The biggest one? The comfort—or lack thereof. If you're used to React foam or Air Max, the "Air Jordan 1"'s firm feel will be a shock. It's a lifestyle shoe now, but it reminds you of its 1985 roots. That said, the pros—like this unbeatable "Chicago" colorway—far outweigh that for me. It's a piece of history you can wear. Comparing them to my other Jordans is interesting. Vs. a Jordan 1 '85 cut? This retro has a slightly different shape. Vs. something like a Jordan 4 or 5? The "air jordan 1 chicago" is way less bulky and techy. It's all about that pure, old-school basketball look. The pro is its timeless style. The con? Don't expect any cushioning tech here. It's a flat, classic experience. Final thoughts? This shoe, the Air Jordan 1 Chicago, is legendary for a reason. The colorway is perfect. It's a must-have for any serious Jordan Series fan. At $180, it's an investment in sneaker culture. Not for comfort seekers, but for style purists and historians, it’s essential. My personal view: a timeless piece everyone should experience once. Who is this for? Sneakerheads, collectors, anyone who loves classic style. The Air Jordan 1 Chicago is a must-have for any serious rotation. Who isn't it for? Folks seeking all-day comfort or cutting-edge tech. It's a flat, firm shoe. But for pure, undiluted sneaker culture? This is arguably the peak.