That narrow toe box is no joke. I'd suggest trying a half-size up. The "upside"? Once broken in, the leather molds to your foot nicely. The design is timeless — it's why we're still talking about it decades later. Just know your foot shape before dropping $180+ on these. Final verdict on this pair? For collectors and style-focused folks, the "Jordan Air 1" is an easy recommendation. It's the blueprint. But "really" consider your use case. Are you walking miles daily? Maybe not the best. Want a shoe that defines a genre of culture? This is it. Do your research, try them on if you can, and you'll know. Who should maybe skip? Hardcore comfort seekers, or if you need "tech" in your shoes. Also, if you're on a tight budget – there are more comfortable options at this $180 price point. But you're not really buying comfort; you're buying a piece of culture. The Jordan 1 is about the look and the feel of wearing a legend. Bottom line from my experience: The "Air Jordan 1" is a "cultural icon" first, a sneaker second. Don't buy it for tech—buy it for the statement. It works as a daily wearer if you accept its classic feel. For the "Jordan" series enthusiast or style maven, it's an easy recommendation. Just know what you're getting into: timeless design, not modern comfort. Hope that helps