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, what's up, everyone? Just got these Jordan 1 Retro Highs in the 'Chicago' colorway in hand, and man… the box opening is still a "vibe". The iconic color blocking? Just pops. At around $180 USD, it’s a classic for a reason. Honestly, slipping them on… it’s the same familiar, slightly stiff feel that built the legacy. The cushioning isn't modern, but that's not the point. For pure style & history? These jordan air 1s are "unbeatable". They're perfect for collectors & casual wearers, but not for folks needing max comfort. Here’s a real downside: that classic toe box creases... "fast". If you’re someone who hates that look, this might bug you. Also, the ankle collar can rub a bit at first until it breaks in. It’s not for folks seeking ultimate comfort or a pristine, uncreased look long-term. You have to embrace the wear. Who is this for? Honestly, for anyone building a sneaker collection – it's a must-have foundation piece. It's for the person who values iconic style over max cushioning. Who isn't it for? Pure comfort seekers or performance basketball players (obviously!). For $180 USD, you're paying for the legacy. If you want a piece of sneaker history you can wear daily, this "Jordan Air 1" is a no-brainer. Just manage your comfort expectations!