It’s that kind of shoe. The design is so timeless. Versus a Dunk? The AJ1 Chicago has more heritage, in my opinion. Pro: legendary status. Con: the sole is flat and hard for long walks. Know what you're buying into. My final take? If you love the culture, this is a must. The Air Jordan 1 Chicago is "the" definitive colorway. You feel connected to that legacy when you wear them. Are they the most comfortable Jordan 1? No. But the look, the prestige... it's worth it for the right person. Just know what you're getting into. Sliding these on for the first time? Honestly, the fit is snug - a true-to-size fit for me. The "Air Jordan 1 Chicago" isn't known for plush comfort, & that's the truth. You feel the court heritage; it's a firm, supportive ride. The high-top collar gives good ankle "lock-down", but don't expect Boost-like softness. After wearing them all day, here's my real take. The leather upper—on this Chicago colorway—breathes okay, but it's not a summer shoe. My feet were warm. The grip is surprisingly good for a casual wear. Compared to a Jordan 3 or 4? Much less padding. You feel the ground more. The pro is the unbeatable confidence they give you. The con is the literal pain during the break-in period. It gets better, though!
