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The hat is most likely a testament to his dead brother Alie and his little sister Phoebe: both with red hair.The hat represents Holden's emotional vulnerability.
I put on this hat that I’d bought in New York that morning. It was this red hunting hat, with one of those very, very long peaks. I saw it in the window of this sports store when we got out of the subway, just after I noticed I'd lost all the goddam foils. It only cost me a buck. The way I wore it, I swung the old peak way around to the back—very corny, I'll admit, but I liked it that way. I looked good in it that way.