Being in my 40s and in shape, I’m wearing straight fit or slim straight (not skinny). I still have some jeans from the ‘90s but they are more like what the cast of Friends wore. I never did JNCO, but I wore baggy/loose cut SilverTab and the 568 or 569 Levi’s or whatever the numbers were back then for loose/baggy.

Where whatever you want imho, even cargo pants or jorts if that’s your thing, but I hit a certain age (without going into dad jeans territory) that 1. I’m not going to spend a lot of money chasing fashion trends or do it in general, and timeless well-fitting clothes last forever with how I take care of them. 2. Clothes that fit well just look better on me. I grew up going through a very awkward puberty like a lot of us and I got really chubby around 13-15 and wearing baggy jeans and big shirts were in but also a way to hide my body and insecurities and even though I’ve most outgrown that body for close to 30 years I’ve always felt like the fat, short, outcast, while objectively somehow in my mid-40s I look better than I ever have. So I’m going to embrace that wearing clothes that fit and have a more timeless look and feel (and to be clear I also feel more comfortable in “fitted” clothing)