Leave room in the cycling SHOES; 1 to 1.5 sizes larger than summer shoes. Wear medium weight wool socks and you will be warm in most weather. DON'T tie them tightly. The trapped air space is heated air. It makes you feel warm. In extreme wind use waterproof shoe covers. Or go the MTB high top shoes. In Misery ; 15 mph wind @ 15 mph speed in 10* F with high humidity makes you feel the cold. Then add sleet or snow.