I think boots are just extremely uncomfortable and I've never put on a pair of boots I liked on my foot.
I have no problem at all with ankle high shoes, as that is all I wear, they cover all of my ankle.
I don't give two shits what I look like, so that's not the problem, it's just the feel of them on my feet. Heavy, clunky, just don't like them.
I also won't wear anything on a bike that's not covering my ankles and have some sort of support for them.