Go for a Jordan 38 or a LeBron model. Also, if you need maximum comfort for all-day wear, look at something with newer tech. And, if you're on a tight budget — the resale on these can be high. There are other great AJ1 colorways for less. Who should maybe skip it? If your main priority is modern comfort & performance tech for all-day wear or sports... look at newer Jordan models. Also, if you're on a tight budget and $180 feels steep for a "basic" leather shoe, I get it. The value here is in the heritage, not the groundbreaking features. Just being honest! Let's be honest, the "air jordan 1 chicago" is a grail for many. Unboxing it feels special. The design is simple yet powerful, making it incredibly easy to style with jeans or shorts. However, the insole is pretty basic, so don't expect cloud-like comfort. Compared to a Jordan 3 or 4, it's a much more "grounded" experience. It's perfect for collectors and casual wearers who value looks. If you need max cushioning, this isn't your shoe. On feet now. Gotta be real – the comfort on the "air jordan 1 chicago" isn't modern. It's a flat, firm ride, which I actually don't mind for short wear. The lockdown is great, though! The ankle collar and laces really hug you. If you're used to plush Jordans like the 3s or 13s? This'll feel stiff. But that's not really the point of this shoe, you know?