Originally Posted by reverborama

I wear thick wool socks but the real trick is my Lake boots. They are roomy so the socks aren't compressed, they have an insulated insole so the cleat doesn't transmit cold as well, they come up over the ankles, and they aren't vented like a conventional bike shoe. If you are trying to cram two pairs of wool socks into your summer shoes you won't have as much luck as a single pair of decent socks. The shoe covers should block the wind but most likely the tight fit of a summer shoe and no insulated insole is probably the real problem.