Hats...

I think I lost two hats in quick succession about ten years ago and none since. My situation was that my daughter was still in high school and was applying / accepted to a secondary school. So I was about to "lose" my daughter and take on massive debt (more than the home mortgage, in fact). So the folklore meaning fits for me -- both as an omen (debt) and new beginnings (empty nester). And of course distraction, most of all.