The high-top shape just does something for your whole fit – it's legendary. I've worn a lot of Jordans, but the "Air Jordan 1" profile is unbeatable for a clean, stylish look. The 'Black White' color pops against jeans or sweats. It's a shoe that makes an outfit, you know? For $180, you're getting a wardrobe staple. The leather creases, sure – but that's part of the story. 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. Comparing it to something like a Jordan 3 or 4? The Jordan Air 1 is noticeably less cushioned and more rigid. But that’s also why it’s lighter and feels more connected to the ground. It’s a different experience entirely—one rooted in history, not modern tech. If you want plush comfort, look elsewhere in the Jordan series. Conversely, who should maybe look elsewhere? Hardcore comfort seekers or performance basketball players. This is a 1985 design— it’s not built for today's game or for all-day walking comfort. If your priority is a pillowy, energy-returning feel straight out of the box, you might be disappointed. There are simply better modern options for that specific need.