This "Chicago Black Toe" look is fire, and at around $125 USD, it's way more accessible than an OG High. The leather quality is okay—it creases easily, which I don't mind. Compared to other Jordans, like a Jordan 4, these are much lighter and less bulky. Pro: Iconic style that goes with everything. Con: The flat outsole isn't great for wet surfaces. Recommended for collectors and casual wearers alike. First lace-up… The "Air Jordan 1 Mid" provides that classic, supportive feel around your foot. It’s not a sloppy fit at all. The outsole grip is decent on dry surfaces. Where it might disappoint? If you have wider feet—it can feel narrow in the toe box. My advice? Maybe go half a size up if you're unsure. For the average foot, true to size works. It’s a straightforward, no-frills wearing experience, which I kinda respect. Sliding my foot into this "Air Jordan 1 Mid" 'Black Gym Red', the fit is true-to-size but "snug". The leather is stiff initially – no way around it. The flat footbed is the biggest thing to note; it's not a "comfort" shoe out of the box. But man, on foot, the profile is so sharp. It's a shoe that makes an outfit. Ideal for sneakerheads who appreciate the history. I'd steer clear if you have wide feet or need a lot of cushioning. On feet, this 'Chicago' "Air Jordan 1 Mid" looks amazing. The red really pops! Compared to the OG High version, the "Mid" lacks some of that top-tier ankle support, but honestly? For casual wear, it’s totally fine. A huge pro is the easier on-and-off. A con? That break-in period can be a bit stiff.