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. Just copped this newer Jordan Air 1 'Mid' version in 'Wolf Grey'. At a lower price point (~$115), expectations are different. The materials are more synthetic, but the shape is still there! On foot, they feel... fine. It's a budget-friendly way to get the iconic look. If you're a purist about materials & OG highs, skip it. But for a beater pair? Not bad at all. For my wide-foot friends, listen up: the Jordan Air 1 can be tricky. 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. Putting them on... okay. Let's be real: the "Jordan Air 1" is not a modern comfort shoe. The cushioning is firm—it's more about style and that ankle support. The fit is true to size for me, and the "Air" unit (while subtle) does its job for all-day wear. Don't expect Boost or Zoom Air softness here. It's a classic, sturdy feel, which I personally don't mind.