This shoe, especially in a neutral color like this 'Shadow' 2.0, goes with literally everything. Jeans, joggers, shorts—it doesn't matter. The "Air Jordan 1 High" is a wardrobe staple. The cons? That stiff break-in period can be a pain for some. Final verdict: Get a pair of air jordan 1 highs if you're building a classic sneaker rotation. It's a must-have. But—if you prioritize modern tech and soft cushioning above all else, you might be disappointed. For the right person, though? It's an absolute legend. So I'm lacing up the classic Air Jordan 1 High 'Chicago' (2022 version). The red just pops on camera, it's unreal. First impression? It's "the" blueprint. On foot, it's exactly what you expect: iconic, but not what I'd call comfortable for long walks. The pro is its timeless status in the Jordan series. The con is the price—resale is steep. If this is your grail, go for it. If you just want a comfortable red shoe? There are better, cheaper options. It's a heritage piece, first and foremost. Here are my "Air Jordan 1 Highs" on foot. This is the 'Dark Mocha' version. The quality of materials here is a standout pro—the suede feels premium. Compared to a mid-top, the high-top collar gives that classic, locked-in feel. Is it worth the Jordan series premium? For this colorway, yes. But be warned: they can feel heavy and clunky if you're used to lightweight sneakers. Perfect for fashion, not for performance hooping.