The downsides? The firm ride & potential break-in time. For $180, it's a staple. If you love the design, you won't be disappointed. Just manage your comfort expectations & you'll have a shoe that lasts for years, both in build & in style. Got the classic 'Chicago' Jordan Air 1 Retro High OG. Man, unboxing this legend... the red just "pops" against the white. It's history in a box. On foot, it's the same familiar fit—secure, but don't expect cloud-like comfort. It's about the look and the legacy, "period". Comparing it to newer Jordan models with Zoom? No contest on cushion. Pro: unbeatable iconic status. Con: premium price (often over $200) for a "firm" experience. A grail for collectors, but a practical choice for daily beaters? Maybe not. Let's be real about the cons. The main one? That flat, firm midsole. If you're on your feet all day, this isn't your go-to "comfort" shoe – you'd want something with more tech. Also, the toe box creases... it's gonna happen, it's part of the leather's charm (or annoyance, depending on your view). So, this specific Jordan Air 1 model isn't for the comfort-first crowd. Check out this pair: the Jordan 1 Craft 'Inside Out'. The concept is cool—you see the raw foam edges, flipped Swoosh. In hand, the deconstruction feels premium. On foot, comfort is similar to a standard High, but the look is what you're paying for ($150 USD). It’s a conversation starter. Pro? Unique take on a classic. Con? Not for the traditionalist. If you have a few OG jordan air 1s and want something different, this is great. If it's your first Jordan 1? Maybe start with a classic colorway.