Holden Caulfield buys a red hunting hat in New York after he loses the fencing equipment in the subway. The hat wasn’t of any great value, just one dollar, but Holden was delighted by this hat.
From this time on Holden wears the hat quite frequently, but every now and then he prefers to take it off, namely when some guy is around he knows(p.61). The hat has a very long peak, and Holden wears it backwards, so the peak aims behind him.On the one hand he wears the hat when he is under pressure, on the other hand he wears it when he wants to fool around. This shows that the hat has two meanings, two tasks.
Also significant is the colour of the hat, which is red, like the hair of Holden’s dead brother Allie. This mirrors the relatedness between Holden and this red huntung hat, since he really adored his little brother (p.38)
I bet you do not often see anyone with a red hunting hat, which again points at Holden’s character: Holden wants be different from other people and so the hat transmits its uniqueness and individuality to Holden and helps to depict him.
At the same time, Holden has more confidence and courage to challenge those, he dislikes and dispites (phonies), when he wears the hat (he always mentions that when he’s wearing the hat).
Now we can go even further and say, that this particular hat represents Holden’s isolation from society and he seems to be a different person when he puts on this hat. A shield is formed to avert the “cold” outside world with that hat and so a big dependency on the hat emerges (p.53, 88).
To summarize, this hat acts like a mask for Holden, he has to rely upon.
Even though the hat has this negative nature, it also may symbolise the more positive value of protection, shelter and cover.
On the one hand the hat protects Holden against the mentioned phonies and adults, but on the other hand it specifically protects the childhood innocence, since he sees himself as the catcher in the rye when he wears this hat (note: symbolism of the catcher in the rye is the attempt to protect the children from falling off the cliff into adulthood).
Durning the story process, Holden becomes more and more attached to his head, but at the end of the novel, Holden starts to loose his need for that hat, because he realises, that he can’t protect every child from becoming an adult, neither can he protect himself nor the hat and he now believes that he should stay at home and face his responsibilities without the help of The Red Hunting Hat.
Finally, Holden donates his hat to his little sister Phoebe (p.180), who stands for that what is not phony, because he thinks, the hat will protect her, since he has no need fot it anymore. With that, Holden emphasises the positive qualities of the hat for which it was originally made.
To conclude, the symbolism of Holden’s Red Hunting Hat assists to show Holden’s progress in maturity and it also helps to characterise his extraordinary behaviour.