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. Is it worth the price? At around $180 USD, it's a premium for a retro. But you're paying for the history, the look. For a staple in your rotation? I think so. Just know you're buying into a classic design, not cutting-edge comfort. That's the trade-off with this Jordan series icon. Who should maybe skip it? If pure, cloud-like comfort is your #1 priority — this isn't it. Also, if you prefer low-tops or more technical designs, you might not love the feel. It's a style-first, heritage piece. For $180, know what you're getting: an icon, not a tech marvel. Straight up, putting these "Air Jordan 1"s on... the comfort is... okay. It’s a firm ride, folks – don't expect plush cushioning. The ankle collar gives good support, and the overall fit is true to size for me. The break-in period is real, though. After a few wears, they mold to your foot much better. It's that structured, supportive feel the 1s are known for.