If you prioritize plush comfort above all else? Look elsewhere. The Air cushioning is minimal by today's standards. After a long day on your feet, you'll definitely feel it. I love my Jordan 1s, but I'm not grabbing them for all-day travel or a festival. They're more of a style-over-comfort pick. Big pro here: timelessness. A fresh pair of Nike Air Jordan 1s never goes out of style. The color-blocking is legendary. They're also surprisingly durable—the outsole is tough. You're investing in a shoe you can wear for years, and it'll still look relevant. That's a major plus in my book for any sneaker purchase. Alright, let's get this "unboxed". First look at this Air Jordan 1 'Chicago'... "damn", that color-blocking is just iconic. The leather feels premium straight out the box. Slapping these on, the ankle support is insane, but that forefoot? A "bit" stiff, honestly. For $190, you're paying for the history & the style—not cloud-like comfort. If you want a piece of sneaker history that goes with "everything", this is it. If you need all-day cushion, look elsewhere. Who should "skip" the Nike Air Jordan 1? If your main priority is all-day comfort – like, you're on your feet for hours – look at something with more cushioning. Also, if you're on a tight budget, the retail price is steep for the tech you get. And if you hate noticeable creasing on your shoes, this leather will show wear quickly.