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! 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. So, who is this for? Honestly, it's for the first-time Jordan buyer, the collector who needs the cornerstone of the series, or just anyone who appreciates iconic style. The Jordan Air 1 is a must-have foundation piece. For $180-ish USD, you're paying for history and a design that changed the game. Comparing this to my other Jordans... the "jordan air 1" is "lighter" than a Jordan 3 or 4. The toebox has more room than newer models, which is great for wider feet. But remember, it's an '85-inspired cut—so it fits a bit longer. My advice? If you love basketball heritage and clean lines, this is for you. If you need cutting-edge tech, skip it.