Also, if you prefer low-tops or more understated shoes, this bold, high-top silhouette might not be your vibe. It’s a loud shoe in terms of heritage, even if the colors are technically simple. Biggest pro? The versatility and the legacy. This colorway is the most famous for a reason. It’s a sneaker you can wear for decades and it’ll always be cool. The materials on this release are generally good — nice, smooth leather that should crease in a classic way. It’s a piece of sneaker history you can actually walk in. So, final verdict? If you can get it for retail or a decent resale price, I say go for it. Holding this shoe, you feel the heritage of the entire "Jordan series". It's not the comfiest, but the look, the history, the sheer versatility... it's a 10/10 for me. A must-have, honestly. 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.