Launch Gallery

When the world’s most famous sneaker debuted in 1985, it was met not with celebration but censure. The dramatic red-and-black Air Jordan I crossed swords with the NBA’s uniform police, who banned the shoe from the league for its “non-regulation” colors. Michael Jordan, then a Chicago Bulls rookie, bucked league brass by wearing his signature kicks, a decision which cost him $5,000 in fines every time he set foot on the court. You can’t put a price on fashion. Or winning.

Since its launch, the Air Jordan has become a global sports and style phenomenon, unquestionably the most famous icon of one of the world’s most famous brands. Every year since 1985, even after Jordan retired for good, a new pair of Air Jordans has been released, along with a countless number of colorways and models. In honor of the legendary sneaker, we asked a preeminent sneaker collector and Nike expert from Austin, Texas to rank the top 23 Air Jordans of all time. See our complete, illustrated feature in the photo gallery (at right, close CAPTIONS to see rankings).

Our ranking features Playmates Jessica Burciaga, Candice Cassidy, Francesca Frigo, Jaime Edmondson, Patrice Hollis, Hiromi Oshima, Kimberly Phillips, Tiffany Taylor and Heather Rae Young, posing in classic pin-up style. Cyber Club members get the uncensored illustrated version with 46 wallpaper-size images. See where your favorite sneakers and Playmates land on our list, and find out which epic Air Jordan comes out as Michael always did—number one.

Rankings courtesy Matt Halfhill, www.nicekicks.com

Photos by Jared Ryder; illustrations by Nigel Evan Dennis