Year (of Sneaker): 2009
When: All-Star Game

Red All-Star sneakers will forever be associated with Mike's running mate, Scottie Pippen, but there's no reason MJ couldn't have joined in the fun. Too bad Jordans weren't made in too many different colors back in Mike's heyday. The red suede "Toro Bravo" Vs would have been crazy in 1990—or 2009.