Kanye West’s Nike Air Yeezy

In April of 2021, these Jordans were sold at a Sotheby's private sale. They are the most costly actual, wearable Jordans on this list. These Jordans are one of the most expensive Air Jordan sneakers of any kind, ever sold.

Kanye West wore a prototype of these Nike Air Yeezy 1s during his performance at the 2008 Grammy Awards. These prototype sneakers brought around $1.8 million.

That performance from 2008 has become a music awards legend. West performed "Stronger" in front of a neon pyramid, which opened to reveal Daft Punk dressed in red and white for the ceremony. They made their Grammy debut with a live remix of "Harder, Better, Faster, Stronger" alongside West.

Price: $1,800,000