The toe box on these "Air Jordan 1"s will crease, and it'll happen fast. Some people hate that, but I think it adds character — it shows you wear your kicks! If you're someone who wants your sneakers to look pristine forever, this might stress you out. For me, it's part of the journey. The leather develops a story, which is kinda cool. Sliding these on... okay, immediate thoughts. The fit is true to size, and the ankle support is there. But let's be real - the "air jordan 1 retro high og" is "not" a modern comfort shoe. It's stiff, the cushioning is basic. You wear this for the look & the history, period. Compared to newer Jordan models? It's night and day in terms of tech. Still, that classic feel is part of the charm. Alright, let's get into these Air Jordan 1 Retro High OG 'Chicago's. First impression? The box, the red/white/black colorway—it's iconic for a reason. On foot, the ankle collar needs a bit of break-in, but the leather quality on this retro is solid. Compared to a modern Jordan, like a 36, the tech is obviously dated—it's a firm, flat ride. But that's the point. If you want history on your feet and a timeless look, this is it. If you need cushioning for all-day comfort, maybe look elsewhere. Wearing these 'Bred' Air Jordan 1 Retro High OGs out today. The upper is sturdy, offering decent support for all-day wear. Compared to a newer Jordan like the 5 or 13, the tech is basic—no Zoom air, just a simple sole. But that's not the point! The point is the iconic look & the versatility. Pros? Goes with everything. Cons? The insole is pretty basic. I'd recommend these to any sneakerhead starting their collection.