In Her Shoes is a dramatic comedy that focuses on the relationship between two very different sisters. Rose Feller (Toni Collette) is a responsible, hard-working attorney at a prestigious law firm in Philadelphia. Just as she begins a new relationship with her co-worker Jim (Richard Burgi), her sister Maggie (Cameron Diaz) comes to live with her. Maggie is beautiful, reckless, and has no desire to hold down a job or take any of her relationships seriously. She was forced to leave their parents' home after making a series of bad decisions. After discovering Maggie in a compromising position with Jim, Rose decides to end their relationship and throws Maggie out of her apartment. As Rose struggles to come to terms with the deception, Maggie goes to Florida to find Ella (Shirley MacLaine), the grandmother she never knew existed. Maggie's new life and relationships wind up having a dramatic and unexpected impact on both sisters' lives.