10 Movies Like Confessions of a Shopaholic

I have often imagined draping the exquisite emerald-colored scarf around my neck ever since I watched the movie Confessions of a Shopaholic (2009) as a teen. The film is directed by P.J. Hogan and based on the first two novels of bestselling writer Sophie Kinsella’s Shopaholic series, the film is like an ice cream sundae to a kid. It consists of all the right elements that make an American rom-com great – high-end drama, a compelling protagonist, a blooming romance that flowers only toward the end of the film, and some self-realization. It plays at the backdrop of the glittery material world of fashion and creative journalism.

Rebecca Bloomwood, played by Isla Fisher, is (simply put) addicted to shopping. A journalist by profession, she dreams of joining a fashion magazine, yet when the right opportunity knocks at her door, she looks past it for a particular green scarf that spots in a shop window. Soon, she climbs the heights of success as a writer, writing as the Girl in the Green Scarf, but realizes quickly that she has amassed a debt of over 16,000 dollars because of her shopping exploits. The film follows her as she redeems herself from her curious obsession. Sweet? It makes you crave rom-coms that nestle themselves in this universe of luxury and silliness.

While most of the rom-coms in the last 90s and the early 20s played around similar characters and settings (who hasn’t fangirled over Carrie Bradshaw from Sex and the City?), we have specially curated a list of 10 movies like Confessions of a Shopaholic that you’ll particularly enjoy if you wish to explore the color-popping world of fashion and creative journalism in films across the genres of drama and rom-com. Happy Reading!

1. Beauty and the Briefcase (2010)

Based on the Diary of a Working Girl by Daniella Brodsky and directed by Gil Junger, this is a lesser talked about American rom-com starring Hilary Duff as the protagonist, Lane, an aspiring writer. She takes on a special assignment that requires her to go undercover, so she sabotages into the role of an Administrative Assistant under the Managing Director, Tom Rinehart, played by Michael McMillian, of a major strategic planning firm. Tom soon realizes that Lane lacks the adequate qualifications and the real reason behind her presence in the firm. Does her unique assignment gets fulfilled? This movie could almost be considered a double bill to Confessions of a Shopaholic.

Rebecca and Lane are aspiring writers who wish to work for fashion magazines. Both of them land themselves a task, alright, and must outdo the challenges that come at them, especially in the form of their boss-turned-lover. Their journeys are as much about self-realization as about breaking the bubble they inhabit – a lazy weekend watch if you have some popcorn and snacks handy!

2. The Devil Wears Prada (2006)

Here’s one of my most favorite film recommendations on this list that I still go back to time and again to cheer myself up on gloomy days. Directed by David Frankel and starring Meryl Streep, Anne Hathaway, and Emily Blunt, this is the story of Andrea, a fresh graduate and aspiring journalist, who lands herself a job as personal assistant to the editor-in-chief of the famous Runway magazine, Miranda Priestley. Poor Andy is initially clueless as she navigates the fashion-conscious world in her tweed skirts, but she soon undergoes a stylish makeover under Nigel’s influence. But the Paris Fashion Week gives her a chance to understand the grim realities of the fashion world, making her take a leap of faith. It is a witty film that seeks to expose the New York fashion scene from the early 2000s but becomes a masterclass in fashion drama because of the performances of Streep and Hathaway.

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Andrea is nothing like Rebecca. Her understanding of fashion and the material culture only develops in the latter half of the film, while Rebecca is teeming with her false notions around it. However, here we have the hate-love relationship between the bosses and these protagonists, the relationship which forms the focal point of both the films. They are saucy fashion dramas with a point to make about the fashion world if you can look past the humor and the sartorial displays.

3. Cruella (2021)

Cruella de Vil is a fictional villain character from the famous novel, The Hundred and One Dalmatians (1956) by Dodie Smith. Emma Stone plays Cruella in this crime-comedy origin story of the character directed by Craig Gillespie. Estella (Cruella’s real identity before she decides to fashion an alter-ego) is born with unusual hair – part white, part black. She is creative and has a penchant for fashion; hitting upon hard luck, she becomes a skilled thief and a janitor at her dream department store but soon lands a job at a fashion house under the haute couture fashion empress, Baroness von Hellman (played by Emma Thompson). She soon realizes the evil truth behind Hellman’s heirloom necklace and is at loggerheads with her in the fashion world. Fashion drama meets a tale of revenge in this making-of-villain story. What a fashionably wild ride! The film also won in the category of Best Costume Design and was nominated for Best Makeup and Hairstyling at the Academy Awards, 2022.

