My rebby in Chaim Berlin wore a black straw hat in the summer when I was a bochur. And this wasn’t in the 1940s. He is still a rebby, but doesn’t wear the straw hat.
The nothing “wrong” with a straw hat. A lot of the hat issue, color, up/down etc is a symbol of which group you belong to. Today its not yeshivish to wear one so people who care about that for various reasons don’t wear one.
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