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. Now, the potential downside— and I have to be real with you— is the comfort tech, or lack thereof. If you need modern, bouncy cushioning for all-day wear or long periods on your feet, the "Jordan 1" platform might leave you wanting more. It's a firm, stable base, not a cloud. For some people, that’s a dealbreaker, and I totally get it. Who should probably skip it? Hardcore performance basketball players (obviously) or folks who only buy sneakers based on advanced cushioning tech. 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. So, who is this for? Honestly, it's for the first-time Jordan buyer, the collector who needs the cornerstone of the series, or just anyone who appreciates iconic style. The Jordan Air 1 is a must-have foundation piece. For $180-ish USD, you're paying for history and a design that changed the game.