Originally Posted by Notso_fastLane

One of the most notable items in your wardrobe that is conductive are you bike shoes. If you don't have insulated, winter specific shoes (or very good insoles), most bike shoes are simply hard plastic with a metal cleat. That metal cleat is in direct contact with your pedals. That is essentially a significant, and pretty efficient, conductive heat sink (metal is something like 10-50 times more efficient at conducting heat than plastic/air). The best insulation generally needs to be between your foot and the sole of the shoe, although covers help as well, since they reduce the convective losses for the rest of the shoe.