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. Who should get these? Honestly, anyone building a sneaker collection – the Jordan 1 is a cornerstone. Also, if you value style over supreme comfort. Who should skip it? If you're on your feet 12 hours a day and need cloud-like comfort, look at a different model. This is a fashion & culture staple, first and foremost. Let me know your thoughts—do you prefer the classic leather builds or the newer, more premium material variations on the Jordan Air 1? For me, the simplicity of the OG shapes is still unbeatable. It’s a piece of sneaker history you can wear every day. Just maybe, don’t plan a long city tour in them on day one Putting them on... okay. Let's be real: the "Jordan Air 1" is not a modern comfort shoe. The cushioning is firm—it's more about style and that ankle support. The fit is true to size for me, and the "Air" unit (while subtle) does its job for all-day wear. Don't expect Boost or Zoom Air softness here. It's a classic, sturdy feel, which I personally don't mind.