It works with "so" many styles. The con? That stiff leather and minimal cushioning need a "real" break-in period—your first few wears might be a bit... unforgiving. At ~$180, you're paying for the legacy, not cutting-edge tech. Alright, first impression out of the box—this "air jordan 1 high" feels... iconic, you know? The Chicago colorway is just stunning in hand. Checking the leather, it's decent—not the absolute best, but for the $180 price? It's solid. You can "literally" feel the history with this shoe, which is wild. Comparing this to newer "Jordan series" models — like the AJ4 — is night and day. The "AJ1 High" is about that raw, old-school basketball feel. There's no Zoom air unit, no fancy tech. It's simple, it's flat, and it's iconic. That's its biggest pro: it's a legend. The downside? Don't expect modern performance comfort. If you prioritize cushioning above all else, look elsewhere. But for a classic sneaker rotation staple, this is it. Comparing it to other Jordans? It's the foundation. A Jordan 1 high feels more structured and flat than, say, a Jordan 4 or 5. It's less about tech and more about style—which isn't a bad thing! It's like comparing a classic car to a modern one; both are cool, but for different reasons.