It goes with everything. The con? That same classic build means it's not the most comfortable for all-day wear – the footbed is pretty flat. If you need arch support or plush cushioning, this isn't your shoe. It's for the look, not long-distance comfort. Final verdict on this Jordan Air 1. As a sneaker reviewer, I own "many" pairs. This design never gets old. The $190 USD price tag is steep for the tech you get, but you're investing in a "legend". It's the shoe that started it all. Pros: unmatched legacy, versatile style, durable build. Cons: basic comfort, creasing leather. Perfect for any sneaker collection. Not ideal as your only walking shoe. Would I recommend it? For fans of style history, 100% yes. Comparing it to other Jordans? Big difference. My Jordan 3s or 4s are way more comfortable. The "jordan air 1" is the foundation, the blueprint. It's lighter than a lot of newer models, which is nice for all-day wear. But if you want that plush, sunk-in feel? Look at later models. This one’s for the history books and your closet. Sliding these on... yeah, the fit is TTS for me. Initial comfort? Don't expect anything revolutionary – the Air Jordan 1 is famously firm underfoot. It's about support, not plushness. The ankle collar gives great lockdown, though. If you're coming from a modern runner or even an Air Jordan 4, the break-in period for this Jordan Air 1 might feel a bit... "stiff" at first.