They do get more comfortable! The leather softens up, molding to your foot. Is it worth the ~$180 USD? For a sneakerhead wanting a classic, yes. For someone seeking a performance running shoe feel? Absolutely not. It's all about understanding what you're buying here. Who's this for? Sneakerheads who love the heritage, or anyone wanting a style staple. If you need a shoe for all-day walking? Maybe "not" your first pick. The support is good, but the cushioning is basic. For "$180+", you're paying for the iconic Jordan series name and that unbeatable silhouette. It's a wardrobe piece. Sliding these on... yeah, you feel the history. The ankle collar gives great support, a signature of the "Jordan ʕ•́ᴥ•̀ʔっ" series. Compared to, say, a Jordan 11? It's much stiffer. The advantage is durability and that crisp look. Disadvantage? It's not for performance basketball or all-day walking, in my honest opinion. Opening the box, the shape of this "air jordan 1 retro" is perfect – no toe box weirdness. This 'Stage Haze' pair has a great mix of materials. Wearing them, the high-top feels supportive, not restrictive. The major advantage is its place in sneaker history – it's an icon. The possible deal-breaker? The price (approx. $180) for a shoe with 1985 tech. Worth it for design, not for tech.