I wear wool (Smart Wool) socks year round rain or shine. Covering up the holes in the bottom of your shoes will help as well. Masking tape will work just fine!

Just got some Merino wool underwear from REI- long sleeved top and tank tops (on sale). Have worn the sleeved top under my jersey 3 times now in 35-40 degree weather, in rain showers, and in wind. Works great!

I also bought a Goretex parka at Performance Bike a couple of years ago that I use for cold days. Since Goretex breathes, it helps with condensation. I'm not nearly as wet using this plus my warmest long sleeve jersey and my wool undershirt.

I recommend wool for year round cycling. It's been great for my feet even in 90 degree weather! I'm going to try the long sleeved wool top for the Death Valley century in March. That will be the warm weather test!