I had a pair of boots I bought on a BOGO sale at Payless a few years back. They were cute, but really did not keep me warm, which I quickly discovered after trying to shoot in 15F weather for an hour at a time! I insisted to C that I needed to find some boots, but I didn't want to order any online without trying them on. So, we went out to the local sports store, which has outrageous prices, but they were selling boots for 20% off. I got a pair of Columbia ones for $72 plus tax!
Since then, I have been incredibly impressed. They are supposed to stay warm until -25F. I have been using them as cold as 10F and they have been wonderful. I haven't had cold feet since.
My next task is to find warm enough gloves. I do the layer thing, but nothing seems to keep me warm enough for long enough, even at 30F. Any suggestions?