The biggest pro is obviously the timeless design – it goes with "everything". The quality on this 2022/2023 release is solid for the $180 USD price tag. The con? The comfort, 100%. If you're used to modern sneaker tech, this will feel like a brick. It's not a "all-day walking shoe" for most people. That’s just the reality of the Jordan 1 platform. So, should you cop? If you've wanted a Chicago 1 forever – yes, this is your chance. It's the definition of a classic. If you need premium materials and modern comfort, maybe wait for a sale. Personally? I'm keeping my pair on ice for special occasions. The Air Jordan 1 in this colorway is simply eternal. The red on this Air Jordan 1 Chicago really pops in sunlight – looks amazing on video. On foot, it's not a bulky shoe, which I like. The toe box has that classic shape. A clear advantage is its status; it's instantly recognizable. A potential downside? The creasing. These will show wear quickly. If you're super precious about keeping kicks pristine, this might stress you out. Potential con? The lack of modern comfort tech. If you're on your feet all day, these aren't your best pick. Also, the leather can crease noticeably (but that's part of the charm for some). And at around $180 USD, it's an investment for a shoe that’s not “technically” advanced.