I wear LL Bean Snow Sneakers. I'm going on my sixth winter with them. I wear those when daytime temps maintain at 42f or below. They have superior Primaloft insulation, which thru my own experimentation blows away Thinsulate in sub freezing temps. And no wonder, I looked it up. Primaloft has twice the R value of Thinsulate. These, along with a good thick wool sock(or two) keep my feet warm down to about 5f-10f. Anything lower, then I wear NEOS overshoes, which the snow sneakers fit inside good. You can spend whatever you want on shoes. But in my mind, a good winter hiking boot will beat out a high priced winter cycling shoe. There are lots of riders here who swear by Lakes, and 45north, etc. But you don't get too many who say how those protect their feet when its 20 degrees out. Having your toes so cold that they feel like they might snap off is not fun.