The break-in period is real - these can feel stiff. If you need cloud-like cushioning, this ain't it. Also, the ankle collar can rub some people the wrong way. And, let's be honest, at this price point in the "Jordan series", you're partly paying for the heritage, not for cutting-edge performance features. Alright, so we're unboxing the "classic" air jordan 1 retro high og in the "Chicago" colorway. First impression? The leather quality feels solid – not super buttery, but good for a retro. That high-top silhouette is just iconic. At around $180, you're paying for the legacy. Sliding them on, the ankle padding is great, but the break-in period is real – expect some stiffness initially. Okay, on-feet time with the Air Jordan 1 Retro High OG. Let's be real—the comfort isn't modern. It's a firm, supportive ride, not a plush one. The ankle collar gives great lockdown, but it "does" take some breaking in. The silhouette, though? Unbeatable. It makes your outfit instantly look cooler. If you want cloud-like comfort, look elsewhere. But for style & legacy, it's a 10/10. Sliding these on for the first time? Here's the real talk. The "Air Jordan 1 Retro High OG" is NOT a comfort shoe. It's firm, the ankle collar is stiff, and it needs a serious break-in period. But the lockdown? Excellent. My foot feels secure. Compared to a modern Jordan like the 36, it's night and day in terms of cushioning. That's just the nature of this classic design, you know?