Hobbits and hats

this time around, Frodo's thought of leaving like Bilbo without even his hat jumped out at me. That is the detail of Frodo having a hat. I guess in the back of my mind I know hobbits wear hats (certainly the shirrifs do), but I never pictured Frodo in a hat. I am now left to wonder what kind of hat? For what occasions? Does he have several different hats, like a fancy hat? For the first time, I'm thinking about John Q. Proudfoot in jaunty chapeaus!

Apart from the aforementioned shirrifs and a certain wizard in The Two Towers, Gandalf is the only character I can think of who wears a hat. Elsewhere in Middle-Earth we see hoods, crown, helms and circlets, but I can think of only hobbits and Gandalf in hats. I associate hoods with travel (and wandering characters like Dwarves and Nazgul), so it is very interesting that the Grey Pilgrim wears a hat, not a hood. Might the fact Gandalf wears a hat be another subtle sign of his connection to or affinity for hobbit culture?
 
Further data: When the company leaves Hobbiton, Sam "had put on his head a tall shapeless felt bag, which he called a hat".
 
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