Fashion and cinema are a combination that’s gone together for as long as the art of film has existed. Movies like The Devil Wears Prada is beloved not only for being a fun dramatic comedy, but for having the perfect proportion of excellent costume design to fashion commentary. A great costume department can make what might have been an adequate rom-com into a classic. Though that isn’t to say the film is merely an adequate example; fans of The Devil Wears Prada are just as enamored by the story of an ambitious journalist working her way to success as they are by the fashion.
Titles that combine our love for fashion along with our love of chick flicks feel like they should be easier to find, but getting that great balance is harder than it looks. As a fellow fan of fashionable films, I did my best to come up with a list of 10 movies that fit within the middle of the Venn diagram that is fashion and romantic comedy, and while some of these skew one way or the other, I hope you’ll agree that they’re worth a watch.
Confessions of a Shopaholic (2009)
Much like The Devil Wears Prada, Confessions of a Shopaholic is based off a book. Like Andy, the film’s protagonist is an aspiring journalist, but unlike Andy, she’s violently addicted to shopping, an addiction that she’s racked up thousands in debt to feed. Somehow, Becky (Isla Fisher) is an endearing main character, even as she continues to make some morally questionable decisions, like writing a finance column for a frugal magazine as she struggles to pay off her debt. This film follows a predictable formula but, boy, do I eat it up every time.
Morning Glory (2009)
While there’s not much going for Morning Glory in terms of fashion, don’t write it off yet; in terms of story, there’s a lot of similarities with The Devil Wears Prada. Becky (Rachel McAdams) has been dreaming of being a news producer since she was a young child, and after losing a gig on Good Morning New Jersey, she takes a job with the struggling morning show DayBreak. She finds herself in over her head trying to save the struggling program and frequently fighting with Mike Pomeroy (Harrison Ford), the senior news reporter she ropes into co-hosting the show. As expected, a movie starring McAdams and Ford is a delight to watch.
Fashion (2008)
The 2008 film Fashion has a darker and more serious tones than the movies listed so far. Starring Priyanka Chopra Jonas as an aspiring model named Meghna, it explores the seedier side of the fashion industry, showing abuse, sexual exploitation, and rampant drug use. Throughout the narrative, Meghna and her friends experience the highs and lows of fame as they navigate an industry that can end a star’s career just as quickly as it can make them.
Clueless (1995)
A list about fashionable and girly films without mentioning Clueless? As if! This modern-day retelling of Jane Austen’s novel Emma is set in the fantasy-land of Beverly Hills and follows multiple fashionable teenagers, particularly Cher Horowitz, who is as revered for her bubbly personality as she is her fashion sense. Though she means well, Cher’s attempts at playing matchmaker for her teacher’s and giving advice to her friends don’t always play out as well as she envisioned. Despite this, she’s always serving looks in every scene.
Ready to Wear (Prêt-à-Porter) (1994)
Ready to Wear was filmed on location at Paris Fashion Week during the Spring/Summer 1994 season, and combines fashion with crime and comedy. Early during the event, the head of the Fashion Council dies suddenly and nearly everyone is a suspect. The film has a stacked cast, featuring Julia Roberts, Sophia Loren, Forest Whitaker, and even Cher, and while it’s satirical plot is mostly improvised and haphazard, spotting all the familiar faces can be fun.
13 Going on 30 (2004)
As the title implies, Jenna Rink is a newly 13 year-old girl who desperately wishes to be “30, flirty, and thriving.” The next morning, she wakes up in her 30-year-old body (Jennifer Garner) with no memory of the past 17 years, but with a glamorous adult life and apartment. She finds that her dream of becoming a popular fashion magazine editor has come true, but soon realizes her adult life isn’t as great as it seems.
Cruella (2021)
This live-action film about the infamous villain from One Hundred and One Dalmatians follows some similar beats as The Devil Wears Prada (and even shares a writer in Aline Brosh McKenna). With the punk scene of a 1970s London as the background, young aspiring designer named Estella (Emma Stone) begins working for the very Miranda Priestly-like Baroness von Hellman (Emma Thompson). The two frequently clash as events lead to Estella adopting the alter-ego “Cruella,” and embarking on a life of crime.
Working Girl (1988)
In this film, Melanie Griffith stars as Tess, an intelligent corporate woman who dreams of making it big in business as an executive. Fed up with being looked down upon, she quits her job as a secretary at a stockbroker firm to become an administrative assistant for an associate at Mergers & Acquisitions named Katherine (Sigourney Weaver). When Katherine suffers a bad injury during a ski trip, Tess house-sits for her boss, only to find that Katherine was planning on presenting one of Tess’ ideas as her own. There’s a lot of deception and backstabbing to be found – if that’s your thing – and also a very handsome Harrison Ford.
The Proposal (2009)
If you ever watched The Devil Wears Prada and thought, “what if Andy and Miranda fell in love?,” then you might like The Proposal. Granted, Ryan Reynolds is not Anne Hathaway, but we can’t always get what we want. Margaret Tate (Sandra Bullock) is a Canadian executive for a New York company who learns her visa application has been denied. Desperate to not get deported, she blackmails her assistant Andrew (Ryan Reynolds) into marrying her, which would be pretty messed up in real life, but is a fun set up for a romantic comedy.
The Intern (2015)
The Intern is like The Devil Wears Prada if Hathaway got to play the executive. Unlike Miranda, the actress’ Jules Ostin is a lot nicer to her intern, the 70 year-old Ben Whitaker, who applies for a position as a “senior” intern when he starts to find retired life a little boring. The two prove unlikely friends, helping each other face their own personal problems with a little comedy and a lot of heart. This is a feel-good movie through and through.
