Although Wolff calls Old School a novel, its plot follows the events of his own life beginning with his enrollment at prep school (in other words, it begins where This Boy’s Life leaves off). The narrator of the story, Wolff’s stand-in, is intimidated by the class snobbery at his school, particularly the hint of anti-Semitism that he senses. (The narrator’s father, like Wolff’s, is Jewish.) He struggles with most of the academic material at school, but finds his niche in English classes and on the staff of the literary magazine. He becomes caught up in a school tradition—the chance to have a one-on-one meeting with a famous visiting writer. These writers include Robert Frost, Ayn Rand, and Ernest Hemingway, said to be a friend of the school’s dean. When the time comes to compete for the Hemingway prize, he struggles to produce a worthy submission. In the end, he plagiarizes a story from another school’s literary magazine, changing only a few details. In the story, “School Dance,” a prep-school girl hides her Jewish identity in order to attend a country club party. The narrator’s version of the story (with the protagonist changed to a boy) is initially praised by everyone at school, but before long his deception is uncovered, and he is expelled the same day. His acceptance to Columbia University is withdrawn, and he drifts for a few years before enlisting in the army.
The last section of Old School tells the story of Dean Makepeace, who left his post for a year at the time of the planned Hemingway visit. It turned out that the dean had never, in fact, known Hemingway, but he had allowed this misconception to circulate on campus for many years. When he finds out not only that Hemingway will visit campus, but also that a student is going to be expelled for dishonesty, he impulsively resigns from his position. Although he eventually returns, his decision to separate himself from the false persona he had formerly allowed to stand reflects the novel’s emphasis on the fluid process of identity creation.