I like cotton ankle socks with wool/wool blend over socks in the winter. I wear heavy 100% wool hiking socks on very cold winter days. And what was mentioned above, insulating innersoles -- Thinsulate being the best. I like the cushion gel type.
Also, inside the floor surface has a lot to so with cold feet. Concrete slab foundations are the coldest: Put a heavy rug under your feet. Old houses with floor drafts will make your feet feel cold. Wear pac-boots outside in the snow or in the very cold.
If you want a 'shiny leather compromise' --
https://www.ghbass.com/product/samue...gclsrc=a w.ds I have a pair of these for winter and air travel (they slip off in the security line) clunky looking and not "high fashion" -- warm and comfortable -- practical.