If you prioritize max comfort above all else, maybe look elsewhere. For everyone else, especially in the US where this colorway means so much, it's a legendary pickup. No hype, just facts. In summary: Stiff at first, but you break it in. Not super comfy, but unbelievably stylish. For $180 USD, you get a legendary piece. The "Air Jordan 1 Chicago" isn't perfect, but it's essential. That’s my real, honest opinion. What do you guys think? In summary: The "Air Jordan 1 High OG "Chicago"" is a masterpiece of design. You buy it for the iconic look & cultural weight, not for tech. It’s perfect for collectors & style-focused wearers. Just know what you're getting into – a firm, classic basketball shoe that looks incredible. Worth every penny of that $180 USD to me. First thing on foot? "Honestly?" It's a classic AJ1 feel. The cushioning is firm, not super plush like newer models. But that's part of its charm! The "air jordan 1 chicago" offers great ankle support & a snug, secure fit. It's not a "comfort-first" shoe, but for style & court heritage? Unmatched. You feel connected to the ground.