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. After wearing these Jordan 1s for a bit, the leather does break in nicely. The fit is true to size, good width. The grip is decent on dry surfaces. Is it worth the price? For this colorway and quality, yes – if you love the design. But at retail or slightly above; I wouldn't pay a massive resell premium for the basic tech inside. 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. Alright, let's get into these Jordan Air 1s in the 'Chicago' colorway. First off, the box is classic & the leather quality? Honestly, solid for a GR. That bright white & "Fire Red" combo just pops on camera! Sizing is TTS for me. The silhouette is, of course, iconic — but the real test is on-foot... which brings me to my next point.