I went true-to-size, and the length is perfect. The width is "snug", not tight. For some with wider feet, this could be an issue—consider sizing up half. The ankle support is fantastic for a lifestyle shoe. Stepping out, you feel "connected" to the ground. It's not a squishy, modern sneaker. You buy the Jordan Air 1 for its legendary look and cultural weight, period. It's a wardrobe essential, not a comfort innovator. Alright, let's get into these. First "impression" unboxing this 'Chicago OG' colorway? The classic "Jordan Air 1" shape is just perfect. The leather quality here feels solid—not super-premium, but definitely good for the $175-$200 price point. The red, white, and black combo is simply iconic. It's a piece of history right out of the box. As a foundational "Jordan" silhouette, it sets the standard. Let's be real about the cons. 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. Sliding these on... you gotta remember the Jordan Air 1 is a 1985 design. The tech is basically zero. It’s a firm, flat ride—don’t expect cloud-like comfort. But, the ankle support and that snug, true-to-size fit are actually great for all-day wear. It’s more about style and heritage, not performance cushioning, which is totally fine for its purpose.