This shoe is a canvas. You can wear it with almost anything. The construction, while not ultra-luxe, is durable. It's a piece of sneaker history you can actually wear daily. That's the biggest "pro" for the "Air Jordan Retro 1". It's timeless. You won't look back in 5 years and think, "what was I wearing?" If you're new to sneakers, the Air Jordan 1 Retro is arguably the best place to start. Its design influence is everywhere. However, the flat, firm insole might not be for everyone, especially if you're on your feet all day. I'd recommend them for collectors & style-focused folks, but maybe not for pure comfort seekers. Who should "avoid" it? Hardcore comfort seekers, for sure. If your priority is advanced cushioning (like Zoom Air or Boost), you'll be disappointed. Also, if you need a performance basketball shoe – this is "not" it, despite its heritage. It's a lifestyle sneaker now. And if you're on a tight budget & need one do-it-all shoe? The $200 USD price for a "Retro 1" might be steep when more comfortable options exist. The "biggest" pro of any Air Jordan 1 Retro? Versatility. It's a shoe that works with jeans, shorts, or even (dare I say) a casual suit. The high-top design gives that iconic profile. The con is the break-in period – the heel can rub at first. At ~$170-$200 USD, it's an investment in style, not cutting-edge tech. Suits someone building a foundational sneaker collection.