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. On foot — wow, instant thoughts. That jordan air 1 fit is snug, true to size. The support around the ankle is fantastic. Now, comfort-wise... it's a vintage basketball shoe. Don't expect modern foam clouds — it's firm! But, for daily wear / casual use? Honestly, I love that classic, grounded feel. The weight feels just right, not too heavy at all. Here’s the honest take: The biggest pro of the Jordan 1 is its legacy & style. It goes with everything. The con? That same classic build means it's not the most comfortable for all-day wear – the footbed is pretty flat. If you need arch support or plush cushioning, this isn't your shoe. It's for the look, not long-distance comfort. Major pro? The "versatility". This $210 sneaker goes with almost anything. Its cultural impact is huge - that's a big part of what you're buying. The build quality on my pair is consistent, no glue stains or major flaws. For a classic, it's hard to beat. It just "works" for so many different looks and occasions.