The main one? That flat, firm midsole. If you're on your feet all day, this isn't your go-to "comfort" shoe – you'd want something with more tech. Also, the toe box creases... it's gonna happen, it's part of the leather's charm (or annoyance, depending on your view). So, this specific Jordan Air 1 model isn't for the comfort-first crowd. Alright, let's get into these Jordan Air 1s in the 'Chicago' colorway. First off, the box is classic & the leather quality? Honestly, solid for a GR. That bright white & "Fire Red" combo just pops on camera! Sizing is TTS for me. The silhouette is, of course, iconic — but the real test is on-foot... which brings me to my next point. On feet now, and the ankle support is noticeable – in a good way. The padding locks your heel in. Visually? This shoe pops. The high-top design and classic color blocking just work with… almost anything. It's a wardrobe staple, honestly. A solid foundation for any rotation. Who should maybe skip it? If pure, cloud-like comfort is your #1 priority — this isn't it. Also, if you prefer low-tops or more technical designs, you might not love the feel. It's a style-first, heritage piece. For $180, know what you're getting: an icon, not a tech marvel.