It goes with everything. The con? That same classic build means it's not the most comfortable for all-day wear – the footbed is pretty flat. If you need arch support or plush cushioning, this isn't your shoe. It's for the look, not long-distance comfort. Alright, let's get into these Jordan Air 1 'Chicago' lows, priced at $150. First impressions? The box and presentation are classic. The color-blocking is just iconic — that white leather base with the red and black hits is instantly recognizable. On foot, it's a bit stiff initially, but that's normal for a Jordan Air 1. For me, the silhouette is the real star here — it just looks so clean from every angle. 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 direct sunlight, the materials really show up. The leather has a nice grain, and the stitching is clean on my pair. Some retros can feel cheap, but this 'Bred' "jordan air 1" execution is solid. It feels durable, like it'll age well with wear. A good sign for the price.