Maggie (Cameron Diaz) and Rose Feller (Toni Collette) are sisters with nothing in common but their shoe size. They were raised by their father Michael (Ken Howard) and stepmother (Candice Azzara) after their mother Caroline died in a car accident. Rose is the eldest; an ostensibly plain and serious lawyer who is protective of Maggie despite her flaws. Maggie is a free spirit who is unable to hold a steady job (due to her virtual inability to read) and turns to alcohol and men for emotional and financial support. Rose grudgingly allows Maggie to move in with her in her Rittenhouse Square apartment in Philadelphia when their stepmother throws her out of the house. Their already difficult relationship ends when Rose catches Maggie in bed with Jim (Richard Burgi), her boyfriend. Maggie subsequently disappears from Rose's life.
A few days before, while secretly looking through her father's desk for money, Maggie discovered a bundle of old greeting cards containing cash. She was astonished to discover that the cards were addressed to both her and Rose and were from their grandmother Ella (Shirley MacLaine). Now, homeless and without job prospects, Maggie travels to Florida to find her and hopefully a new source of income.
When Ella first hears from Maggie, she invites her to stay in her home. She admits to her close friend Ethel how Caroline was bipolar, and sent Ella a note several days before her death to look after her girls. So she lets Maggie stay with her partially out of guilt for abandoning her responsibilities as a grandmother. However, as time passes, Ella discovers that Maggie has come to do nothing but sunbathe and take money from her. Maggie asks Ella to finance an acting career for her; Ella agrees to match her salary dollar for dollar if she accepts a job with the assisted living section of her grandmother's retirement community. Meanwhile, Rose has decided to quit her job, become a dog-walker, and date Simon Stein (Mark Feuerstein) whom she had previously ignored. They become engaged.
Maggie is befriended by one of her patients, a blind retired professor of English literature (Norman Lloyd), who has asked Maggie to read works of poetry to him. She does so, but with great difficulty. After asking if she is dyslexic, the professor encourages Maggie to continue reading to him while offering emotional support to her. Maggie finds a friend in the professor, the first person in her life who does not ridicule her difficulties with reading (and actually helps her to improve in this area). As time passes with the professor, Maggie's confidence grows not only with reading but with her general image of herself. In addition, she also becomes friendly with the residents of the retirement community. In doing so, Maggie discovers a livelihood that is greatly needed among the elderly women: a personal clothing shopper, an activity for which Maggie shows enormous talent. Ella (who also does not ridicule her difficulties with math) offers to run the financial aspects of the business. In the process, they become close and resolve their history.
Meanwhile, Rose's reluctance to talk about Maggie is straining her relationships with those around her, such as Simon, her father, and stepmother. While Michael remains oblivious to his daughters' falling out and the stepmother does not care much of the sisters, Simon tries to get Rose to talk about Maggie. When he sees Rose and former boyfriend Jim converse about how Rose cannot talk about Maggie to anyone, Simon's patience has grown thin and effectively dumps Rose after she keeps protecting Maggie by staying silent.
Ella has also secretly contacted Rose and sends a plane ticket asking her to come for a visit. Rose is excited to hear from her long-lost grandmother, but her pleasure quickly sours when she arrives and discovers that her sister already lives there. After a long conversation with Ella, Rose reveals that after Caroline took Rose and Maggie on a spontaneous trip to New York (without Michael's knowledge), Michael and Caroline got into a huge argument, with Michael threatening to put her in a mental institution. Caroline killed herself 2 days later and sent a note to Ella, pleading with her to take care of her daughters. Maggie does not remember this as Rose shielded her from the events to protect her.
Ella never recovered from Caroline's death and never resolved her feelings towards Michael; for she felt he ignored the signs that his wife had problems. The three women bond and learn to resolve their complicated past. Meanwhile, Maggie has contacted Simon telling that Rose is in Florida and "in trouble" and arranges him to meet Rose at the elderly residents' party. The two rekindle their engagement after Rose finally opens up about Maggie's personality and Rose's desire to protect her fearing that Simon will come to hate Maggie.
