It works with almost any fit. But be honest about your needs. If you prioritize ultimate comfort above all, this isn't your shoe. You're buying the look, the legacy. For me, having at least one pair — like these 'Royals' — is essential. Just know what you're getting into: a firm, iconic experience, not a cloud-like ride. Got the classic 'Chicago' Jordan Air 1 Retro High OG. Man, unboxing this legend... the red just "pops" against the white. It's history in a box. On foot, it's the same familiar fit—secure, but don't expect cloud-like comfort. It's about the look and the legacy, "period". Comparing it to newer Jordan models with Zoom? No contest on cushion. Pro: unbeatable iconic status. Con: premium price (often over $200) for a "firm" experience. A grail for collectors, but a practical choice for daily beaters? Maybe not. Just copped this newer Jordan Air 1 'Mid' version in 'Wolf Grey'. At a lower price point (~$115), expectations are different. The materials are more synthetic, but the shape is still there! On foot, they feel... fine. It's a budget-friendly way to get the iconic look. If you're a purist about materials & OG highs, skip it. But for a beater pair? Not bad at all. Daily wear test for the Jordan Air 1. After a full day, my feet are "ready" for a break. The lack of arch support and firm midsole is noticeable. But! The style points are through the roof. They look great with jeans, shorts, you name it. Durability is a plus—these things are tanks. So, who are they for? People who prioritize style > all-day comfort. Not for you if you're on your feet 12 hours. It's a trade-off with this iconic Jordan series model.