It goes with literally almost anything: jeans, shorts, joggers. The colorway is just so versatile. On camera, that bright 'Chicago' red really pops. It's one of those sneakers that always gets a second look on the street, you know? Who is the "Air Jordan 1 Chicago" for? Sneakerheads, obviously. It's for anyone who wants "the" most recognizable sneaker of all time. Who is it "not" for? People seeking modern comfort or those on a tight budget. For $180, you want performance? This ain't it. You want a legend in your closet? This is it. Okay, let's unbox these legends. The first thing you see is that iconic "Chicago" red & white box. Pulling out the Air Jordan 1 'Chicago'... wow. The color blocking is just perfect. The leather feels stiff "at first", but you know that's how these 85'-inspired ones are built. For $180, you're paying for that heritage silhouette, 100%. Who should skip it? If comfort is your #1 priority, look at newer models. Also, if you prefer low-tops or more understated shoes, this bold, high-top silhouette might not be your vibe. It’s a loud shoe in terms of heritage, even if the colors are technically simple.