Originally Posted by
kiltedcelt
Feet are a problem though. If I keep riding clipless I can only fit a thin pair of wicking socks under some Wigwam Merino wool socks, all crammed into my cycling shoes with some neoprene booties over the outside. My feet can get cold even on days in the higher teens or even low 20s, let alone single digits or minus single digits. My booties are falling apart mainly because of poor design (the fronts don't stay tight over the toes and start peeling up). I was thinking of getting new booties from Pearl Izumi and maybe when it's down in the single digits I could still wear the crappy booties over the PI booties for an extra layer of insulation.
Booties, even multiple pairs, is not the solution. The don't trap additional air inside the shoe. This is what keeps your feet warm. Booties also don't provide any insulation to the bottom of the shoe, and there remains the matter of the cleat sucking heat out of your foot.
Winter cycling boots solve the matter. My Lake MXZ302s have in insulated outsole, and come with insulated insoles. The cleat backing plate also does not penetrate the outsole. This is in addition to the full grain leather uppers and the insulation. The downside is that the Lakes have become hard to get this year. There are several other makers with winter cycling boots. They're certainly worth investigating. And remember to buy a (metric) size or two larger to accommodate thicker socks and more air space.
As for the rest, you have a couple of good workable alternatives. You'll get there. And don't forget the cyclist's secret weapon for keeping warm: Pedal harder!