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K.I.S.S.
How about the Keep It Simple Sweety approach. Snowpants and boots sound like a nightmare combo. And he has to take them off and back on at school. I'm tired thinking of it.
Maybe ask youself...does he really need all this? You aren't a bad Mom if you kids pant bottom get alittle wet. Maybe just the boots would be easier. My son figured out early how to take his shoes on and off without ever untying them, but where they still stay on. Works for both of us.
Make sure that his lunch has lots of protein to hold him for the afternoon, and some carbs to help keep his energy up to go back. Maybe taking him out to lunch (something simple like grilled ham & cheese at a diner counter). If he likes it, you could use that as an incentive. "If you get ready nice today, we can go out tomorrow."
Just some ideas. Good Luck!
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