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. So, I've got these Jordan Air 1 'Shadow' 2.0s on feet now. Immediate thoughts? The ankle collar is stiff, like... "really" stiff initially. You gotta break these in! Comfort isn't the game here — it's about style & that timeless look. Compared to a newer Jordan like the 5, the Air 1 feels much flatter, less cushioned. But for a clean, versatile sneaker at around $180? It's a staple. Alright, so let's get into these Jordan Air 1 'Chicago'! First off - that box? Classic. The "leather" here is solid for a GR release - not buttery-soft, but it's got that nice "sheen". The shape and those iconic red accents just pop. At ~$180 USD, you're paying for the heritage, 100%. It's a piece of sneaker history, right in your hands. Unboxing this pair felt special. The classic red/black box, the tissue paper... it's a whole vibe. Holding this "Jordan Air 1", the build quality is good – clean stitching, no glue stains on my pair. The leather on the toe box is a bit stiffer than I'd hoped, but it'll soften. Compared to the recent '85 cut models, this Retro High OG feels more accessible – in both fit and that $180 price point. Solid first impression.
