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. Here's my real talk on the "Jordan Air 1". Love the look, always will. But the "comfort"... it's "flat". Compared to even a basic AJ3, there's less cushion underfoot. It's a trade-off: iconic silhouette for modern comfort. For short wears or style shots? Perfect. For all-day concrete pounding? Your feet might ask for a break. Just being honest! 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. Here's a "Jordan 1" you don't see every day: the "Zoom Air CMFT" version. The "first" thing you feel is the "insole" – it's "way" more cushioned than a standard AJ1! The upper uses more stretchy materials too. It's a "modern twist" on the classic. The "huge benefit" is, of course, the comfort – you can actually walk in these all day. The "compromise"? It "doesn't" have the exact same stiff, structured look of the OG. If you've always loved the "Air Jordan 1" style but hated the feel, "this" is your shoe. Traditionalists might find it "too" different.