42. Cory Matthews 

As Seen In: Boy Meets World
Notable Sneakers:
Air Jordan VIII, Air Jordan IX

Boy Meets World still holds up as one of the greatest things to go down on Friday night other than Book-It ('90s babies missed the golden era). But who knew all those years that while Cory was macking on Topenga he was rocking some serious heat along the way? Let's just hope the sequel competes with the original.