I rather doubt that folks will be whispering behind their hands ….. “Oh dear, look at that chap over there, he’s wearing flat shoes and a fedora. Perhaps someone will take the poor fellow aside and help him.“
Wear your hat with whichever shoes you wish, and wear whichever shoes you choose with...
My Akubra (Territory) is my everyday and all-occasion hat. Superb sun protection.
I have other hats, but it is the one I wear every time I leave my apartment.
I wish that I had discovered Akubras sooner.
Your hat, and your head.
As others have said, if it doesn’t fall off when you bend over, you are good.
I chose to wear mine lower, so I don’t need as many thumbtacks on windy days.
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