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The Most Stylish Rom-Coms of All Time

Even the ones you might not expect

The Most Stylish Rom-Coms of All Time Even the ones you might not expect

It's still unclear what makes a romantic comedy good or bad. But when it comes to its fashion, it's a different story. While many people watch romantic comedies for humor, love, and fondness, fashionistas all over the world turn on their televisions and put on one of these movies to analyze the incredible closet of rom-coms. A stress-free genre, romantic comedies are labeled as a comfort zone of cinema, one that besides evoking a sense of nostalgia and featuring authentic fashion from specific eras in the story.  

Sabrina (1954) 

Directed by Billy Wilder, Sabrina follows the introspective young daughter of a wealthy Long Island family's driver, Sabrina Fairchild, played by Audrey Hepburn. All her life she has been in love with one of the household's sons, the playboy David Larrabee, who hardly notices her presence. That is until she goes to Paris for two years and returns as an elegant and refined lady. Then, not only does David exhibit interest, but so does his serious and hard-working brother, Linus. Matters become complicated as Sabrina finds herself in love with both of them. 

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While the movie is famous for its drama and the characters' transformation, it has also become known for having created fashion's most iconic designer-muse relationship: Hubert Givenchy and Audrey Hepburn. From the black cocktail dress with bows on the shoulders to the iconic Sabrina organza dress with its embroidered and beaded bodice, Givenchy and Hepburn teamed up to prove that the actress once again triumphs as the protagonist in the romantic comedy fashion discourse. 

Pretty in Pink (1986) 

A nostalgic glimpse into the world of 1980s teen romance, Howard Deutch's Pretty in Pink centers on Andie Walsh, played by Molly Ringwald, an unpopular and poor teenager who has to decide between the feelings of her childhood friend, Duckie, or a wealthy boy, Blaine. Whether through retro glasses, a "volcano ensemble," a mash-up of two pink dresses for prom, or sleek beige suits, Pretty in Pink offers not just love fever but raw 1980s style too. 

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My Best Friend's Wedding (1997)

My Best Friend's Wedding is defined by some as a romantic comedy about finding your heart and losing your head. The movie follows best friends Julianne, played by Julia Roberts, and Michael, starring Dermot Mulroney, who years ago made a pact that if they weren't married by 28, they would get together and tie the knot. Then, near Julianne's 28th birthday, he calls her and finally pops the question – to someone else. With a few days before the marriage, she realizes she loves him herself and tries to break off the wedding. From Cameron Diaz's character Kimberley in a vivid yellow dress to Julianne's lavender maid of honor gown, the fashion is as interesting as the plot. 

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 How Stella Got Her Groove Back (1998) 

How Stella Got Her Groove Back stars Angela Bassett. Stella, a successful forty-something San Francisco stockbroker, is convinced by her New Yorker friend to take a vacation to Jamaica. Against all odds, she falls in love with a man half her age, Winston Shakespeare, played by Taye Diggs

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The production, which explores themes of companionship, maturity, responsibility, and love, is famous for Bassett's acclaimed performance, beautiful scenery, and fashion-forward wardrobe. The film's looks are a product of Academy Award-winning costume designer Ruth E. Carter. As a golden ticket to '90s classics, it includes classic Princess Diana athleisure, Susan Lazar's sultry silhouettes, crochet dresses, corporate wear, and the decade's minimalism with a touch of early 2000s maximalism.

10 Things I Hate About You (1999)

The 2007 adaptation of William Shakespeare's The Taming of the Shrew, 10 Things I Hate About You, directed by Gil Junger and starring Heath Ledger, Julia Stiles, and Joseph Gordon-Levitt, has maintained its iconic status to this day. The narrative follows a high school student, Cameron, who can't date the popular girl, Bianca, until her nonconformist older sister, Kat, has a boyfriend. Therefore, his friend, Michael, assists him in persuading the wealthy and somewhat unpleasant Joey that he will get to take Bianca out if he pays someone to take out Kat. His choice is Patrick Verona, a young man with a mysterious reputation.

