Maybe try some of the soft-soled leather slippers that are OK for light outdoor use? I've had robeez for all my girls, and loved them. They might be a good "in-between" sort of thing to ease him into wearing the dreaded shoes! I can imagine that after running around free and bare for as long as he can remember, shoes feel pretty lousy. Robeez are really soft and flexible, but offer a little more protection than just socks! (you can get them on e-bay.)
Otherwise, I've seen here shoes called "Little Squeaky Feet." They are shoes for little one that have a squeaker in the heel, which kids get a kick out of, and it teaches them to walk properly (rolling from heel to toe.) The squeaker is removeable for when he is used to the shoes, or when it is driving you crazy.They are also fairly soft and flexible, but definitely a shoe, not a slipper.
One other thing he might like is the shoes that have the little flashing light in the heel that light up when you take a step. I'm assuming they sell those in Australia - they're all over here. That might be enough of a thrill/distraction that he'll keep them on.
As far as the hat goes, I have no help. Sorry. My kids won't wear theirs either.![]()




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They are also fairly soft and flexible, but definitely a shoe, not a slipper.

i tell ya he is stubborn
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