14. Air Jordan V – $10,000
First released in early 1990, this fifth edition of the Air Jordan came up with new translucent rubber soles. Unfortunately, people complained about them causing the shoes to have slippery nature as they collect dust.
The designer, Tinker Hatfield, meant no harm, of course. He was inspired by the fighter planes used during the World War II. The inspiration can be seen on the shark teeth shaped mid-sole.
This particular Air Jordan V is the special edition produced in 1990. There were only a few of them released. They were custom made for Michael himself. The shoes bore his legendary jersey number, 23, on the sides.
Despite the slippery issue, the unique design, the number 23, and Michael Jordan’s autograph give enough reason to make it worth $10,000 for just one single pair.