I rode in tall boots exclusively growing up. I thought breeches were comfortable and I think they were so easy to ride in.
When I joined the polo team in college I went to jeans and half-chaps because that's what everybody wore (and we did a lot of dirty barn chores so jeans were more practical).
Now, when I take lessons as an adult I still use the half-chaps. I honestly don't like riding in jeans that much and find it less comfortable than breeches, but I'm also not so comfortable wearing skin tight pants around the barn anymore