Year released: 1986

Looking back now, the Air Jordan II is a classic. From its Italian construction to its lightweight polyurethane midsole to its clean Swooshless upper it was a shoe that was 100 percent ahead of its time. Which was a problem seeing that it needed to be a hit in 1987. Michael Jordan wound up wearing the original Air Jordan for two seasons rather than one, thanks in part to a broken foot that sidelined him for all but 18 games of his second season. When he came back and handed Larry Bird’s Celtics 63 points on their home floor in the 1986 NBA Playoffs, he did it in the Air Jordan 1. The Air Jordan II was a huge leap forward in terms of design and technology, but it was also over half again the price of the original ($100 from $65). There was a lot about the II that consumers—and maybe Jordan himself—weren’t ready for. When several of the execs who helped mastermind the Air Jordan line left Nike, Jordan nearly followed. Then Tinker Hatfield showed him what he had in mind for the Air Jordan III and the rest, as they say, is history.