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, so let's get into these Jordan Air 1 'Chicago'! First off - that box? Classic. The "leather" here is solid for a GR release - not buttery-soft, but it's got that nice "sheen". The shape and those iconic red accents just pop. At ~$180 USD, you're paying for the heritage, 100%. It's a piece of sneaker history, right in your hands. Comparing it to other Jordans? Big difference. My Jordan 3s or 4s are way more comfortable. The "jordan air 1" is the foundation, the blueprint. It's lighter than a lot of newer models, which is nice for all-day wear. But if you want that plush, sunk-in feel? Look at later models. This one’s for the history books and your closet. Final thoughts on this Jordan Air 1 High 'Electro Orange'. Unboxing—BAM—that orange is bright! It’s a statement piece for sure. On foot, they feel just like any other Air 1: sturdy, classic. The bold color is the whole story. Pro: you will definitely get noticed. Major con: "very" loud and not versatile. This pair is for the confident style innovator, "period". If you like to blend in, this $170 Jordan Air 1 is not your move. So, know your style before clicking 'add to cart' on this one