Some might find the leather a bit flat compared to premium remakes. The insole is basic. For $180, you're buying the legend, not hyper-luxury materials. The ankle collar can rub a bit initially. If you're after the absolute best leather quality in a Jordan 1, you might wait for a special release. But, this is the accessible OG. Who should maybe skip it? If your main priority is modern comfort & performance tech for all-day wear or sports... look at newer Jordan models. Also, if you're on a tight budget and $180 feels steep for a "basic" leather shoe, I get it. The value here is in the heritage, not the groundbreaking features. Just being honest! Let's talk "real" wear. The "Air Jordan 1 Chicago" is a style "powerhouse"--jeans, shorts, it elevates everything. However, that beautiful white leather scuffs easily, so if you're rough on kicks, be warned. For $180, you're buying a piece of history. Worth it for style enthusiasts? 100%. For performance or worry-free beaters? Maybe look at other Jordan Series models. Putting them side-by-side with my other Jordans—the Chicago colorway just dominates the shelf. The color blocking is perfect. On foot, they feel secure and stable, though the sole is firm. A major plus is the timelessness; you can wear these in 10 years and they'll still look fire. A potential downside is the price—resell can be crazy. But for retail? It's an instant cop. This is the definition of a classic in the Jordan series.