Holden is a well-heeled young man, which means he comes from a wealthy family, so he goes to New York City well equipped with money. He had previously purchased his signature peaked red hunting cap there, which he wears backward on his head. While journeying through the city after leaving Pencey, he buys other items.
He, for example, purchases drinks for three people he meets in a bar: Laverne, Bernice, and Marty. He buys the services of a prostitute for five dollars, though he only talks to her. She tries to charge him ten dollars, but he won't pay that much. He buys a newspaper and tickets to a theater performance called I Know My Love. He buys a pad and a pencil in a stationary store with the idea he will pretend to be a deaf mute. He buys Phoebe a carousel ticket. He buys movie tickets and pays for ice skating.
With his hotel room, meals, taxis, the ten dollars he gives the nuns, and other expenses, Holden spends upwards of a thousand dollars in today's money on his New York spree.
Holden has been forced to return early to school from New York because he managed to lose the Pencey Prep fencing team's equipment on the subway. Unsurprisingly, the other members of the team are angry and annoyed at Holden and ostracize him during the rest of their trip to the city.
But the trip's not a total dead loss for Holden. Before heading back to Pennsylvania, he takes the opportunity to do a bit of shopping, and he treats himself to a red hunting hat with very long peaks. Holden is rather pleased with his purchase. Not only did the hat cost him only a dollar, it also makes him stand out from the crowd, especially when he wears it backwards. The red hat will come to be a very important symbol in the story for Holden's individuality. But for now, although it looks kind of corny, at least it doesn't make Holden look like a phony, and that's what matters.
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