The security around the ankle is a game-changer for some. Versus newer Jordans? There’s no Zoom air here, no crazy tech. It’s simple, and for many, that’s the point. If you want modern performance, look at the ‘Jordan 37’. If you want timeless style, this ‘Jordan 1 High’ is your answer. So I'm lacing up the classic Air Jordan 1 High 'Chicago' (2022 version). The red just pops on camera, it's unreal. First impression? It's "the" blueprint. On foot, it's exactly what you expect: iconic, but not what I'd call comfortable for long walks. The pro is its timeless status in the Jordan series. The con is the price—resale is steep. If this is your grail, go for it. If you just want a comfortable red shoe? There are better, cheaper options. It's a heritage piece, first and foremost. Now, the con – and it's a big one for some people: comfort. If you're used to React foam or Boost, the firm midsole of the "air jordan 1 high" will feel like a brick. Seriously. Also, that high-top collar can rub against your ankle. It's not for everyone, especially if you prioritize all-day cushioning. Is it comfortable? It’s a "supportive" comfort, not a "squishy" one. The "Air Jordan 1 High" keeps your foot stable. After a few wears, the insole packs down a bit and it gets better. But if you have wide feet, that narrow toe box can be a real issue — consider going up a half-size. My genuine advice? Try it on first if you can.