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. Alright, let's get into this. Just unboxed the Nike Air Jordan 1 'Chicago'... and wow, man. That classic silhouette? It never gets old. For around $180, you're getting a piece of history in a box. The leather feels decent, the red just "pops", and the build quality is solid for a retro. A straight-up icon, no question. On-camera, this "University Blue" color "pops". It's a statement. Compared to more muted Jordans, this one demands attention. The leather is decent—not the best ever, but good for the price point (~$170 USD). The advantage? Instant outfit completer. The drawback? Lighter colors show creases & dirt faster. You gotta be ready to maintain them. Alright, let's get this "unboxed". First look at this Air Jordan 1 'Chicago'... "damn", that color-blocking is just iconic. The leather feels premium straight out the box. Slapping these on, the ankle support is insane, but that forefoot? A "bit" stiff, honestly. For $190, you're paying for the history & the style—not cloud-like comfort. If you want a piece of sneaker history that goes with "everything", this is it. If you need all-day cushion, look elsewhere.