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. Let's talk durability – the Jordan Air 1 is a tank. The solid rubber outsole, the sturdy build... these will last years. The creasing becomes part of the character. A potential downside for some? The high-top can feel restrictive if you're not used to it. But for ankle support and that iconic look, it's a worthy trade-off. 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. Who is this for? Honestly, the "jordan air 1" is perfect for the style-focused person. It's a fashion staple first, a sneaker second. If you're building a rotation of classics, this "needs" to be in it. Not for who? Serious runners or gym-goers. This isn't a performance shoe—it's a piece of history you walk in.