That's the trade-off. You get that amazing ankle lock / support, but the cushioning? It's firm. It's a classic basketball shoe from the 80s, so manage those expectations. If you're coming from something like a Jordan 3 or a modern runner, you'll feel the difference. But for style? Unbeatable. The silhouette just works. Let's talk pros. The biggest advantage of the Nike Air Jordan 1 is its versatility and iconic status. It's a sneaker legend for a reason. The colorways are endless, and the design is simple enough to dress up or down. Durability? The leather upper holds up well over time. It's a true wardrobe staple, no question. Got this "Nike Air Jordan 1" in the 'Stage Haze' colorway. It's a messy, artsy look that I actually dig! For ~$180 USD, it's a statement piece. Fit is TTS, with that typical snug forefoot. What I like? It's different from your standard red/black/white "Jordan 1". What might turn people off? The distressed look isn't for everyone. Perfect for someone wanting to stand out in the "Jordan series". Alright, let's get this "unboxed". First look at this Air Jordan 1 'Chicago'... "damn", that color-blocking is just iconic. The leather feels premium straight out the box. Slapping these on, the ankle support is insane, but that forefoot? A "bit" stiff, honestly. For $190, you're paying for the history & the style—not cloud-like comfort. If you want a piece of sneaker history that goes with "everything", this is it. If you need all-day cushion, look elsewhere.