Keeping your feet dry (or do you not even care?)
I keep extra socks at work, and typically turn my commuting socks inside out and place them and my shoes on top of my computer tower under my desk to dry them out. When the weather goes chilly, I adopt these techniques:


polypro sock liners
wool socks
plastic bag keeps cold water out, blocks cold breeze
ankle hiker or other leather shoe
low gaiters, with the tops tucked under my rain pant cuffs


I keep two pairs of commuting shoes in rotation, to give one a whole day to dry out, to try and avoid fungus buildup.

To keep feet warm, I keep my shoes laced loosely, and I avoid tight fitting socks. I want to keep as much circulation in my feet as possible. Your feet will feel colder if you pile on a lot of socks and constrict your circulation.

My old (street shoes) are very old, hardly worth keeping now. I'm days away from getting some Keen sandals and sealskinz socks.

I've read warm recommendations for fleece socks and neoprene socks (neoprene apparently wicks and blocks wind).