17. Nike Air Huarache (1991)
These shoes are like a science experiment gone incredibly right. They combine the tight fit of a water-skiing bootie and a Mayan sandal to create one of the most comfortable shoes ever. Snug and cozy. And they look good too.
Like the Air Jordan 4 from a couple of years earlier, the Huarache’s incorporate plastic into the design. Reminder, this was not common in the early 90s. But the real coup here was the neoprene bootie. It was like a warm sleeping bag for your foot.