Posting here instead of toddlers because I suspect the usual advice would be, "let the child figure out how much clothing to wear." I used to think that too, but now I am not so sure. I figured maybe people here would have more experience with this since that is kind of a waldorfy thing?
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I used to not make a big deal about what DD2yo wanted to wear, and I still don't. However, she has had a perma-sniffle since the winter, which I recently discovered goes completely away if she is wearing enough clothes - socks, long pants, and up to two shirts. A hat too, if it's really chilly. If she is busy running around, she will usually keep everything on. But hanging out at home, waking up in the morning, etc... she just takes everything off. And her skin is ice cold, and she is extremely lean. So I'm totally convinced she needs to layer up and stay warm. We've started talking about how it's good to wear socks, and I wear socks with her, but any other tips would be good. She just learned how to take off and put on her clothes, so I am sure that is part of it.Â
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I knitted her some vests but she's really not interested....







