That stiff, break-in period is real – your feet might need a few wears to adjust. Also, at $180, you're paying for the legacy more than cutting-edge tech. If you want modern comfort, look elsewhere. This "Air Jordan 1" is about style & story, not a cloud-like feel. Who should maybe skip it? If your main priority is all-day, cloud-like comfort — this isn't your shoe. Also, if you're on a tight budget, the aftermarket prices for these are crazy. And if you hate seeing creases on your toes — you'll be stressed. On foot review: The "Air Jordan 1 Chicago" looks even better in motion. The way it creases — it's part of the charm. The advantage is its timeless design; it'll never go out of style. The potential drawback? That price tag — around $200 for a shoe with 1985 tech? You're paying for the legacy. If you want modern performance, this isn't it. But for style points? Unbeatable. Pros? It's the ultimate sneaker icon, period. The colorway is timeless & goes with literally "everything" - jeans, shorts, you name it. Durability is also a big plus; the materials on this OG High version are built to last through a lot of wear. It's a piece of history you can actually walk in.