What kdw said - a good quality cycling boot will last many seasons. This is not an area you should skimp on if you are planning to enjoy winter cycling. I do a lot of cold fatbiking up here in Quebec and depending on the temps I'll use either my 45N Fasterkatts or my 45N Wolvenhammers. The Fasterkatts can take me from 0 to -10 cel. and the Wolvenahammers from -5 to -20 cel.

I also use backcountry snow pants with suspenders that cover my boots. Warm legs = warm feet.

Edit: Both boots are purchased a little bigger to fit thicker wool socks.

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