Re: teaching toddler to put on outdoor clothes
My kids spend lots of time in outdoor gear since we live in the frozen north. It hasn't gone below zero yet but it's been very very close the past few mornings (+3*F this morning!).
They don't use snowsuits or puffy coats in the car because of the safety risk.
DS is 3 and knows how to put his snowsuit or snow bibs and coat on. His preschool has 20 3-5 year olds to get dressed and they go out at least twice a day, so they need to learn how to get dressed on their own. The easiest way is to teach them how to unzip their snowsuit and lay it on the floor, and then lie down, slide legs and arms in, stand up and zip. Hats and boots are easy. Gloves generally need some help.
My DD2 is in Kindy and they spend an hour outside every morning. They are all expected to get themselves dressed except for stuff like zippers and tucking their gloves into their sleeves. She wears snow bibs and a down jacket over it, and can do it now after a bit of frustration with the zipper.