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. Conversely, who should maybe look elsewhere? Hardcore comfort seekers or performance basketball players. This is a 1985 design— it’s not built for today's game or for all-day walking comfort. If your priority is a pillowy, energy-returning feel straight out of the box, you might be disappointed. There are simply better modern options for that specific need. Side-by-side with my other Jordans, the "Jordan Air 1" stands out for its simplicity. No crazy details – just pure, effective design. The insole is basic, no fancy tech there. But man, that high-top hug is real! It's a confident feeling when you lace them up tight. For basketball? No way – it's 2024. But for making a simple outfit look considered and cool? It's almost unbeatable, especially in this clean black-and-white OG scheme. Let's talk about the Jordan Air 1 'Light Smoke Grey'. This is a perfect example of a non-OG colorway that just works. The materials feel premium, & the grey nubuck is buttery. On feet, they're surprisingly light! A major pro is how easy they are to style for a casual fit. A con? That outsole picks up dirt like crazy. If you want a low-maintenance shoe, maybe look elsewhere.