Jordan Geller, CC BY-SA 4.0, via Wikimedia Commons

And so we begin with the Air Jordan 1 in the Chicago colorway, in all of its 1985, game-worn glory. I must admit, I created this blog with the intention to bring light to cool shoes a non-sneakerhead might never have seen, but I couldn’t bring myself to write even a single entry before talking about these bad boys. These kicks are so incredibly classic that they almost represent Jordan Brand better than the Jumpman logo itself. The vibrant, candy-apple red upper contrasted against the cream midsole and night black swoosh make the sneaker pop in a way no successive shoe has been able to replicate.

Part of the magic of this shoe is the era in which it was made. Before the 1s, there were no sneakerheads—sure, there were standout pairs from the early days (namely Converse’s Chuck Taylor) but no shoe stood in as the image behind a cultural reset like the Air Jordan 1 High had. I still find it hard to believe that these shoes came out two decades before I was born, yet how they are still lauded by many (myself included) as one of the best-looking pairs of all time.

Although I could geek out about this shoe for hours on end, I want to talk about this shoe holistically, which means there are a few downsides to acknowledge. First, they are anything but cheap. The shoe resale market has exploded in the past few years, with companies like StockX being valued at $3.8 billion. Because of this rise in popularity, more and more people now view sneakers as collectibles rather than pieces of functional apparel; as a result, sneakers with the most publicity, or “hype” behind them tend to increase in value over time. Consequentially, with this pair being one of the most hyped on the market, they have skyrocketed in value. The kicks retailed for a modest $64.99 in 1985 (~$168 adjusted for inflation). Thirty-five years later, in a 2020 Sotheby’s auction, they fetched a jaw-dropping $15,120, and even the person who sold that pair should’ve waited a year—in 2021, fewer people offloaded their prized pairs, leading prices to rise even more—the only two sales on StockX in 2021 were for $19,000 and $20,000 each.

The only other negative when it comes to this shoe is comfort. Although I don’t own the 1985 Chicagos, Nike, seeing the popularity of this model, has repurposed, or “Retroed” the shoe throughout the years in a whole host of colorways. I was lucky enough to score a pair of the Jordan 1 High “Shadow” when they were released in 2018 (not—I paid more than double the pair’s retail price on the aftermarket) and still wear the shoe today. Although the plush upper fits like a glove around the ankle, the midsole leaves much to be desired. Although they’re fine as a lifestyle sneaker, I certainly can’t imagine playing basketball in them—as a matter of fact, neither could Jordan himself! In the 2020 documentary The Last Dance, Jordan recalled the time he played his last game in Madison Square Garden in 1998, sporting the Chicago 1s for old time’s sake. To quote Jordan: “By halftime my feet are bleeding. But I’m having a good game—I don’t wanna take ’em off” (Episode V, The Last Dance, 14:12). Okay, so maybe Michael could withstand the pain, but you get the idea.

Don’t let my criticism fool you, however. For every bad thing I have to say about this pair, I can think of a million positives. One of the most iconic shoes of all time, period.

Verdict: Fawn over. Gawk. Drool. Worth the $15,000+ price tag? To those that have millions of dollars of disposable income, go for it. Do I have that kind of money to drop on a pair of sneakers? In my dreams. 10/10 would recommend to any eccentric billionaire.