Holden Caulfield is an unconventional teenager with many conflicts. He failed out of four boarding schools. He has also been visited by a psychoanalyst. These obstacles prevented him from effectively communicating and connecting with others. His judgmental mentality and inability to communicate has caused him to place anyone that acts conventional into a prejudice of "phonies ". His creation of phony prejudices were also caused by his refusal to move on from a child-like state of mind and mature into a "conventional " adult. As a result of all these issues, Holden defines the people around him according to how he views them and not according to how society views them. Thus, he alienates himself from the "phony " society these people comprise of, and falls into a cycle of harshly judging others while wandering around aimlessly without reason. .
Holden has many personal issues with conventional people so he alienates and judges them according to his standards of how phony they are. The way they act, the way they look; it all bothers him. He expresses his hate for conventionalism in many ways, but there is one very unique way. He wears his red hunting hat. Now, his hat is no ordinary hunting hat. It "is a people shooting hat " (Salinger 30), and "[he] [shoots] people in [that] hat " (Salinger 30). Holden does not actually wear his hat to go and shoot people in, but rather he wears it to "shoot " them down with his degrading judgmental attitude. It is also very clear that Holden doesn't just use his hat as a "people shooter ". He uses it as a symbol of his own uniqueness and individualism. Holden believes that the world does not deserve any praise from him because it is so conventional. As a result, he wears his hat and continues to grow his acridity towards anyone he labels a phony (which happens to be a lot of people). .
Holden only has security in what doesn't change and fears whatever he cannot control.