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. On foot now with these Jordan Air 1s. First thing you notice? The ankle collar and that classic fit. They're "snug" - a bit stiff out the box, honestly. It's not a plush, modern feel... it's that classic '85-'86 court feel (but for walking). If you need crazy cushion, look elsewhere. But for style? Unbeatable. Who is this for? Honestly, for anyone building a sneaker collection – it's a must-have. Also great for style-focused wearers who value iconic design over tech. Who should skip it? Performance athletes or folks seeking ultimate comfort. This is a fashion & culture piece, first. Hey what's up everyone, just got this new pair of Jordan Air 1 'Chicago' in hand. First thing you notice? That iconic silhouette is "clean". The leather feels pretty decent for this $180 price point, nothing crazy premium but solid. Unboxing it, you just "know" you're holding a piece of history. It's the classic that started it all.