I have two pairs- shimano shoes with MTB clips which I got when I first started riding. I wear these with wool socks as my "winter" shoes when it is rainy and cold if it ever is that in a combination that I might be riding in. Keep in mind that I ride outside of Houston so oue winter is pretty non winter most of the time.

My main pair are keene sandalswith mtb clips which I wear with wool socks if it is cold or cool and with regular socks the rest of the time.

I have rain coversetc. but I have rarely used them, the shimanos keep my feet basically dry and the wool socks insulate my feet sufficiently for this area.