It's definitely possible to over-insulate your feet...to a point where you're literally insulating them from the overall warmth inside the rest of the TQ that your body is heating well.
Feet suck in general at generating heat. So to expect them to warm themselves inside their own little "sleeping bags" usually doesn't work.
I like a medium wool sock and maybe my Enlightened Equipment booties over the top if necessary. Those Dutchware booties look really nice too.
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