Year: 1998
Sneaker: Air Jordan XIV

Imagine trying to tell Michael Jordan not to wear a certain shoe after he's already gotten it. For that matter, imagine trying to tell Michael Jordan not to do anything. He'd worn the Air Jordan XIII through much of the regular season and the playoffs, but once the Finals rolled around, he needed something even more special. Black low-cut XIIIs made an appearance, but even that wasn't enough. So he unveiled that next-next shit, the Ferrari-inspired Air Jordan XIV. Now that's how you leak something.