1. put his hat in a shopping bag and hang it on the handles, and he can wear his jacket or fold it and put it in the bag also.
2. my 2 year old rides a tricycle, and although it was hard to find one that fit, even SHE wears a helmet. my 4 year old still has the training wheels on, and he wont go on without a helmet (on his own he will say something, but i guess it is because he knows i wont let, so it is ingrained in him)