K.P.
Is he in daycare or at home?
At that age, my son lived in elastic waiste sweat pants and long-sleeved t-shirts. Every time JC Penney had a sale... we were there!
Snow suit, boots, hat with covered ears, multiple sets of mittens, socks, socks with the rubber on the bottom for inside, hoodies (2 at least), and jeans.
Just think, warm & layered!