19. Air Jordan XVI "Cherrywood"
Year Released: 2001
2001 was a tough year for the signature Jordan line, but that means opportunity for underrated sneakers. Michael Jordan was in retirement and the retro of sneakers like the Air Jordan III meant that a lot of sneakerheads scooped up True Blues and Mochas in favor of the signature Air Jordan of the year. The "Cherrywood" version with the grey cover and white patent material is still slept on to this day.