You're not buying it for revolutionary comfort. You're buying the look, the history. My pair creased after one wear – and I'm okay with that! It adds character. The flat sole is great for board feel if you skate, but not for all-day support. For $180, it's a fashion piece. It's perfect for sneakerheads and style-focused folks. If you prioritize cushioning above all else, look at the Jordan 3 or 4 instead. Conversely, who should "avoid" it? If you’re on your feet all day and need cloud-like comfort — look elsewhere (maybe a Jordan 13). If you have very wide feet, the narrow fit can be "truly" uncomfortable. This shoe demands a bit of a sacrifice for the sake of style. Be honest with your needs. On foot, the look is undeniable. This "air jordan 1 high" just makes any simple outfit pop. The high-top silhouette gives you that effortless, slightly-tough vibe. In photos or on video, the red/white/black contrast is super clean. It's a design that works off-court, for sure – more about style than sport these days. So I finally got my hands on this pair... the Air Jordan 1 High in the 'Chicago' colorway. Unboxing it is a moment, I'm not gonna lie. The red just pops! On feet, you immediately feel that iconic, slightly elevated silhouette. The cushioning? It's firm... very 1985. Don't expect Boost or React here. The ankle support, however, is fantastic. It's a perfect shoe for style and basketball culture history, but as a all-day, everyday sneaker? There are definitely more comfortable options out there.