Year: 1988
Sneaker: Nike Air Jordan III "Black/Cement"
Player(s): Michael Jordan

This is how you debut a shoe. First, you wear the white version while defending your Slam Dunk title in front of your hometown fans in the most hotly contested dunk contest ever. Then, the next day you sport the black version while dropping a game-high 40 (in 29 minutes) en route to MVP honors. Nobody did it better than MJ.