Both! St. John Regis is a seventeenth century French saint (a Jesuit). Also, the St. Regis hotel in NY is a famous historic hotel. I don't know for sure which one the hat is named after but something tells me it's a reference to the hotel :)
Just my two copper coins: I know a lot of guys who are historical reenactors and they own and wear such garb for the sake of preserving and honoring history, even though most if not all of them have never had real service experience. I would assume PathFinder's motivation is on the same lines as...
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