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 review: day two. They're breaking in a bit! The comfort improves slightly as the materials loosen. I still love putting them on. The "Jordan Air 1"'s biggest strength is its "versatility". Dress it up, dress it down. The high-top provides decent ankle "presence" without being restrictive. If you're on the fence, and style > max comfort is your priority, I'd say go for it. It's a cornerstone sneaker. Sliding these on... okay, let's be real – the Jordan 1 is not a modern comfort shoe. It's a bit stiff initially, but the ankle support & lockdown are fantastic. It's that classic, supportive feel. If you're used to Air Max or React cushioning, the Air 1 will feel firm. But for style & that true retro basketball silhouette? It delivers. Conversely, who should "skip" it? If you have serious foot issues, need arch support, or are buying sneakers purely for athletic performance or all-day walking comfort—this isn’t it. Look at the React or Zoom lines instead. The Jordan Air 1 prioritizes form... over function, in the modern sense.