Auchincloss wrote about 70 books, the best known of which was The Rector of Justin (1964), a tale of the founding headmaster of an exclusive New England prep school. It was a world with which Auchincloss was intimately familiar, as a graduate of the Groton School in Massachusetts. The book has been called a minor masterpiece of 20th century literature.
Auchincloss was born in Long Island to a privileged family and grew up on the Upper East Side of Manhattan. He always claimed that there was no Auchincloss fortune. "Each generation of Auchincloss men either made or married its own money," he wrote. He did what was expected of him, studying at Yale and taking a law degree from the University of Virginia, as his father had done, similarly, before him. He loathed law, and was more inclined toward artistic pursuits like his mother.
Auchincloss worked for a Wall Street law firm for 32 years and was successful at it, limiting his writing to weekends. He tried once, in the early 1950s, to write full time, but went back to a law firm because he was feeling disconnected from "the real world." His law career is made evident, through reference, in much of his work.
Auchincloss' career spanned 70 years and his work reflected his privileged background in the northeast establishment. The Embezzler (1966) examines the life of a Wall Street stockbroker who gives in to opportunity to steal during the Great Depression.
He tells the stories of multiple generations of upper crust families in such works as The House of Five Talents (1960), Portrait in Brownstone (1962), and East Side Story (2004). His last book was Last of the Old Guard (2008).
Most prestigious book awards eluded him, but he did receive the National Medal of Arts in 2005. He was elected to American Academy of Arts and Letters in 1965.