The Jordan 1 High OG 'Chicago' is worth it. It's a cornerstone. The look, the history, the sheer versatility… it's unmatched. Just go in knowing the comfort is classic, not modern. As an all-time-great design? 10/10. Here’s the honest take: The biggest pro of the Jordan 1 is its legacy & style. It goes with everything. The con? That same classic build means it's not the most comfortable for all-day wear – the footbed is pretty flat. If you need arch support or plush cushioning, this isn't your shoe. It's for the look, not long-distance comfort. Here’s a real downside: that classic toe box creases... "fast". If you’re someone who hates that look, this might bug you. Also, the ankle collar can rub a bit at first until it breaks in. It’s not for folks seeking ultimate comfort or a pristine, uncreased look long-term. You have to embrace the wear. Let's talk durability – the Jordan Air 1 is a tank. The solid rubber outsole, the sturdy build... these will last years. The creasing becomes part of the character. A potential downside for some? The high-top can feel restrictive if you're not used to it. But for ankle support and that iconic look, it's a worthy trade-off.
