
21. Air Jordan 18
The most noteworthy thing about this shoe is that it was the last of Jordan’s playing career. Heavily influenced by Italian sports cars and fashion, it even came with a towel, brush, and driver’s manual. You’ve got to love the production’s imagination even if the design itself seems a little low-key.

Designed by Wilson Smith, they actually look a bit like Kobe Bryant’s Adidas 1. Inspired by the sleek racing lines of the auto world, carbon fiber-based monocoque of F1 race cars, and race car driving shoes, there’s a lot going on. While it’s tasteful, it’s not dramatic enough to rank higher on this list.