Holden Caulfield is an intelligent but insecure high-school junior who is expelled from Pencey Prep which is the fourth boarding school he has attended for failing four out of five subjects. Although Holden seems likable and has a good sense of humour, he has difficulty facing reality, in particular his inability to adjust to his peers and society in general.
Caulfield is immature and refuses to grow and doesn’t like to moved on. He wears the red hunting hat is certainly a peculiarity at Pencey Prep and in New York City. And that is precisely what Holden himself wants to be, different and unique. In short, the hat is his red badge of individuality. Holden's hat could also symbolize his own personal hunting expedition