Also, if you're super sensitive to a stiff break-in period, this might frustrate you. There are more comfortable "lifestyle" shoes out there for the same price, for sure. Final verdict? For me, it's a yes. 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. Major pro? Timelessness. This jordan air 1 design will "never" go out of style. It's a wardrobe staple. The construction feels durable, and it's surprisingly easy to style. The high-top offers good ankle support for casual wear. It’s just a reliable, iconic shoe. Not everyone will vibe with it, though. If your priority is cutting-edge comfort or max cushioning for all-day wear, look elsewhere. This isn't that shoe. Also, for some, the $190+ price for a "basic" leather shoe might feel steep. You're paying for the icon status. So, think about what you "really" want from a sneaker before copping this Jordan Air 1.