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. I've worn these 'Bred Toe' Jordan Air 1s all day. Here's my real take: they look incredible, but my feet are definitely feeling it. There's minimal impact protection — you're basically walking on the insole & a thin air unit. Compared to something like a Jordan 3? It's night & day in terms of cushioning. I'd recommend these for short outings & style, not for all-day comfort. Comparing it to my other Jordans... The Air 1 feels more substantial than an Air Force 1 (in my opinion) but less bulky than a Jordan 4. It’s that perfect middle ground. The price? Consistent with the legacy. You're buying into the Jordan series origin story every time you lace up a Jordan Air 1. Final verdict time. Pros: Timeless design, incredible versatility, true-to-size fit, and strong cultural cachet. Cons: Firm ride, toe creasing, and a premium price for a simple construction. The Jordan Air 1 is a legend for a reason – but it's a style/icon play, not a tech marvel. Know what you're getting into, and you'll likely love it.