1. Air Jordan XI "Black/Red" — Michael Jordan 

Year: 1996 

The Air Jordan XIs debuted during the 1995 NBA Playoffs when Michael made his comeback after the baseball strike and fell to Orlando in the second round. It didn't take long for Jordan and company to get back on top, though — the '96 Bulls set a league-record with 72 wins and skated through the post-season in their signature playoff black kicks. The "Concords" might be more iconic, but the black patent leather paired with the red Jumpman and sole made history. It's just different.