Estella and Rebecca are both shown to grow up with a love for fashion and clothes. Both the narratives inform us that growing up, they were influenced by their mothers. While Rebecca’s story has all the rom-com elements, Cruella’s story is markedly different in its penchant for revenge. However, both the films deal with embracing their identities, albeit with a slight modification to fit their growth as human beings in society. They also showcase the best of retail and high fashion of their times.

4. Funny Face (1957)

One of the most fashionable American musicals directed by Stanley Donen and featuring Audrey Hepburn as the protagonist Jo Stockton, this is a classic Hollywood film for every fashion-drama lover. The editor of Quality Magazine, Maggie (played by Kay Thompson) finds the perfect mix of beauty and intellect in Jo, an assistant in a book store from Greenwich village who wishes to visit Paris to attend the philosophy lectures on empathicalism by Professor Emile Flostre. Jo ends up in Paris but as the new face for Quality Magazine. She is torn between the worlds of fashion and academics until life shows her the way. In this film, Hepburn also romances Dick Avery, the photographer played by Fred Astaire. They go around some of the most beautiful Paris locales, clicking her photos for the magazine in some of the most exquisite clothes.

Jo and Rebecca could not be more dissimilar. Whereas Rebecca is obsessed with clothes and how she styles them, becoming furious when a fellow shopper claims the pair of Gucci boots that she first spotted at the sale, Jo refuses to have her hair chopped and her eyebrows done by a team of makeover artists because she doesn’t care about it enough. Yet, both of them are equally naïve in the decisions they take, being primarily commanded by their extreme interest (not necessarily obsession) in something. The stories head towards a similar epiphany; even the romantic union, in the end, is similar and intricately linked with their first association with their partner, romantic and otherwise.

5. The Intern (2015)

Directed, written, and produced by Nancy Meyers, this is a feel-good American comedy for all ages, whether or not you are interested in fashion. Jules, played by Anne Hathaway, is a founder and CEO of an ecommerce fashion startup. As part of her company’s new outreach program, she employs Ben, played by Robert De Niro, to be a senior intern. Ben and Jules soon become friends, while their personal lives undergo a makeover. It is a heartwarming story of friendship that hits the sweet spot for everyone in our generation trying to find the middle ground between our professional and personal lives.

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Rebecca doesn’t even call to mind when we think of either Jules or Ben. But we must also understand here that the entire setup of the fashion industry has changed with the Internet revolution. Now, we have an ecommerce space, and its work environment is very corporate-like. In that setup, the relationship between Jules and Ben can easily be a modern-day reflection of the relationship that Rebecca shared with her boss, Luke Brandon, sans the romance. It follows the same hate-to-love trajectory that most romcoms are notorious for showing the employer-employee relationship. It is an enjoyable weekend watch, especially with De Niro’s gullible smiling face. Just get yourself some popcorn and tissues!

Stream it on Netflix.

6. Desperately Seeking Susan (1985)

Directed by Susan Seidelman and wildly popular because of Madonna’s maiden appearance in a feature film, Desperately Seeking Susan follows the story of Roberta and Susan. They come together after reading the ‘personals’ in one of the NY city newspaper columns. In one such classified ad, Susan is being desperately sought by her lover, who asks her to come for a rendezvous at Battery Park. Roberta goes to witness this union and follows Susan, only to land up with her thrifted jacket. She re-begins the ‘Desperately Seeking Susan’ column in the newspaper, grabbing some unwarranted attention. What follows is no less than a Shakespearean comedy! It can leave you a little confused in the beginning; hold on till the end. It is a wacky, nostalgic 80s ride for the old-school hearts.

I chose this film because of its curious case of jumbled up and mistaken identities, something that even Rebecca is a part of with her new column. The mistaken identity is very much a driving force of what is to come in the protagonists’ lives in both films. Besides, the toe-to-hat shots in both films constantly draw our attention to the complete outfit of the protagonists. Like Rebecca’s green scarf, a pair of earrings and a jacket – material items – stir the plot into a complication. Anyway, who can miss the sweet ending?

