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. Here's the latest pickup: the "Air Jordan 1 Retro" High '85 'Georgetown'. This is a more premium release, closer to $200. Unboxing it, you notice the higher cut and the slightly different shape—it's more faithful to the '85 original. The materials feel a step up. On feet, it's the same story: incredible presence, but a stiff, unforgiving ride. The padding is a bit thinner, so it feels more minimal. It's a shoe you wear for the statement, not for cloud-like comfort. Pro? Ultimate heritage style and superior construction. Con? The price and the dated feel underfoot. This is for the purist, the "Jordan" historian. For a casual wearer wanting comfort, it's a tough sell at this price. Just got this 'Stage Haze' pair in. The color blocking on this "air jordan 1 retro" is cleaner than I expected from pictures! Construction is decent. On-foot feel is... predictable. Secure, but you'll feel the floor. Compared to a modern basketball shoe? It's night and day. Pro: ultimate streetwear staple. Con: not for wide feet, honestly. At this Jordan series price point, you're buying the look. I'd recommend it for fashion-focused folks, not for comfort seekers. Final verdict? For the 'Chicago' colorway—worth it, even at resale (if you can swing it). It's "the" icon. For a general release pair? Absolutely a great purchase at retail. You're getting a legendary design that never goes out of style. Just don't expect it to feel like a modern runner.