Also, if you have a wider foot, the "Jordan Air 1" can feel narrow in the toebox — it might require a break-in period or even sizing up. It's a classic, but not necessarily the most "accommodating" shape for everyone. That's a real point to consider before buying. 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. In summary: The "Jordan Air 1" delivers exactly what it promises — a timeless look, great materials (on most colorways), & unbeatable versatility. The downsides? The firm ride & potential break-in time. For $180, it's a staple. If you love the design, you won't be disappointed. Just manage your comfort expectations & you'll have a shoe that lasts for years, both in build & in style. So — worth it? My personal take is yes, especially this colorway. It's a workhorse in your closet. The Jordan Air 1 isn't the comfiest, but man, does it make you "feel" cool putting it on. For that iconic status / daily wear combo, it's tough to beat. Just maybe... wear thicker socks. You'll thank me later