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! Alright, what's up, everyone? Just got these Jordan 1 Retro Highs in the 'Chicago' colorway in hand, and man… the box opening is still a "vibe". The iconic color blocking? Just pops. At around $180 USD, it’s a classic for a reason. Honestly, slipping them on… it’s the same familiar, slightly stiff feel that built the legacy. The cushioning isn't modern, but that's not the point. For pure style & history? These jordan air 1s are "unbeatable". They're perfect for collectors & casual wearers, but not for folks needing max comfort. In summary: The "Jordan Air 1" delivers exactly what it promises — a timeless look, great materials (on most colorways), & unbeatable versatility. The downsides? The firm ride & potential break-in time. For $180, it's a staple. If you love the design, you won't be disappointed. Just manage your comfort expectations & you'll have a shoe that lasts for years, both in build & in style. After wearing these Jordan 1s for a bit, the leather does break in nicely. The fit is true to size, good width. The grip is decent on dry surfaces. Is it worth the price? For this colorway and quality, yes – if you love the design. But at retail or slightly above; I wouldn't pay a massive resell premium for the basic tech inside.