You're paying for the legacy, the look, and that unbeatable versatility. Is it the most comfortable shoe in my closet? No. But is it one of the most worn? Absolutely. It just works. Major pro: UNMATCHED versatility. This 'Shadow Grey' pair? I can dress it up a bit or keep it super casual. The color blocking is just genius. Another pro is durability – the materials, while sometimes basic, can take a beating. These are shoes you can actually wear regularly without babying them (aside from the creasing!). Now, a real con for some people: the fit. It can be narrow, especially in the toe box. I'd say go true to size, but if you have wide feet, maybe try a half-size up. Also, that high-top collar can rub against your ankle at first. It's not for everyone – if you prioritize all-day cloud-like comfort, look elsewhere. This is a style-over-comfort pick, period. Final, real talk. I love my "Jordan 1s". They're comfortable "enough" for casual wear. The high-top provides good ankle support – a clear "advantage". But that flat footbed? It's a drawback for long days. My advice: if you appreciate heritage and style over cutting-edge tech, cop a pair. If comfort is your #1 priority, maybe look at the Jordan 13 or something more modern.