First wear? The insole is basic, but the overall construction feels solid. They look even better on foot than in the box, in my opinion. If you compare it to an Air Force 1, the AJ1 Low is noticeably lighter and less bulky. The advantage here is pure, simple style. The disadvantage? That classic feel means classic, minimal cushioning. For around $100 USD, it's a fair deal for a legend. Ideal for someone building a versatile sneaker rotation. Not ideal for long standing sessions, to be honest. Finally, the "Chicago" "Air Jordan 1 Low". The heritage is undeniable. Putting them on gives you that iconic vibe without the height of the OG. The leather is stiff at first but will mold to your foot. Is it worth it? For a classic colorway at a lower price point than the Highs... "absolutely". It's perfect for collectors and casual fans alike. Just don't expect cloud-like comfort. Who should "maybe" skip it? Hardcore comfort seekers, or people needing arch support. Also, if you're after the most "authentic" Jordan 1 experience, some purists will always argue for the High top version. The Air Jordan 1 Low is a lifestyle shoe first, performance second (or let's be real, not at all). On foot, the "Air Jordan 1 Low" just "works". The silhouette is iconic & low-key versatile. I'm wearing the 'Shadow' colorway ("~$120"), & it goes with literally "everything" - jeans, shorts, you name it. The low-top design makes it less bulky than the "Air Jordan 1" High, which I personally prefer for summer. On camera, the details pop - that Swoosh, the wing logo... it's a timeless look, "no" doubt.