Avocet,
I think Kawaihae hit the nail on the head concerning looser-fitting pants. Guys (and women, of course) dress how they do with the main aim of attracting mates. If it doesn’t work, it goes out of style.
But I’m sure you’re right: Some women, at least, would prefer to see a guy’s butt and package. I’ve always thought that only guys with larger builds than mine could get away with this, but I might just be perceiving myself inaccurately, like so many of us do regarding our dick sizes. A big problem I’ve always had with tighter pants is that the only look good with tighter shirts — and, although I’m happy with the way my body looks WITHOUT a shirt, when I’m wearing a tight shirt I end up looking truly scrawny. I’ve always associated this look (accurately, I think) with gay men’s fashion — not too helpful for attracting women.
I think that a boot-cut pant might work better for the build of my legs. Somebody mentioned a boot-cut Levi’s. What specific number is that in their line, and where could I find something like that? I’m interested in trying some less saggy clothing :) .