The Air Jordan 1 Hi ’85 “Chicago” Revival: Why 2026 Might Be the Year Sneakerheads Lose Their Minds

Let me take you back to a moment that’s etched in my sneaker-loving brain. It was 2018, and I was standing in line at 5 AM outside a boutique in Brooklyn, clutching a coffee that wasn’t nearly strong enough, surrounded by other bleary-eyed sneakerheads. We were all there for one thing: a chance at the Air Jordan 1 “Chicago.” I didn’t get them. Neither did the guy behind me who’d driven in from Pennsylvania. We both laughed about it later, but man, that sting stayed with me.

So when I heard whispers that the Air Jordan 1 Hi ’85 “Chicago” might be making a comeback in 2026, I almost spilled my morning coffee all over my keyboard. And trust me, I’ve learned my lesson about drinking near electronics!

The Return of the King

Word on the street is that Jordan Brand is planning something special for their 40th anniversary celebration. The iconic Air Jordan 1 Hi ’85 “Chicago” is possibly dropping in Fall 2025, and sneaker Twitter is already losing its collective mind. Can you blame them? We’re talking about arguably the most important basketball shoe ever made.

If you’re new to the sneaker game (or if you’ve been living under a rock), the “Chicago” colorway is THE Jordan colorway. White, red, and black – the colors Michael Jordan wore when he was changing the game forever with the Chicago Bulls. There’s something almost magical about how these three simple colors come together on this silhouette.

What Makes the ’85 Version Special?

Here’s where things get interesting. The ’85 version isn’t just any old retro. It’s Jordan Brand’s attempt to recreate the original 1985 model as faithfully as possible. That means a higher cut than the retros we’ve become used to, slightly different proportions, and materials that try to capture that mid-80s feel.

I remember when they released the first ’85 cut a few years back. My buddy Jake, who’s been collecting since the 90s, held them next to his worn-to-death original pair and got all misty-eyed. “It’s like seeing an old friend,” he said. I teased him mercilessly about it, but secretly, I totally got it.

The ’85 version feels substantial in hand. The leather has that perfect stiffness that promises to age beautifully with wear. The higher ankle collar hugs your foot in a way that modern basketball shoes just don’t anymore. It’s a time machine disguised as a sneaker.

The Price of History

Now, let’s talk money. These beauties are expected to retail for around $250, which ain’t cheap. But considering what original pairs go for these days (I’ve seen beat-up pairs sell for thousands), it’s actually not bad for what you’re getting.

Will they be hard to get? Is water wet? Is the sky blue? Do I spend too much time staring at shoes online instead of doing my taxes? The answer to all of these is a resounding yes. Nike and select Jordan retailers will carry them, but expect the usual madness: online raffles, camping out, the whole nine yards.

Why This Release Matters

I’ve seen countless sneaker “moments” come and go over my years collecting. Some live up to the hype; others fizzle out faster than my attempts at New Year’s resolutions. But this one feels different.

The Jordan 1 “Chicago” isn’t just another colorway; it’s the colorway that started it all. There’s something almost mythical about it now. Kids who weren’t even born when Michael was playing can recognize this shoe instantly. That’s not just marketing – that’s cultural impact.

I still remember seeing them on the feet of skaters in the 90s, on rappers in the 2000s, and on literally everyone from Wall Street guys to high school kids in the 2010s. Each generation discovers this shoe and makes it their own.

The Waiting Game

So now we wait. And plan. And maybe start putting aside a little cash each month (at least that’s what I’ll be telling my wife I’m doing).

If you’re new to this whole sneaker thing, here’s my advice: start building those relationships with your local sneaker shops now. Follow the right accounts. Maybe practice your online checkout speed. And whatever you do, don’t get your heart set on just one pair – that’s the fastest road to disappointment in this game.

In the meantime, I’ll be here, staring at my current rotation, telling my worn-out Jordan 1s to hang in there just a little longer. Their older brother might be coming home soon.

Who else is already planning their strategy for these? Drop a comment below – I’d love to hear if you’re as unreasonably excited as I am!