That is one of my biggest frustrations...when parents don't dress their kids for the waether! Part of it is because parents spend their days inside most of the time and are not in touch with how cold it can be to actually spend an hour or two outside playing. They don't bother to check forecasts either. I have had to put pink hats etc on boys many a time as I refuse to take them out in the cold hatless. Could you let him ride in the stroller and wrap a blanket around him?