funny, I was just thinking about this the other day. Like many, including you, Angie, I wore the soggy bottoms or skirts/dresses with tall boots.
In my defense, I moved to the US in 99 (full-on bootcut era) and before then, I had never lived in a snowy climate. So I didn't know better and I thought soggy bottoms, that's just what everybody does. Some of my pants got pretty ruined, and not just from snow (from stepping onto long bottoms), but surprisingly many were OK. It didn't bother me that badly.
I appreciate the convenience and comfort of tucked-in skinnies, BUT: I also find the look more boring, more of a rut, than when I wore bootcuts and widelegs etc. I felt there was more variety to be had in terms of silhouettes and looks then.