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Despite all the obstacles and dramas, one thing is for sure: the movie screams early 2000s fashion. From Kat's casual, cool-girl wardrobe to Bianca's iconic line, "I like my Sketchers, but I love my Prada backpack," while wearing a girly strap white minidress with floral print, the film is a fashion masterpiece that still has us falling in love.

Never Been Kissed (1999)

Starring Drew Barrymore as a newspaper reporter who enrolls in high school as part of research for a story, Never Been Kissed by Raja Gosnell explores themes of regret, the uncomfortable nature of adolescence, and the rediscovery of love. Once in school, the protagonist returns to her old student life - then known as Josie Grossie, with no friends and often bullied by her schoolmates. Seeing her job as an opportunity to correct past mistakes, she gets a makeover with the assistance of her brother and becomes friends with the popular group. While pretending to be a teenager, the problems of adulthood don't disappear. And when Josie falls in love with an English teacher she must write about in her article, she faces a challenging conflict – choosing her career or her heart? Plot aside, fashion-wise, moments like Josie's shiny pink prom dress, her flashy white feather-boa look, and the trio of mean girls' daring printed and vivid colored outfits balance out all the drama in the movie. 

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She’s All That (1999)

Robert Iscove's She's All That follows Zack Siler, a high school athlete portrayed by Freddie Prinze Jr, after being rejected by his super popular girlfriend, betting with his mates that he can turn a nerdy girl into the school's prom queen. The girl in question is Laney Boggs, played by actress Rachael Leigh Cook, and as time goes by, Zack starts falling for her. From Laney's red party dress to the sparkly prom gowns, the film continues to entertain to this day, and even had a remake in 2021 called He's All That, where the roles were reversed. 

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Sweet Home Alabama (2002)

Sometimes what we are looking for is right where we left it. At least that is the lesson of Sweet Home Alabama, directed by Andy Tennant. Starring Reese Witherspoon as Melanie Smooter, a young designer who has reinvented herself in New York, the film tells the story of how, after being proposed to by her dream boyfriend, she must return to her home in the South, Alabama, and obtain a divorce from her husband after seven years of separation. With a crucial part in portraying Melanie's transformation from New York socialite to country girl, the movie's fashion moves between elegant all black city style and country-casual one. 

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How to Lose a Guy in 10 days (2003) 

Starring Kate Hudson and Matthew McConaughey, How to Lose a Guy in 10 Days could not be left off this list. Donald Petrie's production revolves around how the paths of journalist Andie Anderson and Benjamin Barr, an advertising executive, meet with a simultaneous dating bet – and make one fall in love. From Andie's iconic yellow silk slip dress to the working-girl looks of pencil skirts, blazers, and typical office wear, the film combines all the best elements of rom-coms: bets on love, a woman who works at a New York magazine, and a style to die for.

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Enchanted (2007)

With the real and the animated worlds colliding, Enchanted, directed by Kevin Lima, is sure to enchant its audience. The film centers around Princess Giselle, played by Amy Adams, who is exiled from the magical, musical, animated kingdom of Andalasia by the malevolent queen and subsequently transported to modern New York City. In an unknown land, she befriends a divorce lawyer, Robert Philip, played by Patrick Dempsey, while hoping to be rescued by Edward, the prince she is promised, performed by James Marsden. But as time goes by she seems to be more and more at home in the real world and has fallen in love with Robert. Its fashion features a bit of everything. From evil Queen Narissa in Thierry Mugler's 1980s designs and John Galliano's looks to Giselle's princess-like dresses, the movie combines the best of both worlds – modernity and imagination. 

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27 dresses (2008) 

Always the bridesmaid, never the bride. That's pretty much what defines Anne Fletcher's 27 Dresses. Starring Katherine Heigl as Jane, a young woman with an entire closet of bridesmaid dresses ranging from inoffensive-bland to ultra-bizarre pieces, who is in love with her boss, George. However, her younger sister, Tess, arrives in town and slowly catches his heart.

