The "Air Jordan 1 Chicago" looks incredible in natural light. The leather quality is decent for a modern retro. Fit-wise, it’s snug—I went true to size. The "biggest advantage" is its versatility; it goes with almost anything. A downside? The outsole is flat and not great for wet surfaces. Compared to a Jordan 3 or 4, it’s less comfortable. My verdict? A must-have for style, but not for your gym session or a long walk. Comparing it to other Jordans? The "AJ1" is much stiffer than something like a Jordan 3 or 4 (which have more cushioning). It’s also heavier. But for pure, classic basketball silhouette appeal? The "Air Jordan 1 Chicago" is arguably at the top of the Jordan Brand hierarchy. It’s the blueprint. Who should maybe skip it? If your main priority is all-day, cloud-like comfort — this isn't your shoe. Also, if you're on a tight budget, the aftermarket prices for these are crazy. And if you hate seeing creases on your toes — you'll be stressed. Big pro? Versatility and legacy. You're wearing a piece of sneaker history. The materials on this retro are good for the $180 price point. The color blocking is perfection – it’s simply one of the most recognizable sneakers ever made. A true grail for many collectors.