Thanks everyone for sharing thoughts...
Just to update: When I picked up DS from daycare on Friday, he was still wearing his shoes! They said that he must have just forgotten that they were on. He seemed to be walking better in them. We haven't had a major meltdown over shoes since Friday morning. I'll call this my Christmas miracle.
I understand the point that a couple of folks made about letting children walk barefoot until absolutely necessary. In fact, I even tend to agree with that theory. That was my reasoning behind going to buy Stride Rite brand shoes as they are supposed to be designed to mimic barefoot walking. Otherwise there is no way that I could pay $40 for a pair of shoes I know he'll out grow in a few months.
I'm afraid we are long overdue shoes being a necessity. We live in the southeast and tend to have some exceptionally mild winter days throughout the entire season. The daycare DS attends is required by the state to give children 45 minutes of outside play time a day when the weather is within certain limitations (this week for instance our highs are in the 60s). DS loves to play outside and cruise along the fence. But even in great winter weather, socks were just not enough protection for his little feet. The grass in shady spots almost never fully dries out during the winter so his feet would get wet. It seemed preferable to put on shoes than to go with wet feet or miss his outside play time.
It didn't seem fair to ask the daycare workers to fight this battle with him on a day-to-day basis. So, we just opted to wear shoes throughout the day. It's probably safer considering the fact that he's in a room with kids as old as 3. Little ones might not always watch where they are headed and might step on his little toes once he really starts walking. Added protection on the top of the foot I'll call a bonus. For the record, we still go barefoot at home as much as possible.
Thanks again for the input. It's always helpful to hear what other mommies think.