That narrow toe box is no joke. I'd suggest trying a half-size up. The "upside"? Once broken in, the leather molds to your foot nicely. The design is timeless — it's why we're still talking about it decades later. Just know your foot shape before dropping $180+ on these. Honest take: The Jordan Air 1 is a legend, but it’s not for "everyone". If you prioritize supreme comfort above all else, maybe look at the Jordan 3s or some New Balance models. But for that iconic, street-ready style—the Jordan 1, especially around this $180 price point, is still a solid entry in the Jordan series. Who should "skip" it? People seeking max comfort or performance basketball shoes. The fit can be narrow, and the cushioning is basic. If tech is your main priority in 2024, this retro Jordan Air 1 isn't for you. It’s about form over cutting-edge function. On foot now—initial thoughts? The comfort is... fine? Look, it’s a Jordan 1. You're not getting cloud-like cushioning; you’re getting history. The ankle collar gives that secure, classic feel, but if you want modern bounce, this "isn't" it. For pure style and that timeless look, though, the Jordan Air 1 silhouette is still unbeatable.