The leather is good, not great. Also, if you have wide feet, go up half a size. The break-in period is real. But honestly, for the "Air Jordan 1 Chicago", you're paying for the legacy and the look. The pros "heavily" outweigh the cons for me. On feet now — and honestly, the "Air Jordan 1 Chicago" feels exactly how you'd expect: iconic, but not exactly plush. The ankle support is great, lockdown is solid, but the cushioning? It's firm. That's the classic AJ1 experience. If you're coming from something like a Jordan 13 or even a newer 5? It's a different world. You buy this for the look, not for cloud-like comfort. Let's be real: you buy the Air Jordan 1 Chicago for the look. The silhouette is arguably the most influential ever. On feet, they elevate any simple outfit instantly. As a piece of wearable history, it's unmatched in the Jordan series. The potential downside? They're everywhere now. The "hype" might be gone for some, making them less exclusive. But that also means you can actually wear them without fear—which is a pro in my book. Opening the box, the "Air Jordan 1 Chicago" just commands respect. The colorway is legendary—so crisp. Trying them on, the ankle support is great, but the forefoot is roomy in a classic way. They look even better on foot than in the box. Compared to a Dunk, they feel more substantial. At $180 USD, it's a fair price for this level of icon status. Pro? You own a piece of history. Con? They require some care—that white leather scuffs, the red can bleed. Perfect for the collector who wears their kicks, but maybe not the best "beater" shoe. A must-have, but with realistic expectations.