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. Yo, what's up everyone? Just copped the Jordan Air 1 Mid 'Shadow 2.0'. First thing I noticed out the box was the "quality"—the grey nubuck is really nice! Pulling these Air 1s on, the fit is snug and supportive right away. Visually, they're super versatile. Compared to a bulkier Jordan 4, these are way more sleek for everyday wear. Major pro: goes with "everything". Con? That stiff out-of-box feel. Great starter sneaker, but hardcore comfort seekers might wanna skip. Walking around in them... yeah, you feel every bit of that 1985 DNA. The sole is firm, the ankle support is high – it's a very "grounded" feel. I love the elevated look it gives me, style-wise. But compared to a Jordan 3 or 4? It's less forgiving on the foot, for sure. That's the trade-off for that sleek, low-profile silhouette. If you prioritize looks – win. If you prioritize plush comfort – maybe look elsewhere. Now, the potential downside— and I have to be real with you— is the comfort tech, or lack thereof. If you need modern, bouncy cushioning for all-day wear or long periods on your feet, the "Jordan 1" platform might leave you wanting more. It's a firm, stable base, not a cloud. For some people, that’s a dealbreaker, and I totally get it.