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With 27 dresses dedicated to just marriages, it's clear that the movie would have an endless supply of fashion – be it a perfect fit or not. The less favorable looks, such as the full SCUBA outfit for an underwater ceremony and the Gone With the Wind look, are compensated by the more flattering ones – including the gold and pink saree, the pink chiffon dress, the light blue with bolero jacket, and finally Jane's sleek wedding gown.  

Wild Child (2008)

In Nick Moore's Wild Child, Emma Roberts plays Poppy Moore, a rebellious Los Angeles teen socialite who's sent to Abbey Mount, a strict English boarding school by her father. In a new country with new rules, and far from going home, she realizes that the only way to return to her old Malibu life is to be expelled. Over time, though, she gets close to a group of girls, and the school principal's son, Freddie. As a result, she's divided between her old life and her new one. In terms of the film's fashion, one can argue that it's pretty much divided too. As Poppy transitions from her iconic L.A. socialite style—which includes carrying Louis Vuitton monogram bags, wearing giant sunglasses, and wearing loud clothes—to the preppy uniforms of her new school and casual 16-year-old looks, she undergoes a stylistic metamorphosis that reflects her journey of self-discovery.

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Monte Carlo (2011) 

The film Monte Carlo, directed by Thomas Bezucha, features Selena Gomez as Grace, a teenage Texan girl. Leighton Meester plays Meg, Grace's responsible step-sister and Katie Cassidy portrays Emma, Grace's lighthearted best friend. The plot revolves around Grace being mistaken for a British heiress, Cornelia Winthrop Scott, thereby having the group embark on an adventure to Monte Carlo, where she will be impersonating the heiress in an event. The trio lives the dream with a lavish wardrobe that varies from ball gowns from Dior, Oscar de la Renta, and J. Mendel to shoes and clothes galore filled with designer clothing and accessories. But under Cordelia's identity, Grace develops a closer bond with Theo, the son of the event organizer. 

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Crazy Rich Asians (2018)

Adapted from Kevin Kwan’s 2013 best seller, Crazy Rich Asians follows Constance Wu as Rachel Chu, an American-born Chinese NYU professor who travels with her boyfriend, Henry Golding as Nick Young, to his hometown in Singapore for his friend's marriage. There, she'll meet his friends and also his ultra-wealthy family. Since Nick is considered the most eligible bachelor in Asia, every woman in the region is envious of Rachel and attempts to sabotage her relationship, including his disapproving family. 

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The characters wear couture at parties to make a grand entrance and be noticed. For instance, Nick’s glamorous cousin Astrid, played by Gemma Hard, has a wardrobe that varies from a hot-pink, jewel-collared Alexander McQueen gown to a pale-pink drop-waist dress with a high shawl collar by Dior. But among the international brands featured in the film, there are local luxury labels such as Michael Cinco and LORD's Tailor. From Araminta Lee's glamorous liquid gold jumpsuit to Rachel's blue ruffled ball gown, every look conveys a message without saying a word. The louder look in the movie is Lee's multilayered wedding dress, with incredible attention to detail, decorated with thousands of Swarovski crystals, and even waterproof.

Emma (2020) 

When one is in a love obsession or Regency-era style mania, watch Emma to relieve the urge. The period romantic comedy directed by Autumn de Wilde and based on Jane Austen's classic, stars Anya Taylor-Joy as Emma, a clever and rich lady in 1800s England who interferes in the love lives of her neighbors and friends. 

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As for its fashion, Academy Award-winning costume designer Alexandra Byrne told Entertainment Weekly back in 2021 that Emma has the right clothes for the right occasion, the right season, and the right time of day. The variable, almost seasonal color palette, used as a visual representation of Emma's evolving character, was combined with definitive, period-accurate fabrics, silhouettes, and details such as empire waists, capes, bows, ruffled collars, feathers, and bonnets