The "first" thing you feel is the "insole" – it's "way" more cushioned than a standard AJ1! The upper uses more stretchy materials too. It's a "modern twist" on the classic. The "huge benefit" is, of course, the comfort – you can actually walk in these all day. The "compromise"? It "doesn't" have the exact same stiff, structured look of the OG. If you've always loved the "Air Jordan 1" style but hated the feel, "this" is your shoe. Traditionalists might find it "too" different. Just got the Jordan Air 1 'Stage Haze'. ~$170 for this black/white/blue mix. Super clean box presentation! Sliding them on... the leather is stiff at first, needs a break-in. The fit is TTS for me. I love how the blue hits add personality – not too loud, not too plain. Great summer sneaker. Compared to all-white Air 1s, these have more character. Downside? The white panels will get dirty fast. If you're a perfectionist about cleanliness, maybe think twice. Otherwise, a great pick. Final verdict? For me, it's a yes. 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. Who should maybe skip? Hardcore comfort seekers, or if you need "tech" in your shoes. Also, if you're on a tight budget – there are more comfortable options at this $180 price point. But you're not really buying comfort; you're buying a piece of culture. The Jordan 1 is about the look and the feel of wearing a legend.