Hats in Literature: A few examples

Dunsany - The King of Elfland's Daughter

"They listened spellbound to the ways of men; and every now and then, as when he told of hats, there ran through the forest a wave of laughter."

Tolkien - The Fellowship of the Ring

"Presently Sam appeared, trotting quickly and breathing hard; his heavy pack was hoisted high on his shoulders, and he had put on his head a tall shapeless felt bag, which he called a hat."

* * * 

"There was another burst of song, and then suddenly, hopping and dancing along the path, there appeared above the reeds an old battered hat with a tall crown and a long blue feather stuck in the band."

* * * 

"So [Tom Bombadil] sang, running fast, tossing up his hat and catching it, until he was hidden by a fold of the ground: but for some time his hey now! hoy now! came floating back down the wind, which had shifted round towards the south."

* * * 

"[The hobbits] begged [Tom Bombadil] to come at least as far as the inn and drink once more with them; but he laughed and refused, saying:

Tom's country ends here: he will not pass the borders.
Tom has his house to mind, and Goldberry is waiting!

Then he turned, tossed up his hat, leaped on Lumpkin's back, and rode up over the bank and away singing into the dusk."

* * * 

"Arrows fell among them.  One struck Frodo and sprang back.  Another pierced Gandalf's hat and stuck there like a black feather."

Chesterton - "On Running After One's Hat"

"[T]here is a current impression that it is unpleasant to have to run after one's hat. Why should it be unpleasant to the well-ordered and pious mind? Not merely because it is running, and running exhausts one. The same people run much faster in games and sports. The same people run much more eagerly after an uninteresting little leather ball than they will after a nice silk hat. There is an idea that it is humiliating to run after one's hat; and when people say it is humiliating they mean that it is comic. It certainly is comic; but man is a very comic creature, and most of the things he does are comic [...]. And the most comic things of all are exactly the things that are most worth doing [...].

Now a man could, if he felt rightly in the matter, run after his hat with the manliest ardour and the most sacred joy. He might regard himself as a jolly huntsman pursuing a wild animal, for certainly no animal could be wilder. In fact, I am inclined to believe that hat-hunting on windy days will be the sport of the upper classes in the future. There will be a meet of ladies and gentlemen on some high ground on a gusty morning. They will be told that the professional attendants have started a hat in such-and-such a thicket, or whatever be the technical term. Notice that this employment will in the fullest degree combine sport with humanitarianism. The hunters would feel that they were not inflicting pain. Nay, they would feel that they were inflicting pleasure, rich, almost riotous pleasure, upon the people who were looking on. When last I saw an old gentleman running after his hat in Hyde Park, I told him that a heart so benevolent as his ought to be filled with peace and thanks at the thought of how much unaffected pleasure his every gesture and bodily attitude were at that moment giving to the crowd."

Lewis - The  Magician's Nephew

"'Womfle - pomf - shomf,' came Uncle Andrew's voice from inside the hat.

'None of that now,' said the policeman sternly.  'You'll find this is no laughing matter.  Take that 'at off, see?'

This was more easily said than done.  But after Uncle Andrew had struggled in vain with the hat for some time, two other policemen seized it by the brim and forced it off."

(Note: The hat in question just happens to be Uncle Andrew's "best tall hat" which he'd polished up to impress Jadis.)