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My kids hated cold (being outside in winter) up to 3 years old. After that age they started to connect in their minds what hats, scarves, mittens are for, and got better grasp on keeping their mittens on during playing. Before 3, they would pull anything off their hands, thinking that they need hands to play. Cold snow (or just cold wind) would make their hands cold in 5 minutes, they'd start crying, and putting mittens back on their wet cold hands - it was just a mess. At 3, my daughter learned a little rhyme "shirt-sweater-jacket", that helped her to remember to put on 3 layers.
Basically, they were home-bound a lot in winter until they were 3.

I have several warm hats that tie under the chin for my son. He tries to pull them off at first and gets frustrated, but I just distract him with something and then he leaves it on and forgets about it. I also cut up tube socks and sewed the tube part to his gloves so that they reach up to his shoulders (over his sleewes) and he can't pull them off.

That is a great idea!