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. Sliding these on... yeah, the fit is TTS for me. Initial comfort? Don't expect anything revolutionary – the Air Jordan 1 is famously firm underfoot. It's about support, not plushness. The ankle collar gives great lockdown, though. If you're coming from a modern runner or even an Air Jordan 4, the break-in period for this Jordan Air 1 might feel a bit... "stiff" at first. Walking around in these, you "feel" the history. The weight is good – not heavy at all. But again, the ride is firm, reminding you of its 80s roots. Compared to newer Jordan models with better tech, it's a trade-off: iconic look vs. modern comfort. For me, the look wins. This "jordan air 1" just makes a simple outfit look "considered". It's a statement piece, honestly. Who is this for? Honestly, for anyone building a sneaker collection – it's a must-have. Also great for style-focused wearers who value iconic design over tech. Who should skip it? Performance athletes or folks seeking ultimate comfort. This is a fashion & culture piece, first.