I.S.
They make sleepNplay outfits up to 4T in thinner cotton... for the winter you might consider using one as an undergarment so at least he can't pull off the footies... it may look a little strange as far as fashion goes but it'll keep the wind from blowing up his pant legs. Then put the shoes on over the footies... after a few failed attempts at producing bare feet on his own he may even start to leave the shoes alone...then you can get the ones that tie and the little "locks" for the laces... good luck!
Stef:)
MaMa to 12mo Nico and 3.5yr I.