It goes with almost anything. For $100-200+ USD in the "Jordan series", it's a worthy investment. But listen, if your priority is all-day, walk-all-over-comfort above all else? There are better modern options. The "AJ1" is about style + heritage first. Know what you're buying. Comparing it to other "Jordan" models? Well, if you want comfort, go for a "Jordan 3" or "13" with more Air units. The "Air Jordan 1" is about heritage & aesthetics, "first". The toebox creases easily – that's part of its character, but some folks hate that. For $180 USD, you're paying for the icon status. If you're new to the "Jordan" series, this is a "fantastic" starting point to understand the hype. Here we have the classic "nike air jordan 1" 'Chicago' – the grail for many. Unboxing this re-release is always special. The red-and-white color-blocking is just iconic. Putting them on, you feel the history... and also the firm sole. Let's be honest, the tech is old. For around $200+ USD, you're paying for the legacy. The pros are obvious: unmatched style and heritage. The con? It's not a "comfort-first" shoe. It's perfect for sneakerheads and style enthusiasts, but terrible for anyone prioritizing modern cushioning tech. So I copped this Air Jordan 1 Mid with the altered "Satin" swoosh. The presentation is cool! In hand, the materials are a mix – some standard leather, some interesting accents. On foot, it performs like any other Mid: good for the price (~$120 USD). The unique design elements are what you're paying for here. It's a fun twist for someone who already has a few core AJ1s and wants something different. As a first or only Jordan 1? I'd probably point you towards a more classic color-blocking for maximum versatility.