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7. Aisha (2010)

There have been several adaptations of Jane Austen’s Emma. Among them, the film, Clueless, a 1995 coming-of-age comedy directed by Amy Heckerling, certainly defined the style statement of the 90s American High School. However, Aisha, a Hindi-language adaptation of Emma directed by Rajshree Ojha and starring Sonam Kapoor and Abhay Deol as the protagonists, is the most fashionable Hindi-language bourgeois drama of the past decade. Aisha believes that she is the perfect matchmaker and goes around trying to set up her friends with partners she picks for them. But love is more complicated than that, and soon she comes under its radar as well. It is a perfect popcorn-watch with your girlfriends on a sleepover night.

Aisha and Rebecca are alike in their love for fashion and clothes. Both the films put forth an elaborate display of clothes, accessories, and glam-up routines. Aisha, just like Rebecca, is blind to her superficiality. The characters also follow the typical coming-of-age narrative. Most importantly, this is the perfect film to watch if you like slick date-flicks.

8. Mahogany (1975)

Directed by Berry Gordy and starring Diana Ross and Anthony Perkins, this is a camp fashion drama from the 70s that gives you a taste of how the narrative around the female protagonist in dramas like this has changed with time. Tracy, played by Ross, is an aspiring fashion designer ready to work hard to achieve her dreams in the fashion world. To that extent, she takes night classes after working in the store all day. However, it is the presence of men that complicates her life. She gets into a relationship with Brian, goes to Rome as Sean’s muse, and later becomes a demanding and cruel employer. Come for Ross, and stay for the display of the fashion montage of the 70s and the beautiful title track!

The story hasn’t aged well, I agree. The latent misogyny and women-hating make the film a tough watch, so you must keep the period in mind. It is lush soap opera! Tracy shares the same indomitable spirit as Rebecca. They are both pop culture fashion icons in ways, with a deep-seated interest in the contemporary fashion world. Tracy’s journey tells us how difficult it is to climb the ladders of success in this world, especially as a black woman. Both Rebecca and Tracy’s real journey is to self-realization in this film, be it about love or the limitations of the material world.

The last two films are very unconventional but equally interesting recommendations. Hear us out:

9. The September Issue (2009)

This one’s an offbeat recommendation if your only take away from the said fashion comedy is a curiosity about the fashion world, in general. Directed by R.J. Cutler, this fashion documentary takes us through the many processes employed by Ann Wintour, Editor-in-Chief of the Vogue. We are particularly concerned with the production of the September 2007 Issue of the American Vogue in this film.

The plot primarily hinges on the symbiotic relationship between Wintour and her creative director, Grace Coddington, which can be quite uncomfortable to witness because of Wintour’s cold-as-ice attitude against Coddington’s affluent creative ideas. There’s a game of power and words at display between them which can make you want to pick sides. Sadly, Wintour’s moves portray the disturbing truths of how marketing and storyboarding work in the material culture of the current century. But the documentary doesn’t focus on Wintour alone. It is about the team at work which gets the work done. Famous designers and models, such as Jean-Paul Gaultier, Oscar de la Renta, Sienna Miller, etc., make their way into the frame to make you baffle at the scale of work we are looking at here. It is an essential microscopic view of the grander schemes of fashion in the 2000s.

10. Ready to wear (1994)

Prêt-à-Porter, or Ready to Wear, directed, written, and produced by Robert Altman, astonishes me to think that it was shot during the Paris Fashion Week, on location. Unfortunately, Olivier de la Fontaine, the Head of Fashion Council, chokes to death, triggering an investigation, some gossip, and bickering. It is a hilarious satire on the 90s fashion world that reminds you of the children’s story, The Emperor’s New Clothes, involving journalists at tryst, crowd-pleasers, old-school romance, nosy photographers, and other stereotypes. Despite the glorious cast, it can feel a little overwhelming by the end. It can be a 90-minutes-long delicious treat if you love to gossip and fashion dramas, also providing you an entry into the world of Altman’s legendary filmmaking techniques. It again breaks down the truths behind the material culture in the 1990s in a weird mix between a home comedy and a fashion drama, popularly perceived as a hate letter to the fashion industry.