's Summer Jam in 2001 when he brought Michael Jackson on stage? These days you're more likely to spot him in a custom Brooklyn Nets jersey.