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. On foot now, and the fit is true to size for me. The break-in period is real with these, especially around the heel and ankle collar - it can be stiff at first. The cushioning? It's not plush like some modern sneakers, but that's the classic Air 1 feel. You get that solid, grounded sensation, which I actually prefer for all-day wear. Alright, on-foot first impressions: The comfort is... classic. Don't expect modern foam, you know? It's a firmer ride—that's just the Air 1 DNA. The ankle collar locks you in nicely, though. For walking around, style > squishy comfort. If you want plush, look elsewhere. But for that timeless look? It delivers, every time. My final take? At around $170-$200 for most retros, the value is in the design. You're buying into a legend. For a first Jordan? It's a perfect start. For a veteran? It's a necessary classic. Just go in knowing the feel is classic, not cloud-like. Would I recommend it? Absolutely – but with those caveats.
