Being one of those who live in the Great White North, I fly year round - as do many others. My hands don't take cold all that well, but I have a cheap solution. I use the $2 cotton gardening gloves - they cut down the wind and cold enough for a few minutes of flying, yet do not impede the feel of the sticks. Other than that, just dress as if you are going out to watch some kind of a winter event. Don't make a big deal of it all, enjoy the winter! The less you worry about it, the better.

I fly in conditions down to, say, 10F, normally and sometimes with some lightly blowing snow. IF you can't see your airplane, it's probably getting near time to give it up and go for beers. Our club has a hut with a wood stove. Winter flying is great! If it weren't for the turkey awaiting my imminent attack, I would be out today.

Skis on planes are great, floats are even better for a wide variety of conditions.