Air Jordan 21

Another driving/car inspired Jordan, the Air Jordan 21 (Air Jordan XX1 or XXI) relied purely on quality materials and build to stand out from the rest. Higher-cut than most Jordans, the Air Jordan 21 took cues from the Bentley Continental GT (the grille was reflected in the front of the sole), and featured further luxury-inspired elements like a quilted lining. A red suede version (the more common colorways were done up in full-grain leather) looked like it could have come straight from Michael Schumacher’s closet. All models featured molded ankle areas with raised “23” branding. As if there could ever be any doubt whose shoes these were.

The simple yet elegant upper of the Air Jordan 21 (XX1) belied its high-tech underpinnings — much like its Bentley counterpart. The XX1 featured an updated version of IPS that included a replaceable column in the heel, allowing the wearer to select Zoom or regular Air cushioning (at least in that small area — an idea that would be realized more fully in later models). And finally the lace covers were a thing of the past. Instead, the Air Jordan 21 had a ventilated tongue that could be left open or closed depending on the wearer’s whim.

As Michael Jordan’s playing days receded further into the past, the Jordan Brand had to rely more and more on their active players, a disparate bunch that included not only young guns like Carmelo Anthony and All-Stars like Ray Allen and Jason Kidd, but vets like Juwan Howard and Richard Hamilton. The Jordan Brand roster showed off the versatility of the flagship shoe, but was no replacement for the best player ever when it came to marketing punch and that final note of authenticity. Which is probably why each new Air Jordan was heralded as being designed with Jordan himself in mind — and given both his legendary competitiveness and attention to detail, they undoubtedly were.