Up here we don't get a lot of really cold ( < 20F ) weather, but most of the winter is low 30s and raining.
I wear:
- polypro sock liners
- smartwool socks
- shoes with enough room that they're not tight (poor circulation will make your feet cold no matter how thick your socks are.)
- goretex wind/rainproof shoe covers
I find this combo to be good all the way down to freezing. Then I switch the shoe covers for Bellwether No-Aqua fleece lined booties.
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"I feel like my world was classier before I found cyclocross."
- Mandi M.