Honestly, the comfort is decent – not modern-cushioning-level soft, but supportive. The break-in period is real, though. It’s snug, and you definitely feel that structured ankle collar. Compared to something like a Jordan 3, it’s much firmer. But, hey, that’s part of the classic Air Jordan 1 experience. If you need pillowy comfort, look elsewhere. Alright, so I just unboxed these "Air Jordan 1 Chicago" 85s, and the first thing? The "vibe" is insane. That classic red box, the tissue paper... it feels special. The leather on this 2022 version? Honestly, it's pretty good! Stiff at first, sure, but that classic silhouette is "everything". If you're a fan of the Jordan series history, this $180 investment is all about that iconic look. Who should skip it? If comfort is your #1 priority – maybe you're on your feet all day – this isn't your best bet. Also, if you prefer more muted, low-key shoes, the vibrant Chicago red might be too loud for your personal style. It's a statement piece, for sure. On camera, this shoe just pops. The "air jordan 1 chicago" colorway is literally designed for attention. Up close, the craftsmanship is solid for a general release. Wearing them, you feel that connection to basketball history—but yeah, the footbed is flat. At $180, it's an investment in a legend. I'd recommend it to any sneakerhead completing their "Jordan" series collection. For pure comfort seekers? It's a hard pass.