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Mona Lisa Smile tells the story of Katherine Ann Watson (played by Julia Roberts), a feminist teacher who studied at UCLA graduate school and left as a first-year teacher from "Oakland State" University (thought to be a fictionalized University of California, Berkeley), leaves her boyfriend behind in Los Angeles, California in 1953, to teach at Wellesley College, a conservative women's private liberal arts college in Massachusetts, United States.

Watson tries to open her students' minds to their freedom to do whatever they want with their lives. She encourages her students to believe in themselves, to study to become career professionals, and to improve their economic futures. She uses her modern art teachings as a vehicle to put across her opinion to the young women that her students need not conform to stereotypes of women made by society. She felt that Modern art was a questioning of the status quo and could be used as an eye-opener for her students that were confused about their role in 1950's society, even introducing the students to the work of Jackson Pollock a member of the art avant garde at the time. She feels that women could do more things in life than solely adopt the roles of wives and mothers. In one scene of the movie, she shows her students four newspaper ads, and asks them to question what the future will think of the idea that women are born into the roles of wives and mothers.

Watson's ideas and ways of teaching are contrary to methods deemed acceptable by the school's directors, conservative women who believe firmly that Watson should not use her class to express her points of views or befriend students, and should stick only to teaching art. Watson is warned that she could lose her job if she continues to interact with students as she has been doing.

Undaunted, Watson becomes stronger in her speeches about feminism and the future of women. She is a firm believer that the outlook of women in society needed to be changed if women were to achieve better futures, and that she needs to instill a spirit of change among her students.

Watson eventually breaks things off with her boyfriend, Paul Moore (John Slattery), after a disastrous wedding proposal during a visit of his from California. She eventually starts a relationship with Italian teacher Bill Dunbar (Dominic West). Although the relationship is frowned upon by the faculty at Wellesley College, due to inter-office romances being discouraged, the two continue seeing each other. However, Watson ends the relationship after finding out that West lied about his military service as he did not serve in Europe during World War II, but was rather stationed in America.

The film also focuses on the lives of various students of Watson's, chief among them: Elizabeth "Betty" Warren (Jones) (Kirsten Dunst), a rich girl with a conservative, domineering mother (who, as head of the Alumni Association, exerts significant power and influence at Wellesley) who marries a man who is unfaithful to her, and also clashes constantly with Watson's teaching style; Constance "Connie" Baker (Ginnifer Goodwin), who has insecurities about her body while searching for a boyfriend; Giselle Levy (Maggie Gyllenhaal), one of the few Jewish students at Wellesley at the time, who has affairs with teachers - including, at one point, with Bill Dunbar - and older married men, but who is also one of the first student to admire Watson; and Joan Brandwyn (Donegal) (Julia Stiles), who is initially conflicted about whether to pursue law school after graduation or become a housewife to eventual husband Tommy Donegal (Topher Grace).

Although many of the students are initially put off by Watson's style, as the film progresses, more and more begin to come around and in many cases admire her. Even Betty comes around at the end of movie, despite being her most vocal and vehement critic.

Watson chooses to leave after the one year, but, as she is leaving the campus for the last time, her students run after her car, to show their affection and to thank her for her lessons. The entire departure scene is narrated by Betty who dedicates her last editorial to Watson, explicitly stating that Watson is "an extraordinary woman" and an individual who "seeks truth beyond tradition, beyond definition, beyond the image." The film ends as Betty desperately struggles to keep up with Watson's taxi as it speeds up, thereby portraying her admiration and respect for Watson.