You can wear a pair from 5 years ago and it still looks current. The "con"? They can crease... a lot. Some love that "lived-in" look, some hate it. Using force fields helps, but it changes the fit. It's part of the deal with this model. Just something to know before you cop! Honest review time. The Jordan Air 1 is a lifestyle shoe, period. The cushioning is basic – you feel the ground. If you have wide feet, maybe go a half-size up for comfort. But man, that design... it's perfect. Compared to newer Jordan models, it's lighter and less technical. Perfect for collectors and casual wear. Not for runners or comfort-seekers. Bottom line from my review: the "jordan air 1" is a legend for a reason. It looks fantastic on-foot, pairs with everything, and represents a huge moment for the Jordan brand. Just go in knowing the feel is classic, not cloud-like. Would I recommend it? Yes - as a style cornerstone. But it's not trying to be something it's not, and I respect that. Final verdict? For me, it's a yes. The Jordan 1 High OG 'Chicago' is worth it. It's a cornerstone. The look, the history, the sheer versatility… it's unmatched. Just go in knowing the comfort is classic, not modern. As an all-time-great design? 10/10.