But if you want a piece of history that elevates your fit every single time, the "Air Jordan 1 High" is still a must-consider. Try them on if you can, know what you're getting into comfort-wise, and if the style speaks to you – you really can't go wrong. It's a legend for a reason. 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. Final verdict. I love my "air jordan 1 high", no question. It's a pillar of the "Jordan series". Would I recommend it? Yes — but with context. If you want a comfortable, tech-driven sneaker, pass. If you appreciate iconic design, history, and a shoe that completes outfits, this is for you. The $180 price tag is steep for the tech you get, but fair for the cultural weight it carries. It's not for everyone, and that's okay. For me, it's a forever classic. 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.