On the one hand, the Reebok Shaq Attaq II wasn't the best-looking shoe, and was a hell of a departure from the original Pump-based model. On the other hand, it was light, low cut, and preceded the vaguely similarly cut (and beloved) Air Jordan XIV by half a decade. Also, Shaq had lows while Kobe was still in high school.
18. Reebok Shaq Attaq II Low