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. Let's talk pros & cons, straight up. "Pro": The "Jordan Air 1" is a legend. The cultural impact is undeniable, and this release nails the aesthetic. "Con": That classic build means a break-in period. The toe box might feel a bit rigid at first. If you prioritize plush comfort above all else, this might not be your daily driver. It's more for the style & the heritage, which, for many, is totally worth it. On foot now with these Jordan Air 1s. First thing you notice? The ankle collar and that classic fit. They're "snug" - a bit stiff out the box, honestly. It's not a plush, modern feel... it's that classic '85-'86 court feel (but for walking). If you need crazy cushion, look elsewhere. But for style? Unbeatable.