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Well I know you have a son but how about tights if you bought them in plain colours like red or blue and wore them under pants no one would know the difference. Tights keep them very warm.
I heard about a new product today that keeps socks on. It has a fastener around the sock so kids can't pull them off. Do you think that will work?
I haven't heard of this product but it might. Just make sure it doesn't get too tight around the legs as you don't want to stop blood circulation