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The Best Air Jordans Are The Ones You’ve Overlooked

Ben Affleck’s Air (out now in theaters) is a sports movie with nearly no sports being played. With one of his stronger directorial efforts to date (not coincidentally, he keeps his acting on the sidelines), Affleck has found a subgenre many of us didn’t know we needed: This is a sports marketing movie. 

Air centers around the marketeers behind a then-new icon: Michael Jordan. Specifically, it tells the real-life story of Nike executive Sonny Vaccaro (a slightly pudgy, intensely focused Matt Damon) who in 1984 signed then-rookie Michael Jordan to a $2 million deal launching a basketball shoe that would redefine how we think about the game and its footwear, Nike, and Jordan himself, forever: the Air Jordan.

The Air Jordan was a game changer out of the gate—quite literally, as the initial red-and-black shoe Jordan wore on the court in 1985 violated NBA rules with its flagrant coloring (Nike paid the penalty fees, as the movie shows). Since then, the Air Jordan has had its many ups and downs, and looks almost quaint in today’s vast, competitive sneaker landscape. But there’s no question that sneaker culture as we know it, so pervasive in chatter among sneakerhead obsessives, can be traced back to that first iteration.

“We wouldn’t be talking about the history of basketball shoes if it hadn’t been for Air Jordan,” says Simon Rasmussen, a New York-based stylist who has dressed Pharrell and Dennis Rodman, among others.

The Air Jordan I is still the most coveted among collectors. Given near-universal critical acclaim for Air, and Affleck’s general shooting percentage, we might be poised for another cultural surge around the mythos of the 1.

“For me personally, it’s the 1s and 11s that are the most stylish and fashion-relevant,” Rasmussen says. “Basketball shoes you could show up to at a party or any event and not be asked to leave.” The 1s, he notes, are “magical” in part due to “the simple silhouette, and they look the least like a basketball shoe that we know today.” Meanwhile, the 11s are praised for their patent leather and a wide array of color configurations. 

But absolutely do not overlook the Air Jordan 2 line, according to experts. Hitting retail shelves in 1986, the Air Jordan 2 was intentionally designed (with Jordan’s input) as both a significant upgrade to and departure from the original. The Nike Swoosh was suddenly nowhere to be seen, in favor of simply the Jordan Wings logo. And at $100 a pop in the mid-’80s, these were staggeringly expensive sneakers—a sign of things to come.

Courtesy of StockX & Tyler Schoeber

While they still don’t get the most love, the Air Jordan 2 was “technically a huge upgrade over the Air Jordan 1 in terms of a pure basketball shoe,” according to B. Pagels-Minor, founder of DVRGNT Ventures and a bona fide sneakerhead who has amassed a collection of over 125 sneakers, including several of the most sought-after on the market.

Though visually understated, the Air Jordan 2, with its cushy leather upper for support (including faux-iguana skin manufactured in Italy!), truly ushered in the modern “luxury” sneaker, “cementing the Jordans as the fanciest basketball shoe,” Pagels-Minor says. It doesn’t hurt that the 2 was also a pioneer in “consistently appealing to women through women’s sizing.”

Yet the Air Jordan 2 was perhaps fated to be underrated coming on the heels of the legendary “Jumpman” drop (so named for its iconic logo featuring a silhouette of Jordan shooting). “They tried elevating the sneaker by having no external branding, and I think that doomed its success,” says writer and stylist Nic Screws, who’s dressed stars on screen like Rami Malek and on the court with Russell Westbrook. “But Jordan broke a lot of records while playing in the Air Jordan 2, and I think that’s what registers with true collectors now. Plus it’s more rare. It’s a flex.”

The innovative Air Jordan 11, too, while an object of fascination in the fashion community, has numerous releases with their own niche appeal.

If you must have the prized (and pricey) Air Jordan 1, go forth. For the true sneakerheads, the Air Jordan 2 and 11 releases are what discerning collectors recommend if you want to stand out from the masses—and not break the bank.

Stadium Goods
Best stone-cold classic

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For Rasmussen, it’s never a bad idea to go back to the classic red, black, and white colorway that became inextricably linked to Jordan himself. It’s also a style readily available on reseller websites like GOAT, Grailed, eBay, Stadium Goods, and Flight Club, where the stylist got a pair of 11s over 15 years ago. “I paid $500, which at the time was a bit crazy, but I couldn’t live without them!”

best designer collab

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The essential Air Jordan 2s come down to the designer collaborations, according to Pagels-Minor, who owns a pair released with Off-White, the late designer Virgil Abloh’s beloved label. But Pagels-Minor also recommends the Just Don x Air Jordan 2, J. Balvin x Air Jordan 2, and Union x Air Jordan 2 releases (see the grail below!). “Until recently, I think most people would have said the Air Jordan 2 was forgettable, but recent collabs have reenergized the line.”


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“I’ve always had a little fondness for the 11 because it’s less flashy than a lot of the other Jordan styles,” says Max Berlinger, style writer and New York Times contributor. And hey, you can never go wrong with grey.


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Some sneakers were meant to announce themselves. So goes this bold but never garish Air Jordan 2 collaboration with Union in Los Angeles, which Screws says are the 2 she would buy. “I like all the futuristic elements to this design, like the deconstructed tongue with exposed foam,” she says. “Plus the color pop of the bright blue.”

The Best Air Jordans are the ones you’ve overlooked

Starting at $157.00

“The Air Jordan 11 seems poised for a comeback,” Berlinger says. “It has a wavy, blobby vibe that reminds me of all the weird shoes coming out of luxury brands like Bottega Veneta and Givenchy. There was a pair of navy blue suede ones recently that I thought were pretty cool,” Berlinger says of the velvety Midnight Navy release, the first-ever women’s-exclusive colorway of the Air Jordan 11.