I wear jeans and tall dressage boots sometimes. they're just fine and comfy. what I do, to keep them from bunching is just to wrap the... flaired end around my ankle (kinda hard to describe I suppose) and then I pull my socks over that (I wear socks that go about half way to the knee, when I'm at the barn) and then slip the boots on. And they look fine too, just like breeches made out of denim basically.
Heir To Liberty || aka Liberty || Bay Arabian Gelding || Dressage
Moonlight Mystique || aka Mysti || Chestnut Arabian Mare || Western
Regent Psyerra || aka Psyerra || Chestnut Arabian Filly ||