True to size for me. The leather needs some wears to soften up — that's the honest truth. Once it molds to your foot, the fit is great. The "advantage" is the lockdown; your foot isn't sliding around. But if you have wider feet, this might feel restrictive. For $180+, you're paying for the iconic Chicago配色, not for cutting-edge comfort. Manage those expectations. Who is the "Air Jordan 1 Chicago" for? Sneakerheads, obviously. It's for anyone who wants "the" most recognizable sneaker of all time. Who is it "not" for? People seeking modern comfort or those on a tight budget. For $180, you want performance? This ain't it. You want a legend in your closet? This is it. Honestly, holding this pair, you feel the weight of sneaker culture. The "air jordan 1 chicago" is arguably the most important colorway ever. Trying them on, the toe box has a nice shape, and the materials feel good. It's a simple shoe, but that's the beauty. For $180 USD, you're buying a piece of art. I'd say it's perfect for first-time AJ1 buyers or veterans. Not ideal for performance basketball, obviously—that's not its job. Putting them on — here’s the real talk. The Air Jordan 1 isn't known for crazy comfort, and yeah, that's true here. It's a firm, supportive feel. The ankle collar is high, offering good lockdown, but don't expect Boost or Zoom. For me, the classic look outweighs the, let's say, "vintage" cushioning. It’s a trade-off with this iconic Jordan series model, for sure.