Not a dumb question at all!!! My girls wear flannel nighties in the winter and have at least those on when going outside to potty before bed (if they get up at night) and first thing in the morning. We keep the house fairly cool, so they always have a sweater or dress on during the winter days. I keep the coats by the backdoor and when it gets really cold, those go on as well every time they go out to potty.
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