The leather on most "Air Jordan 1 High" releases will crease, and fast. Some people hate that; I think it adds character. But if you're super particular about keeping your kicks pristine, this might stress you out. The pros still win for me: iconic status, incredible color-blocking options, and that unbeatable silhouette. For ~$190 USD, you're buying into a legend. 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. Alright, the Air Jordan 1 High 'Midnight Navy' is here. Classic color-blocking with a deep, rich navy—so versatile. The materials are decent for the $170 tag. My real talk? Every time I put on an AJ1 High, I'm reminded why it's iconic… and also why it's not for everyone. The flat, firm footbed is a stark contrast to something like a Yeezy 350. It's a style powerhouse and a must for any Jordan collection, but if you have wide feet? Proceed with caution, they run narrow. Comparing this to my other Jordans... the "Air Jordan 1 High" stands alone. It's not a performance shoe like later models. It's a fashion icon. The ankle padding is thick, which I like for support, but some find it restrictive. My verdict? If you want your first piece of sneaker history, or a pillar for your rotation, get it. If you need all-day comfort, look at Jordan 13s or something more modern.