I have had this issue too, so we just started wearing our hats inside too. I do it earlier in the morning, before we go out and get all wet/dirty, and make a game out of it. It's like "dress up" and because I am usually strict about wearing outside clothes in the house, they think it's fun to break the rules. I have also found that this kind of activity helps with the "self-help" skills, for playtime rather than in a hurry, when we're all getting dressed to go out.
As far as keeping the clothes on, I think the best lesson is the logical consequence, being cold/uncomfortable. It takes some kids longer to learn this lesson than others, unfortunately. We've had snow the last couple of days and several times, the toddler kept pulling his mitts off. But I won't put them back on him until he is uncomfortable and cranky because his fingers are cold. Hopefully he'll learn while it's only -1 and not be doing it when it's -20.


































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