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. Honest review time. The "Air Jordan 1 Retro" is a legend, but it's not for everyone. My pair here feels well-made, no glue issues. When I walk, the lack of arch support is noticeable if you're used to modern sneakers. The pro? Unmatched style points and durability. The con? It's not a "comfort-first" shoe. It's a fashion and culture icon. If you want a piece of sneaker history you can wear, go for it. If your priority is all-day comfort tech, maybe skip this one. Let's talk durability: the "Air Jordan 1 Retro" is a tank. The toe box creases, sure, but it adds character. The outsole rubber is thick and should last forever with casual use. Compared to newer "Jordan" models with more tech, like the 34 or 36, these are about style and history, not performance. That's not a bad thing – it's just what they are. Alright, let's get into these! "Unboxing" this Air Jordan 1 Retro 'Chicago' ($190) is always special. The leather feels decent, not premium but solid for the price. That classic silhouette? Timeless. On foot, they're a bit stiff initially, like most AJ1s. The ankle support is fantastic, but don't expect cloud-like comfort. It's more about the iconic look & style history. A must for collectors, but casual wearers might find them too unforgiving.