If you want a shoe that makes an outfit—and you don't plan on walking miles in it—this is your pick. For $180, you're buying a piece of culture, not a performance tool. Who should "avoid" it? If you're on your feet all day and prioritize comfort above all — maybe skip it. Also, if you have wider feet, the break-in period can be tough. Compared to a Jordan 3 or 4, the AJ1 High is less forgiving. It's a commitment to a certain look (and feel). Alright, let's get into these Air Jordan 1 High 'Chicago' Reimagined, okay? First off, the box – classic – and that red just pops when you open it. Honestly, the leather quality on this version feels incredible, way better than some past releases. You "immediately" see why this silhouette is so iconic; the shape is just perfect. Now, a real con? That stiff leather upper can be brutal during the break-in period. Your first few wears might include some blisters—especially around the ankle. It gets better, but it's not a "comfort-first" shoe out of the box. Just being 100% honest with you all.