Join Date: Jul 2002
Location: Oxford, UK or Mountain View, Ca
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I have tacked this problem in a slightly different way. Neoprene booties work well for the coldest dry weather temperatures here in the UK (if we get below -5 °C it is unusual). Rain, on the other hand, is another problem - cold and wet. In these conditions I wear wool socks - 1 or two pairs, bike shoes, then a plastic grocery bag tied on to each foot, followed up with neoprene booties. This is more comfortable (less sweaty) than putting the plastic next to one's sock inside the shoe plus it also helps keep the shoe dry and warm.
Get a bicycle. You will certainly not regret it, if you live.