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Holden responds that
This is a people-shooting hat ... I shoot people in this hat' (Chapter 3).
This reply shows that Holden is clowning around, as he does quite often in the book - he is already wearing the hat the wrong way round, quite deliberately. However, this response maybe also hints at his pervasive sense of alienation from other people, his general inability to get on with his peers and older adults (although he enjoys the company of children, like his sister Phoebe).
In this chapter Holden is being persistently annoyed by Ackley, the student next door who has barged into his room and keeps on disturbing him when he is trying to read. Being unable to get rid of him, Holden resorts to kidding around.
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