Nic - let him go barefoot. If the path or whatever gets too hot, that might be incentive for him to put some shoes on. Barefoot is so much better, and important, for the development of the feet anyway.

btw.. walking heel to toe is the wrong way of walking. Here is some interesting reading that I posted a while ago Preventing children's foot trouble

As for hat.. can't help with that one, Tallon is pretty good with his hat, and actually asks for it if he's going to play outside lol. It doesn't always stay on the entire time, but I must admit he's pretty good with it.