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. On foot, this 'University Blue' pair really pops. The Jordan Air 1’s high-top profile just looks so good from every angle, especially on camera. The colorblocking is simple but effective. However, the flat midsole can feel a bit unforgiving if you’re walking on concrete for hours. It's a trade-off for that timeless, iconic aesthetic. Final verdict? For me, it's a yes. 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. Major pro: the style is unbeatable. This 'Bred' colorway of the Jordan Air 1 is just iconic. You can dress it up or down. Another plus? Durability. The construction is tried and true. After break-in, they become a reliable go-to in your rotation. For $190, you're paying for legacy and a design that never quits.