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With DS I would either keep him in footy pjs or put the elastic part over the socks. They would still manage to wiggle off somehow though. Now that he's 2 I can never keep socks on the kid, which sucks because it's cold and we have hardwood floors.
I pull his pants over his socks and that usually keeps them on. I am always scared he will lose my favorite carters socks so when we are out I tell my husband to watch for falling socks and I'm constantly checking to make sure they're still on