True to size for me. The leather needs some wears to soften up — that's the honest truth. Once it molds to your foot, the fit is great. The "advantage" is the lockdown; your foot isn't sliding around. But if you have wider feet, this might feel restrictive. For $180+, you're paying for the iconic Chicago配色, not for cutting-edge comfort. Manage those expectations. Final verdict? For me, the Air Jordan 1 Chicago is absolutely worth it. It's the blueprint. The comfort isn't mind-blowing, but that's not the point. The point is owning and wearing an icon. The build is good, the look is perfect. If you've ever wanted a pair, this is the one to get. Just manage your comfort expectations! In summary: The "Air Jordan 1 High OG "Chicago"" is a masterpiece of design. You buy it for the iconic look & cultural weight, not for tech. It’s perfect for collectors & style-focused wearers. Just know what you're getting into – a firm, classic basketball shoe that looks incredible. Worth every penny of that $180 USD to me. Okay, let's get this "Air Jordan 1 Chicago" box open. First impression? It's "perfect". The leather feels solid, the iconic silhouette is sharp, and that "Chicago" color blocking... it just "hits different". This is the definition of a "grail" for a reason. At $180 USD, it's a premium Jordan Series release, but for this specific colorway? Totally justified for collectors and purists.