23. Air Jordan Retro XI "Cool Grey"
Original Release: 2001
Theoretically, an all-grey sneaker should be an absolute snoozefest. Good thing the people at Jordan don't pay attention to theories. The "Cool Grey" Air Jordan Retro XI was an immediate smash, and set off a whole slew of "Cool Grey" and "Wolf Grey" Air Jordan iterations. Not to mention the contrasting greys on the upper actually looked amazing.