Holden Caulfield has just returned from a fencing meet in New York City, which was a disaster. Holden, the fencing team manager has left all the equipment on the subway and the team never make it to the tournament. We also learn that Holden has been kicked out of Pencey for failing in four subjects.
This is the third private school Holden has attended. Pencey is, according to Holden, full of phonies.
Holden buys a red hunting hat in New York for a dollar after he loses the school’s fencing equipment. The hat has a very long peak, and Holden wears it backwards, with the peak turned to the back. He puts this hat on when he is under a lot of stress, almost as if the hat can protect him and ends up giving it to his sister Phoebe near the end of the story.
It is also worth noting that "red" signifies danger. Holden's mind is in a perilous state, he is on the verge of a breakdown. The colour of the hat flags this for us. Similarly, the hunting theme associated with it contain elements of danger, Holden feels that there is something from which he must escape, just as if something were hunting him.
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