I use standard road shoes but layer the heck out of it.
- Rapha Deep Winter wool socks have wind protection in front and go up to the knees.
- On top of my shoes I put Castelli Estremo covers, the thickest covers I could find.
- For colder than about 25F I add an extra cover on top - an old beater pair of large neoprene shoe covers which fit over the Estremos. I cut off the upper part to avoid constricting the ankle too much - they cover the shoe portion only.
I have goofy-looking club feet with all the layers, but hey my feet are warm! Note this is for Maryland winters, we rarely get into the teens.