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. Who should "skip" it? People seeking max comfort or performance basketball shoes. The fit can be narrow, and the cushioning is basic. If tech is your main priority in 2024, this retro Jordan Air 1 isn't for you. It’s about form over cutting-edge function. Sliding these on... yeah, the fit is TTS for me. Initial comfort? Don't expect anything revolutionary – the Air Jordan 1 is famously firm underfoot. It's about support, not plushness. The ankle collar gives great lockdown, though. If you're coming from a modern runner or even an Air Jordan 4, the break-in period for this Jordan Air 1 might feel a bit... "stiff" at first. My final take? At around $170-$200 for most retros, the value is in the design. You're buying into a legend. For a first Jordan? It's a perfect start. For a veteran? It's a necessary classic. Just go in knowing the feel is classic, not cloud-like. Would I recommend it? Absolutely – but with those caveats.