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Mildly related but I was a grown ass man when I learned the striped shirt boy isn't meant to be Jughead from Archie, but the crown was an actual fashion trend during the 30's.
It was?? Where'd it even spawn from? It seems that childrens' fashion usually reflects grown-ups' fashion but with less uniformity, are the crowns perhaps inspired by some kind of entertainment figure?
They're called whoopee caps and the story I was always told was they were made from fedoras that had their brims cut into the crown pattern. My grandpa had one from when he was a kid.
They were also associated with mechanics.
Ah, that explains why they have that look. It's always interesting to see how people manage to turn a thing (fedora) into something new by just modifying it slighty. You don't see hats around as much nowadays anymore too, crazy to think of how common they were before cars took over.
I think at first it was practicality. Everyone wore a fedora all the time, but people in mechanical trades would invert them then cut off the brim so it didn't get caught in machinery. Then kids started imitating the types of hats their dads were wearing.