Her first novel, Prep, which took her three years to write, was published in 2005 and concerns a girl, Lee Fiora, from South Bend, Indiana, who goes to Ault School, an elite boarding school near Boston, Massachusetts.
Elissa Schappell, who wrote in the New York Times Review of Books: "Sittenfeld's dialogue is so convincing that one wonders if she didn't wear a wire under her hockey kilt." The New York Times named Prep one of their top five works of fiction for 2005. Entertainment Weekly labelled Prep a "cult-classic" in a 2018 reassessment.
The Man of My Dreams
Sittenfeld's second novel, called The Man of My Dreams, was published in May 2006 by Random House. It follows a girl named Hannah from the end of her 8th grade year through her college years at Tufts and into her late twenties.
Sittenfeld's third novel, called American Wife (2008), is the tale of Alice Blackwell, a fictional character who shares many similarities with former First Lady Laura Bush. In November 2011, it was announced that Red Crown Productions had begun work on a film version, with the adaptation written by Academy Award-nominated screenwriter Ron Nyswaner.
Sisterland was published on June 25, 2013. The book's protagonist Kate is an identical twin with psychic powers.
Eligible was published on April 19, 2016 by Random House. It is a modern retelling of Pride and Prejudice set in Cincinnati, Ohio. In September 2017, ABC announced its commitment to make a TV pilot of Eligible with Sherri Cooper and Jennifer Levin to write it.
You Think It, I'll Say It
You Think It, I'll Say It is a collection of Sittenfeld's stories that Random House published on 24 April 2018.
Rodham is an alternate history political novel about the life of Hillary Clinton, published in 2020. The novel diverges from reality at the point where Hillary chooses not to marry Bill Clinton and enters political life as a single woman.