The leather softens up. For casual wear, running errands, even a casual office fit, they're great. You're not buying these for basketball or long walks. You're buying the "Air Jordan 1 Mid" for its unbeatable, iconic style and heritage. Putting these on for a full day… the break-in period is real, folks! That leather needs some time to soften up around the toebox. Once it does, the fit is secure and snug. I appreciate the Mid’s height – it offers a bit more support than a low-top, but less bulk than the High. A great middle ground, honestly. 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. On foot now... The fit is pretty true to size for me. It's a comfortable shoe, but let's be real -- it's not a modern performance sneaker. The cushioning is "fine", it's that familiar, slightly firm feel. The ankle collar gives good support though. If you're looking for cloud-like comfort, maybe look at a React or Zoom model. But for style? This Air Jordan 1 Mid is a timeless look.