The "Nike Air Jordan 1" works with almost anything. Who should "skip"? If you prioritize cloud-like comfort above all else - look at newer models, seriously. Okay, here's my real take. This "Nike Air Jordan 1" High OG is a legend for a reason. The silhouette is "untouchable"—it makes any outfit better. But let's be honest: the comfort is not modern. It's a flat, firm ride. After wearing ultra-boosts all day, putting these on is a shock. Yet, I keep reaching for them. Why? Pure style and confidence. For $180 USD, you buy the look. It's perfect for someone who values iconic design over all-day comfort. If you need cushion, this isn't your shoe. Is it worth it? If you're building a sneaker collection, 100% yes. The "nike air jordan 1" is a foundational piece. For a first-time Jordan buyer, this "Chicago" colorway (or a similar classic) is the perfect start. It's history you can wear. However, if your priority is gym performance or marathon comfort, this isn't your shoe. Know what you're buying. I've got the Nike Air Jordan 1 Mid 'Banned' here. The black/red colorway is always a winner, and the price point is more accessible at ~$120. First impression? The materials feel a step down from the OG Highs - more synthetic. Comfort is similar to other Mids: good for all-day wear without being exceptional. "Upside": You get that iconic "Bred" look for less cash. "Downside": Sneaker enthusiasts often critique the Mid's quality and altered proportions. This is the ideal starter Jordan 1 for a younger audience or someone testing the waters without a huge investment. Seasoned collectors will likely pass for an OG High version.