It works with almost any fit. But be honest about your needs. If you prioritize ultimate comfort above all, this isn't your shoe. You're buying the look, the legacy. For me, having at least one pair — like these 'Royals' — is essential. Just know what you're getting into: a firm, iconic experience, not a cloud-like ride. Not everyone will vibe with it, though. If your priority is cutting-edge comfort or max cushioning for all-day wear, look elsewhere. This isn't that shoe. Also, for some, the $190+ price for a "basic" leather shoe might feel steep. You're paying for the icon status. So, think about what you "really" want from a sneaker before copping this Jordan Air 1. On feet now. 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. On feet now, and the ankle support is noticeable – in a good way. The padding locks your heel in. Visually? This shoe pops. The high-top design and classic color blocking just work with… almost anything. It's a wardrobe staple, honestly. A solid foundation for any rotation.