My experience using my summer shoes and trying to get warm feet has been poor. I buy the same shoes ~ a size larger for cooler weather. I can stretch their range by double bagging my feet in produce bags; one against my skin and one over my warm sacks with a very thin old man's dress sock to hold it in place. This keeps outside air off the socks and the socks 100% dry so using their full insulating value. Still only what, an 1/8" of insulation. Not much. Warm leggings help me a lot.

Real warm feet in cold weather never happened until I got boots. My 45 North Fasterkatt boots work well to the mid 20s are are far warmer than any cycling shoe system I ever came up with. (A lot faster to put on too.)