Year: 2001

Back in the late '90s and early 2000s, a closet wasn't complete unless it had at least a couple of "way too big" throwback jerseys in it, and few collection's rivaled Hov's. A throwback Julius Erving Sixers jersey paired with a white Roc Nation T-shirt tied around his head, a Latrell Spreewell Knicks jersey standing next to Michael Jackson on the Summer Jam stage in 2001, or a Jets jersey with the green fitted to match were just some of the fits in his repertoire at the time. But this particular fit worn by Jay-Z to perform "Izzo" at the 2001 MTV VMAs is among the best. He took the stage outside of the Metroplitan Opera House in New York City rocking a white Michael Jordan Bulls jersey, baggy denim shorts, and a pair of "Fire Red" Air Jordan Vs. Almost two decades later, the jersey choice was a nice bit of foreshadowing. Both men are widely considered the GOATs of their respective crafts. —Mike DeStefano