The height gives great ankle support for casual wear. But let's talk comfort – or lack thereof. Compared to newer Jordan models with Zoom air, these are pretty flat and firm. It’s a classic basketball shoe from the 80s, so manage your expectations. The pros? Timeless style and unbeatable versatility. The cons? Your feet might ache after a long day. Alright, let's get into these Air Jordan 1 Retro High OG 'Chicago's. First impression? The box, the red/white/black colorway—it's iconic for a reason. On foot, the ankle collar needs a bit of break-in, but the leather quality on this retro is solid. Compared to a modern Jordan, like a 36, the tech is obviously dated—it's a firm, flat ride. But that's the point. If you want history on your feet and a timeless look, this is it. If you need cushioning for all-day comfort, maybe look elsewhere. Let's talk about actually wearing these. The air jordan 1 retro high og ("Shadow" colorway here) is a statement. On foot, they feel substantial – you "know" you're wearing them. The flat, firm midsole isn't for long walks, in my honest opinion. But visually? They make any simple outfit pop. Compared to a Jordan 1 Low, the high-top offers more ankle... presence. It's a trade-off between style and mobility. So, my recommendation? If you love classic basketball style, you need one. If you only wear ultra-boosts for comfort, you might hate it. The air jordan 1 retro high og is for the style-focused wearer. It's a piece of wearable history. Don't overthink it — if you like the look, you'll love wearing it. That's my honest take.