I have toe covers and booties. I wear the toe covers with wool socks when it's in the low fifties or so. I wear the booties when it's in the forties or below. Sometimes, I wear both! Or, I have been known to slip a chemical warmer in between socks and shoes and then the booties if it's in the thirties...
I can stand the cold on my face, but if my feet are cold, forget it.