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. On foot now, and the fit is true to size for me. The break-in period is real with these, especially around the heel and ankle collar - it can be stiff at first. The cushioning? It's not plush like some modern sneakers, but that's the classic Air 1 feel. You get that solid, grounded sensation, which I actually prefer for all-day wear. Honestly, my first thought unboxing this $180 "jordan air 1" was, "The toebox creases are gonna show fast." And they will—that's part of the charm, though. Sliding them on, the fit is narrow initially but molds to your foot. The high-top design offers good stability for casual wear. The benefit is the iconic, never-goes-out-of-style design. The drawback is the lack of modern cushioning. I'd say these are perfect for fashion-focused folks, but not ideal if you're seeking a plush, "forget-you're-wearing-them" kind of shoe. On feet, visually? The Jordan Air 1 just works. That high-top profile gives a killer, confident look with jeans or joggers. In the Jordan series, it's the blueprint. Compared to a Jordan 11 or a 4, it's less bulky and way more versatile for everyday wear. The main "pro" here is its timeless style. The "con"? Don't expect performance basketball tech.