Love the look, always will. But the "comfort"... it's "flat". Compared to even a basic AJ3, there's less cushion underfoot. It's a trade-off: iconic silhouette for modern comfort. For short wears or style shots? Perfect. For all-day concrete pounding? Your feet might ask for a break. Just being honest! 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. Alright, on-foot first impressions: The comfort is... classic. Don't expect modern foam, you know? It's a firmer ride—that's just the Air 1 DNA. The ankle collar locks you in nicely, though. For walking around, style > squishy comfort. If you want plush, look elsewhere. But for that timeless look? It delivers, every time. Let’s talk materials. For the price – $180 USD – the materials are acceptable. They're not premium, but they're consistent. The advantage? This classic "Jordan Air 1" colorway hides minor imperfections well. The disadvantage? They might not age as gracefully as a higher-tier leather. But honestly, most people won't notice. On foot, from a few feet away, they look flawless and absolutely fire with so many fits.