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. Now, the potential downside— and I have to be real with you— is the comfort tech, or lack thereof. If you need modern, bouncy cushioning for all-day wear or long periods on your feet, the "Jordan 1" platform might leave you wanting more. It's a firm, stable base, not a cloud. For some people, that’s a dealbreaker, and I totally get it. The major "pro"? Versatility. This 'Black Toe' colorway goes with literally everything—cargos, jeans, shorts. It’s a wardrobe staple. The cons? That leather creases—and it shows. If you're super precious about keeping your kicks mint, a Jordan Air 1 might stress you out. For me, they look better with wear. On feet, the Jordan Air 1 just works. The high-top silhouette gives you that classic look – it's timeless, man. They photograph incredibly well; the shape is perfect. Compared to some of the newer, bulkier Jordans, the 1 has a sleekness to it. Major pro? Versatility. You can dress 'em up or down so easily.
