The movie starts off with a flashback of when Rebecca was young, her mom buys her brown shoes that will last forever but aren't very fashionable, while the other little girls in the store are getting cute fashionable shoes. When they look at her mundane shoes, they laugh at her and its at that moment that Rebecca first feels unworthy.
The movie flashes forward to the present, Rebecca Bloomwood , living with her best friend Suze Cleath , has moved to Manhattan to nurture her shopping addiction and to get involved in the New York City magazine world. She's a journalist for a garden magazine but she'd rather work for the fashion magazine "Alette". Unfortunately for Rebecca, when she gets to her interview she's told by the male receptionist that the job has been filled. He helps her out by giving her a tip that she should get her foot in the door with another magazine owned by the corporation and then make her way up to "Alette" since the company, Dantay West that owns all the magazines, likes to promote from within, he tells her there are interviews being held at the magazine "Successful Saving."
Rebecca is off to the interview but on the way there she realizes that there is a sale at Denny & George. Inside she finds a beautiful green scarf. Unfortunately her credit card is declined and the sales girl tells her that they can't hold sale items. Rebecca races to the nearest hot dog stand and offers to buy all the hot dogs if he gives her back change in cash. Rebecca lies and says its for her Aunt Ermintrude who is sick in the hospital and she needs the scarf. Finally a man offers her money so she can buy the scarf. When she interviews with Luke Brandon , the editor of the magazine Successful Saving, she finds that he is the man from whom she had borrowed money. While he's still talking on the phone, she throws off her scarf on one of the cubicles and tries to act like its not hers. The interview doesn't go well for Rebecca, when he asks her what Finnish she speaks and about the current fiscal crisis. She tries to distract him but it all goes badly. Luke's assistant Hayley comes into the room and tells Rebecca that she dropped her scarf. Rebecca knows her game is up and leaves the interview.
Frustrated by her lack of success, she and Suze write drunken letters to Alette magazine and Successful Saving, but she posts each one to the wrong magazine. Nevertheless, Luke Brandon hires her. Then, rather than completing a work assignment, she goes to a clothing sale. When examining an expensive cashmere coat, she realizes that it is 5% cashmere and 95% acrylic. She writes her column, calling herself "the Girl in the Green Scarf". Impressed, her boss, Luke, invites her to a conference in Miami and an important ball. While shopping for the ball, Luke asks what she thinks of him. Rebecca says he is a workaholic and not a good investment as all his hard work goes into the magazine but the earnings to someone else. At a restaurant, another woman, Alicia Billington , asks Luke to the ball. Rebecca learns that Luke is the son of the famous socialite Elinor Sherman and that he knows a lot about clothes. At the ball the two share a romantic moment on the roof.
Rebecca returns home to confrontations with a bill collector and her best friend Suze, who makes her join a Shopaholic-group. Her Shopaholic class leader, Miss Korch , forces her to sell all the clothes she just bought, including her bridesmaid dress. She is later publicly accused of not paying her debts live on a TV show, 'Morning Coffee' and as a consequence loses her job. Though Luke is hurt that Rebecca has lied to him, he still finds her a source of inspiration. Suze finds out that Rebecca sold her maid of honor dress, and forces her to move out.
Rebecca decides to sell all of her clothes in a sale, but hesitates over the green scarf. A blond woman and a woman talking on a telephone begin a bidding war over the scarf. The sale is a success, making it possible for her to repay her debt. Rebecca attends Suze's wedding, and she forgives her, letting her be the maid of honor. Rebecca and Luke come together, with Luke returning her the green scarf;– he was the person behind both bidders. During the credits, Rebecca ends up working for Luke's new magazine, writing articles such as "Confessions of a Shopaholic".
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