M.P.
I don't think Toms are really designed well enough to be used in the way you are-every single day. I only wear mine occasionally and they are in great shape. I can see where they would not be though if I were to wear them all the time because they are actually pretty flimsy. I suggest wearing something else-try the Sperry deck shoes. I am amazed at how comfortable mine are and wll made. They have a lot of styles with "character" also.
Oh-and no sox with toms :)