You can wear a pair from 5 years ago and it still looks current. The "con"? They can crease... a lot. Some love that "lived-in" look, some hate it. Using force fields helps, but it changes the fit. It's part of the deal with this model. Just something to know before you cop! Final take: I love having a pair of Jordan 1s in my closet. They're reliable. But be real with your expectations: they're not the comfiest. The break-in is real, but once they mold to your foot? You've got a classic. I'd recommend them – but with that caveat upfront. Let's talk comfort — realistically. The "Jordan Air 1" is "not" a modern performance sneaker. The cushioning is firm. If you're used to React foam or Air Max bubbles, you'll find these pretty stiff, especially for long days on concrete. That's the trade-off for the look. The plus side? That firmness provides great stability, & the leather upper will mold to your foot over time for a better fit. Honest take: The Jordan Air 1 is a legend, but it’s not for "everyone". If you prioritize supreme comfort above all else, maybe look at the Jordan 3s or some New Balance models. But for that iconic, street-ready style—the Jordan 1, especially around this $180 price point, is still a solid entry in the Jordan series.