That narrow toe box is no joke. I'd suggest trying a half-size up. The "upside"? Once broken in, the leather molds to your foot nicely. The design is timeless — it's why we're still talking about it decades later. Just know your foot shape before dropping $180+ on these. Alright, what's up, everyone? Just got these Jordan 1 Retro Highs in the 'Chicago' colorway in hand, and man… the box opening is still a "vibe". The iconic color blocking? Just pops. At around $180 USD, it’s a classic for a reason. Honestly, slipping them on… it’s the same familiar, slightly stiff feel that built the legacy. The cushioning isn't modern, but that's not the point. For pure style & history? These jordan air 1s are "unbeatable". They're perfect for collectors & casual wearers, but not for folks needing max comfort. Sliding these on... immediate thoughts? The fit is true to size for me. The "Jordan Air 1"'s ankle collar offers solid support, & the overall wrap feels secure — not too tight, not loose. It's a structured shoe. The insole is pretty basic, though, so don't expect plush cushioning right away. It's more about that classic, grounded feel, which I actually kind of prefer for everyday wear. Major pro? The "versatility". This $210 sneaker goes with almost anything. Its cultural impact is huge - that's a big part of what you're buying. The build quality on my pair is consistent, no glue stains or major flaws. For a classic, it's hard to beat. It just "works" for so many different looks and occasions.