The solid rubber outsole, the sturdy build... these will last years. The creasing becomes part of the character. A potential downside for some? The high-top can feel restrictive if you're not used to it. But for ankle support and that iconic look, it's a worthy trade-off. Sliding my foot in… immediate thoughts? The fit is true to size, but the break-in period is real – that stiff, classic build means it’s snug at first. The jordan air 1 isn't known for "cloud-like" comfort, and that holds true. You buy this for the style, period, not for a plush ride. Sliding these on... immediate thoughts? The fit is true to size for me. The "Jordan Air 1"'s ankle collar offers solid support, & the overall wrap feels secure — not too tight, not loose. It's a structured shoe. The insole is pretty basic, though, so don't expect plush cushioning right away. It's more about that classic, grounded feel, which I actually kind of prefer for everyday wear. Final thoughts? I'm really happy with these. The "jordan air 1" delivers exactly what it promises: a timeless design that looks great. It's not trying to be something it's not. Just manage your expectations on comfort out of the box, and you'll have a staple in your rotation for years. Solid pickup.