I would skip the shoes because Toby will end up wearing them all the time, forever.
He has to overcome his fear or dislike of the flooring.
Max has a thing for cement. We walk in the street, so he doesn't have much experience with sidewalks. Also, I trained him never to go in the garage, which has a cement floor. I'm trying to re-train him to walk with me through the garage now that I have 2 boys and it is easier to enter/exit the house that way. You should see him on the garage floor. It's like I'm asking him to walk across hot coals. He isn't much better on sidewalks, but we are working on it.
Cesar Milan worked with a Great Dane who was afraid of shiny floors after taking a nasty spill on one. He took the dog out running and then ran back in the house toward the shiny kitchen floor. The dog balked many times and pulled Cesar down. Eventually the dog ran straight into the kitchen before he remembered the floor. Once there, he froze for a moment, but then walked around normally.