
20. Air Jordan XVII
These were the first $200 Air Jordans, definitely a landmark at the time. Furthermore, they came in a metal briefcase with a CD-ROM, which has kind of aged badly. However, they gain points because Jordan actually wore them while with the Washington Wizards in 2001-02.

But they definitely do look better than some of the shoes that came after them over the next few years. Not all Jordans have aged well as fashion items, even if they retain the collector’s value. These were high-performance shoes with a TPU heel stabilizer and a full-length shank plate.