I had this issue with my 4 year old last winter. I'm going to get my ass chewed out on here, but I called CAS. I explained the issue to a lady, and she was lovely about it. She actually took the time to come to my home, and explain to my daughter that if she is outside with out being properly dressed, I and her daddy could get into very very big trouble.
This was after trying 5 different hats, different jackets, boot, snow pants ect. And not only us having problems bu the school. It was insane!!!!!
She explained that I had said I was going to take her shopping that evening, and that she had to make a choice about what she would wear based on my selection. The lady also said that if she were to stop by school, and m were not wearing her winter wear, that they would have to have another discussion.
I was so impressed and touched that she took time to help make something so difficult into something that now take no time and struggle.
M does have to tuck he pants into socks before putting in snow pants, and boots, and she has to hold her longsleeved shirts to have them not bunch up.