This specific 'Black White' colorway goes with literally everything. However – the possible con? The comfort. If you're used to modern sneakers with Zoom or Boost, the "Jordan Air 1" will feel stiff. It's a flat, firm ride. Not for long days of walking, in my honest opinion. It's a style-first shoe, period. 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. So I finally got my hands on the Jordan Air 1 Mid 'White Gym Red'. At $130, it's a more accessible entry point. The build quality is solid — no major glue stains or anything. My honest take? It's a comfortable, everyday shoe. The mid-top gives a bit more ankle feel than the highs, but it's still that same legendary Jordan Air 1 profile. A great option if you're just starting your collection. In summary: The Jordan Air 1 is a 10/10 for style, a 6/10 for immediate comfort. It's a must-have for the culture, but a "know-what-you're-getting" purchase. Try them on if you can! See if that fit works for you. For me? They're forever in the rotation. What do you guys think? Let me know in the comments below!