First impression? The classic "Air Jordan 1 High" silhouette is just "timeless". This 'Heritage' colorway, with that Chicago-esque vibe, pops right out of the box. The leather feels decent for a GR release. At around $180 USD, it's what you expect. It’s a solid start for any Jordan collection, honestly. Who should buy this ‘Air Jordan 1 High’? Anyone building a foundational sneaker rotation. It’s essential. It works for almost any casual outfit. Who should "skip" it? If you’re new to sneakers and on a tight budget, maybe start with something more comfortable. Also, if you hate breaking shoes in – the stiff start might frustrate you. Comparing it to a ‘Jordan 1 Low’, the High just feels… more substantial. The security around the ankle is a game-changer for some. Versus newer Jordans? There’s no Zoom air here, no crazy tech. It’s simple, and for many, that’s the point. If you want modern performance, look at the ‘Jordan 37’. If you want timeless style, this ‘Jordan 1 High’ is your answer. Now, the cons are real. That break-in period can be rough—hello, heel blisters! The toe box creases easily, which some hate (I think it adds character). And again, for $180 USD, you're not getting modern comfort. If your priority is all-day walkability, this might disappoint. It's a style-first shoe.