21. Air Jordan 5 (1990)
This shoe had it all. 3M tongues, asymmetrical collars, translucent outsoles, and visible Air Units. This shoe was a juggernaut and literally, everyone had to have a pair. If you were a kid when these came out the most incredible thing was the visible air cushion.
You had seen the commercials touting the technology but now you could actually see it. And if your friends looked real close when you jumped they could actually see the air cushion at work. At that moment you were the coolest kid on the block.