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. After wearing these Jordan 1s for a bit, the leather does break in nicely. The fit is true to size, good width. The grip is decent on dry surfaces. Is it worth the price? For this colorway and quality, yes – if you love the design. But at retail or slightly above; I wouldn't pay a massive resell premium for the basic tech inside. Final take? The "jordan air 1" is a must-have for any well-rounded collection, period. It's the blueprint. But be honest with your needs. "Love": The timeless design, the outfit-elevating power, the heritage. "Note": The initially stiff feel & basic cushioning. I'd recommend it to collectors, style-focused folks, & Jordan enthusiasts. I'd "skip" it if technical, modern foot support is your #1 concern. Hope this honest review helps! Let’s talk pros & cons. Major pro? Iconic style & versatility. The "jordan air 1" is a legend for a reason. Con? The tech is "old". If you want modern cushioning, look elsewhere. This is about heritage, not performance innovation. It's a lifestyle piece, first and foremost.