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. Sizing tip time! For the Air Jordan 1 High, I always go true to size. They break in and mold to your foot. But here's my real opinion: this shoe is more about the "look" than the "feel". When you have them on, they complete an outfit like few other sneakers can. That high-top silhouette just works. Compared to a Jordan 3 or 4, it's slimmer and less bulky. Is it worth the hype and the $180? For a fashion piece and a cultural icon, yes. For a performance or all-day walking shoe, no. It's a legend, but it's not trying to be something it's not. Know what you're buying into. Now, the potential con: break-in time. That stiff leather can rub at the heel or pinky toe initially. It "does" get better, but the first few wears might be a bit... uncomfortable? Also, the flat traction is just okay on super slick surfaces. It's a casual/ lifestyle shoe first, remember that. Who should buy this? New sneakerheads starting a collection. Streetwear fans who value iconic style. Anyone who appreciates design history. It's a must-have piece. Who should skip it? People who prioritize cutting-edge comfort above all. If you need a squishy, bouncy ride, this classic nike air jordan 1 isn't for you.