It goes with everything. The con? That same classic build means it's not the most comfortable for all-day wear – the footbed is pretty flat. If you need arch support or plush cushioning, this isn't your shoe. It's for the look, not long-distance comfort. Let's talk pros & cons, straight up. "Pro": The "Jordan Air 1" is a legend. The cultural impact is undeniable, and this release nails the aesthetic. "Con": That classic build means a break-in period. The toe box might feel a bit rigid at first. If you prioritize plush comfort above all else, this might not be your daily driver. It's more for the style & the heritage, which, for many, is totally worth it. 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. Final verdict time. Pros: Timeless design, incredible versatility, true-to-size fit, and strong cultural cachet. Cons: Firm ride, toe creasing, and a premium price for a simple construction. The Jordan Air 1 is a legend for a reason – but it's a style/icon play, not a tech marvel. Know what you're getting into, and you'll likely love it.