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. After wearing these Jordan 1s for a bit, the leather does break in nicely. The fit is true to size, good width. The grip is decent on dry surfaces. Is it worth the price? For this colorway and quality, yes – if you love the design. But at retail or slightly above; I wouldn't pay a massive resell premium for the basic tech inside. Final verdict? I'd recommend this "Jordan Air 1" to anyone building a sneaker collection, or someone who values style over supreme comfort. It's a must-have silhouette. However, I'd "not" recommend it to someone seeking a "comfort-first" daily driver, or for actual basketball. Know what you're getting: a legend, not a cloud. Alright, so let's get into these Jordan Air 1 'Chicago'! First off - that box? Classic. The "leather" here is solid for a GR release - not buttery-soft, but it's got that nice "sheen". The shape and those iconic red accents just pop. At ~$180 USD, you're paying for the heritage, 100%. It's a piece of sneaker history, right in your hands.