Loulou, I have been a closet legwarmer wearer for years. I wear them over knee high boots (which are worn over skinnies). I also wear them with ankle boots and skinnies (over both). They do look better with a heel, even a small one. I don't really like how they look with my riding boots, but that doesn't mean they won't look good with ANY riding boots. Mine just don't have a nice enough shape to them.
They also look great with leggings and pumps or flats though it might send some into 80's overload. You and I were both kids then so I think we have a good excuse to try them this time around
I have tried them with skirts, but I just felt too girlish. I'm petite and young so I am overly conscious of looking like a schoolgirl though. Might work on someone who is clearly too old and tall to be in high school.
