That stiff, break-in period is real – your feet might need a few wears to adjust. Also, at $180, you're paying for the legacy more than cutting-edge tech. If you want modern comfort, look elsewhere. This "Air Jordan 1" is about style & story, not a cloud-like feel. 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. Initial impression: The box, the tissue paper—it's an "experience". The "Chicago" 1s look even better in person. The leather has a nice sheen. On foot, they're snug (I went TTS) and the toe box will soften. Styling? Unmatched. They're the centerpiece of any fit. A key advantage is durability—these aren't flimsy. A possible downside? The high-top can feel restrictive if you're used to lows. It's a $180 USD purchase that's more about "emotion" and style than cutting-edge performance. Ideal for enthusiasts; casual buyers might not "get" the hype. Alright, so the moment I opened the box, man... that classic ""Chicago"" colorway just hits different. The "Air Jordan 1 Chicago"'s red is so vibrant against the white and black. The leather on this 2022 version feels "solid"—not super plush, but it has a nice, classic grain. Holding it in hand, you just feel the history of the whole "Jordan series". Honestly, for around $180, the presentation alone is a win.