Extreme(ity) Cold

My toes are damaged. I rode in the cold one too many times without the proper shoes/protection from cold and wet....

Now I suffer from 'chilblains' a medical term used to describe the condition brought on when the toes are really cold and are warmed up too quickly. This results in the tiny capillaries bursting. The blood has nowhere to go so it pools just under the skin surface, and feels uncomfortable. The toes look bruised red, blue, and blackish. It's not something you want to have happen to your toes(or fingers). Under 45F I will feel it again if I don't take the proper care of my toes, and then I'm fighting it all winter....

Here are some of my observations/theories/remedies in my personal quest to keep my toes warm.

I have a pair of SealSkinz socks--neoprene--combined with very thin poly first layer, my toes stay warm and dry. The funny thing is they do feel moist, but not uncomfortable. So far it works down to about 20F, even when my boots get wet or leak.... The other thing that works in drier conditions ( not when my boot leaks) is charcoal toe warmers, in between the (same)first layer and wool socks. You need to wear a shoe size larger than normal, otherwise, neither will work.
I have yet to really test in colder than 20F

With clipless pedals, there's the problem of the metal cleat and plate right under your feet that conducts the cold....the only real way around that is to commit to flats for winter. I've never been able to do that, but I suppose in deep snow it would make sense anyways. The one major thing that I learned is that your body(core) has to be warm. I used to think that it was OK to feel a little chilly in the parking lot, before the ride. My toes/hands would never warm up 'cause your body needs to keep itself warm. But if your core is warm to start, your extremeties will get more blood right away and if you get too hot, you can strip off a layer. I now find that I can even take my gloves off once I get going(hiking not biking). My toes now get so much circulation that I still get a a mild 'chilblain effect' --that is, the extra blood pools in the damaged areas at the ends of my affected toes and results in some of that uncomfortable feeling I associate with chilblains, but the symptoms seem to resolve much quicker.