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. Walking around in them... yeah, you feel every bit of that 1985 DNA. The sole is firm, the ankle support is high – it's a very "grounded" feel. I love the elevated look it gives me, style-wise. But compared to a Jordan 3 or 4? It's less forgiving on the foot, for sure. That's the trade-off for that sleek, low-profile silhouette. If you prioritize looks – win. If you prioritize plush comfort – maybe look elsewhere. My final take? For around $220, it's a "solid investment into sneaker culture". It's not the most comfortable shoe in my collection, but it's one of the most worn. The "jordan air 1" delivers exactly what it promises: iconic style. If you don't have a pair, it's worth it. If you're on the fence, maybe wait for a colorway you truly love. Here’s a real downside: that classic toe box creases... "fast". If you’re someone who hates that look, this might bug you. Also, the ankle collar can rub a bit at first until it breaks in. It’s not for folks seeking ultimate comfort or a pristine, uncreased look long-term. You have to embrace the wear.
