Honestly, the comfort is... "fine". It's not a modern cushioning setup, so don't expect bounce. The ankle collar gives good support, and the fit is true to size for me. The "jordan air 1" is about style first, feel second. It’s a bit stiff initially - they definitely need a break-in period. Just being real with you all. Unboxing this 'University Blue' "Jordan Air 1" and... wow. That color is even better in person. The white leather panels are clean. My favorite part? How it looks on camera. The shape just "photographs" so well - a true testament to the design. For content creators or just IG fits, this shoe is a "tool". It simply works. 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. Conversely, who should "skip" it? If you have serious foot issues, need arch support, or are buying sneakers purely for athletic performance or all-day walking comfort—this isn’t it. Look at the React or Zoom lines instead. The Jordan Air 1 prioritizes form... over function, in the modern sense.