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. Got the classic 'Chicago' Jordan Air 1 Retro High OG. Man, unboxing this legend... the red just "pops" against the white. It's history in a box. On foot, it's the same familiar fit—secure, but don't expect cloud-like comfort. It's about the look and the legacy, "period". Comparing it to newer Jordan models with Zoom? No contest on cushion. Pro: unbeatable iconic status. Con: premium price (often over $200) for a "firm" experience. A grail for collectors, but a practical choice for daily beaters? Maybe not. Looking at the Jordan Air 1 High OG 'Bloodline'. Unboxing, the black/red trim on white gives serious 'Chicago' vibes, but with a "twist". The red stitch detailing is a cool touch. Fit is standard—a bit narrow for me initially. The advantage here is the classic look with subtle unique details. Disadvantage? Like most OGs, it's not a comfort shoe. At around $170, it sits in the middle. I'd recommend these Air 1s to someone who wants an OG-style pair without paying resell for an actual 'Chicago'. Potential con? The "tech is dated". If you're used to React or Zoom, the "jordan air 1" will feel flat. The leather can also crease pretty noticeably - some hate that, I think it adds character. Also, breathability isn't great. It’s not a performance shoe, so manage those expectations, folks. It's a lifestyle piece through and through.