I have an 8 year old dcg that gives her parents attitude about wearing her outdoor clothing, they let her leave at pick up without even wearing a coat when it is -20 if she whines about it. But for me I don't give the option and she wears full winter wear always when we go outside. I taught 8 and 9 year olds for a few years and many of them will try to pull not dressing properly, but I never let it slide - they are still young children that enjoy active play outside and they need to dress for it.

But it is part of my contract agreement that they have full winter wear, though this girl is always forgetting stuff at school. She definitely seems to have the responsibility put on her to having all the appropriate winter gear in her bag. We always have outdoor playtime after we pick her up off the bus, and if she isn't dressed properly she has to just sit and watch the fun - with a reminder from me of "I guess next time you'll wear your mitts!" I think this has an effect on her, she seems to have gotten the hint.

I would bring it up face to face to the parents, mentioning how he was so cold because he wasn't dressed for the weather and how it affects your ability to run your program properly. I'm sure his teachers at school feel the same frustration of having him come not properly dressed.

I think older dck's are hard in this aspect, they are gaining responsibility for self care, which is a good thing, but they don't always make the best choices.