Before Rose and Simon return to Philadelphia Maggie offers to pick out and buy Rose's wedding dress, as a now seasoned personal shopper she is confident that she can please Rose saying simply "trust me". At Rose's wedding which takes place at the Jamaican Jerk Hut where their first date was. Ella and Michael reconcile and Maggie reads a poem to Rose as a wedding gift which moves Rose to tears.Cameron Diaz as Maggie Feller, a party girl, immature and often petty. She was six years old at the time of her mother's death and had been told by Rose that it was a car accident. She is incapable of reading but later learns how through the help of an elderly man who was once a professor.
Toni Collette as Rose Feller, a plainly-presented workaholic, and very protective of Maggie. She was a bit older than Maggie at the time of their mother's death and knew of her bipolar disorder and knew that she committed suicide.
Shirley MacLaine as Ella Hirsch, Rose and Maggie's grandmother. Carries a lot of guilt for pushing her daughter to always be on her medication and never being there for Rose and Maggie.
Ken Howard as Michael Feller, Rose and Maggie's father. He also carries a lot of guilt for the fight that occurred just days before his wife killed herself, believing that he also "pushed" Ella away after Caroline died.
Brooke Smith as Amy
Candice Azzara as Sydelle Feller, stepmother. Constantly berates Rose and Maggie while bragging about her off-screen daughter, Marcia.
Richard Burgi as Jim Danvers, Rose's office fling. Ended when Maggie slept with him.
Anson Mount as Todd
Mark Feuerstein as Simon Stein, Rose's love interest
Eric Balfour as Grant
Francine Beers as Mrs. Lefkowitz, Ella's best friend
Alan Blumenfeld as Mr. Stein
Andy Powers as Tim
Ivana Miličević as Caroline, Maggie and Rose's mother (in photos). Suffered from Bipolar disorder and subsequently killed herself.
Norman Lloyd as The Professor
Benton Jennings as Shoe Salesman John Johnson
Jennifer Weiner as Smiling woman in Italian market
In Her Shoes has received generally positive reviews from critics. Rotten Tomatoes reported that 75% of the critics gave the film a positive reviews, based on 162 reviews. Metacritic reports an average review score of 60%, based on 36 reviews. Rex Reed in The New York Observer calls In Her Shoes "pure joy" and "a movie to cherish", arguing that Shirley MacLaine has "found her finest role since the Oscar-winning Terms of Endearment [...] funny and poignant, she uses abundant humanity and smart psychology to great advantage, lending her knowledge to the other actors generously." Roger Ebert of the Chicago Sun-Times states that the film "starts out with the materials of an ordinary movie and becomes a rather special one. The emotional payoff at the end is earned, not because we see it coming as the inevitable outcome of the plot, but because it arrives out of the blue and yet, once we think about it, makes perfect sense. It tells us something fundamental and important about a character, it allows her to share that something with those she loves, and it does it in a way we could not possibly anticipate. Like a good poem, it blindsides us with the turn it takes right at the end."
Mick LaSalle of the San Francisco Chronicle argues, on the other hand, that the film "is almost a true statement, almost an honest rendering of a sibling relationship and almost not a sentimental Hallmark card of a movie. But it compromises with itself and ends up in a limbo of meaninglessness, with writer Susannah Grant and director Curtis Hanson strenuously pretending to have told one kind of story, when actually they've told quite another." Carino Chocano of the Los Angeles Times concurs, calling the film "a curious movie, hovering for upward of two hours between light and dark, truth and fake uplift, menace and mollycoddling."
The film opened at #3 at the U.S. Box office raking in $10,017,575 USD in its first opening weekend.
Shirley MacLaineGolden Globe Award for Best Supporting Actress - Motion Picture
Satellite Award for Best Supporting Actress - Motion Picture
Toni ColletteSatellite Award for Best Actress - Motion Picture Drama
Australian Film Institute Award for Best Actress
Cameron DiazImagen Foundation Award for Best Actress