Wearing them, you feel secure. However, that high cut isn't for everyone; it can rub if you have sensitive ankles. For $180+ in this colorway, you're investing in a legend. Ideal for those who want that classic, protected feel. Not ideal if you crave unrestricted movement. Putting these "Air Jordan 1 Highs" on... yeah, it's that familiar feeling. The ankle support is great, but let's be real – the comfort is "not" modern. It's a firm, flat ride. Compared to something like a Jordan 11 or even a newer Jordan 3, it's night and day. For me? The look outweighs the lack of cushioning, but if you prioritize comfort above all, this classic might not be your daily driver. The beauty of the "Air Jordan 1 High" is in its simplicity. No crazy tech, just great design. My feet feel "secure", not necessarily "cushioned." It's a trade-off. Compared to a Jordan 13? Totally different world. This is about looking good, not performance basketball anymore. So I finally got my hands on this pair... the Air Jordan 1 High in the 'Chicago' colorway. Unboxing it is a moment, I'm not gonna lie. The red just pops! On feet, you immediately feel that iconic, slightly elevated silhouette. The cushioning? It's firm... very 1985. Don't expect Boost or React here. The ankle support, however, is fantastic. It's a perfect shoe for style and basketball culture history, but as a all-day, everyday sneaker? There are definitely more comfortable options out there.