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. Sliding these on... wow, the fit is snug. True to size for me, but they need a little break-in. The ankle collar provides great lockdown – no heel slippage at all. Compared to some newer, more cushioned Jordans, the "Jordan Air 1" is firm. Let's be real: you're not buying these for cloud-like comfort. You're buying them for the look and the history. The weight feels good, though – not too heavy on foot. Check out this "University Blue" "Jordan Air 1"! "Straight out" of the box, the colors pop "so" well. This is one of those pairs that just looks "better" in person, you know? On feet, the fit is perfect for me – a true sneakerhead staple. The "advantage" of the "Air Jordan 1" is its timeless design; it's a piece of history. However, the "arch support" is basically non-existent, which might bother some. If you're new to Jordans, this is a "fantastic" first pair. If you have "multiple" 1s already, it's just another (awesome) color. At "$170", it's a solid pickup. Let's talk about the "fit" of the Jordan Air 1. I went true-to-size, and the length is perfect. The width is "snug", not tight. For some with wider feet, this could be an issue—consider sizing up half. The ankle support is fantastic for a lifestyle shoe. Stepping out, you feel "connected" to the ground. It's not a squishy, modern sneaker. You buy the Jordan Air 1 for its legendary look and cultural weight, period. It's a wardrobe essential, not a comfort innovator.