If you have very wide feet, the narrow fit can be "truly" uncomfortable. This shoe demands a bit of a sacrifice for the sake of style. Be honest with your needs. Sliding these Air Jordan 1 Highs on, the fit is true to size for me. The break-in period is real, folks – they're stiff at first! The ankle support is top-tier, though. I feel locked in. Compared to something like a Jordan 3? Way less cushioning, no doubt. It's that classic, firm basketball court feel. Not for long walks, but perfect for style. 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. Speaking of style — this shoe "photographs" incredibly well. The crisp white, black, and red panels on the "Air Jordan 1 High" create such a clean look on-camera. In person, it's even better. The build quality feels consistent. A major pro? Its insane versatility. You can wear this with almost anything.