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. Final verdict? I'd recommend this "Jordan Air 1" to anyone building a sneaker collection, or someone who values style over supreme comfort. It's a must-have silhouette. However, I'd "not" recommend it to someone seeking a "comfort-first" daily driver, or for actual basketball. Know what you're getting: a legend, not a cloud. Alright, let's get these open. First impression? The Jordan 1 silhouette is "iconic" – no surprises there. This 'Heritage' colorway is clean, and the leather feels decent right out of the box. For around $180 USD, you're paying for that timeless look. It's a classic for a reason. Unboxing this pair felt special. The classic red/black box, the tissue paper... it's a whole vibe. Holding this "Jordan Air 1", the build quality is good – clean stitching, no glue stains on my pair. The leather on the toe box is a bit stiffer than I'd hoped, but it'll soften. Compared to the recent '85 cut models, this Retro High OG feels more accessible – in both fit and that $180 price point. Solid first impression.