I went true-to-size, and the length is perfect. The width is "snug", not tight. For some with wider feet, this could be an issue—consider sizing up half. The ankle support is fantastic for a lifestyle shoe. Stepping out, you feel "connected" to the ground. It's not a squishy, modern sneaker. You buy the Jordan Air 1 for its legendary look and cultural weight, period. It's a wardrobe essential, not a comfort innovator. Guys, the Shadow Grey colorway of the "Jordan Air 1" is a "sleeper hit". In hand, the materials feel premium. On foot? They go with literally everything - jeans, joggers, shorts. The grey overlays break up the monochrome look perfectly. Compared to a louder Jordan 4, these are your "daily drivers". A definite win for a versatile rotation. So, my final verdict? If you want a piece of history and a style chameleon, grab the jordan air 1. If your priority is all-day comfort or performance basketball, spend your money on a newer model. For me, it's a keeper – flaws and all. It's just that iconic. Final verdict? For me, it's a yes. The Jordan 1 High OG 'Chicago' is worth it. It's a cornerstone. The look, the history, the sheer versatility… it's unmatched. Just go in knowing the comfort is classic, not modern. As an all-time-great design? 10/10.