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. Now, the potential downside? That flat, firm footbed I mentioned. If you're on your feet all day, it might not be the most comfortable option. Also, the leather can crease — some people hate that. I think it adds character, but it's worth noting. It's not a "performance" shoe by today's standards. Who should "avoid" it? Performance basketball players—this is not a modern hoop shoe. People with wide feet might find the fit snug. If all-day, cloud-like comfort is your #1 priority, there are better (but often less cool) options. The "Air Jordan 1" demands a slight comfort sacrifice for style. That's the trade-off. Alright, let's get these on foot. Initial feel? They're...stiff. Honestly, the Jordan Air 1 is "not" a comfort shoe out of the box. The ankle collar needs some break-in time, for sure. But that lockdown? It's fantastic once laced up. You feel secure, just don't expect Boost or React-type cushioning here. It's a different era of feel.