I first started wearing Vibram FiveFingers minimalist shoes in October of 2009, but every year, I have not worn them in the winter months when the temperature drops below freezing and there is snow or ice on the ground (January, February).
Somehow, today as I saw a bit of snow fall outside (with very little accumulation), I decided to do a short run (less than two miles) in my Bikila LS shoes while returning some items to the local library, to get a taste of whether it is practical to try regular winter running in these shoes, as the temperature drops and more snow falls.

Last year, sometime in early spring, I ran in regular mono-toed running shoes for the last time in my life. Every “normal” running shoe I have ever used (and I have worn probably two dozen different models in the past decade) had caused me some kind of disappointment. Switching completely to Vibram FiveFingers shoes had solved all my problems.
I have been fearful, however, of winter running in FiveFingers. Would my feet freeze? How would I handle cold water? Snow? Ice?
Today I decided that the only way to answer the questions would be to go out there and start experimenting.
I chose the Bikila LS because of the three models of FiveFingers I have (Bikila LS, KSO, KSO Trek), it is the most padded, least minimalist shoe. In fact, I wish it were more minimalist, because in the summer, my feet get so hot and sweaty (the ventilation is poor) that I get blisters if I run very fast or long. I speculated that these limitations might be virtues in colder conditions.
On my run today, I had to watch my footing because there were invisible icy spots on the roads. I am unsure of the traction of the Bikila LS shoes in case of ice, I must admit. However, my feet did not feel particularly uncomfortable. To be sure, it was a very short run, and the temperature of 29F was not very low.
When I returned home and took off my shoes, I noticed that my feet were very cold. I’m not sure whether to worry about that. I suspect that on longer runs with lower temperatures, I might have something to worry about, but I have to do more experiments. One option I have is to wear Injinji toe socks, of which I have a couple pairs. I don’t ordinarily wear these socks because they somewhat get in the way and bunch up when I wear them with FiveFingers shoes, but for winter they might be a lesser evil.
Also, for traction, I might want to try running in my KSO Trek, although I have tried to save those just for trail running and hiking.
How about mono-toed shoes?
Even so, it is possible that I will end up investigating a mono-toed minimalist shoe to keep my toes warm. I still don’t own a pair, although I have tried on some New Balance Minimus and Merrell Glove models. I did not like the feel of any of them, although I have not yet encountered the newer New Balance Minimus Zero shoes (to come out in February 2012) that might work better for me than the original Minimus line.