The stories behind 12 showstopping rom-com dresses

Gowns to fall in love with

What's a romantic comedy without a breathtaking fashion moment? Here are the untold stories behind a dozen of the most fabulous looks in rom-com history.

Every day until Valentine’s Day, Entertainment Weekly is celebrating our special romantic-comedy-themed Untold Stories issue. Check out all our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram.

Andie (Kate Hudson) in How to Lose a Guy in 10 Days (2003)

The dress that launched a thousand slips at proms across the country was instantly iconic — much to the surprise of designer Karen Patch. “I think Kate said to me once, she never had worn anything that got that much attention,” Patch says. “I mean, it was lovely, and it was perfect, but you know, it’s a simple dress!” And intentionally so: The cool, understated Andie “would have access to samples,” as a writer at a fashion magazine, but “it would have been out of her character to do anything too fussy,” the designer says. “I wanted it to look like it all came together easily.”

Patch cut the neckline of the gown to set off the 51.94-carat yellow sapphire necklace that Andie tries on (Patch chose Harry Winston's “Isadora” necklace, and had a copy made) and designed the open back to suit Hudson’s body, but the trendsetting color wasn’t a lock. “I thought I would probably do contrast,” says Patch. She tested navy and moss green in addition to this matching shade, all in silk charmeuse. “It was kind of unusual at that time for blondes to wear yellow,” Patch says. “And I thought, well, this completely breaks that rule, but who cares?”

Eva (Gabrielle Union) in Deliver Us from Eva (2003)

The classic Shakespearean feel of Eva’s evening look “is a little bit of what I intended,” says costume designer Debraé Little, who put Union in a two-piece outfit by Elie Tahari for the party scene in this Taming of the Shrew update. As this marks the first time the audience sees the high-strung Eva out of her stiff wardrobe, “I wanted it to be eye-catching, but I still wanted it to be somewhat reserved,” Little says, especially in contrast to flashy social climber Renee (Kenya Moore, pre-RHOA). “[She’s] the classic beauty as opposed to the sexy beauty.”

The outfit still signifies that Eva is “slowly becoming this butterfly and opening herself up and being more trusting and open and less controlled,” though, with the bustier’s vivid ruby red. “I think [Union] was a little hesitant about the color,” Little recalls, but the actress got on board after discussions about it. “I told her, ‘This is your moment, you’re making a stance. You’re coming out, so to speak, but you’re showing that you’re strong and you’re powerful,’” Little says. “I felt that red was the color that represented that best.”

Julianne (Julia Roberts) in My Best Friend's Wedding (1997)

Costume designer Jeffrey Kurland’s inspiration for Julianne’s personal style was Katharine Hepburn. But when he was designing a maid of honor dress for her to wear to Kimmy (Cameron Diaz) and Michael’s (Dermot Mulroney) wedding, “I knew, character-wise, that Julianne’s dress had to be something that Julianne would never pick, that it would only be picked by [Kimmy],” says Kurland.

So the idea of this lavender dress — which Kurland modeled after ’50s and ’60s eveningwear, constructed from a vintage piece of silk duchess satin, and beaded at the fitted bodice — “was truly, in a way, horrifying to Julianne,” the designer says. “But at the same time, she looks great in it. In the end, she owned it. Which kind of goes with the whole theory of the movie.”

Georgia (Queen Latifah) in Last Holiday (2006)

“I looked at a lot of Old Hollywood movies,” costume designer Daniel Orlandi says of the inspiration for this dramatic look, which Georgia wears to what she (incorrectly) believes will be one of her last dinners. “We wanted that sweep of chiffon when she walked in and there was a little bit of a breeze.”

The producers wanted red from the beginning, and Orlandi layered hot pink and red chiffon over silk crepe to give the color dimension, “so it sort of shimmers, then when you move it sort of gets that iridescent quality.” It’s a huge change for the heretofore frumpy Georgia, but a welcome one for the designer. “It was harder to make her look kind of plain,” Orlandi admits, “because her personality’s so strong and beautiful.”

Carrie (Sarah Jessica Parker) in Sex and the City (2008)

This voluminous wedding gown by Vivienne Westwood was The One (at first, anyway) for Carrie just as much as Mr. Big (Chris Noth) was — and became as synonymous with the character as her opening-credits tutu. “You know, if something is correct, it takes root,” observes costume designer Patricia Field, who dressed Parker and company throughout the series’ run. “If something is not important, it flies away. It goes with the wind.”

After (spoiler alert?) Carrie is jilted, she complains to her friends about having "put a bird on my head" for their doomed ceremony in “one of those perfect coming-togethers of the costume and the script,” says Field. “That was really cool about the writers; they paid attention to the fashion side of it.” When she finally does make it to the altar (quietly, at City Hall), Carrie wears a “sweet little suit." Field likens the wedding wardrobe disparity to the 1973 fashion battle of Versailles, in which five revered French designers showed opposite five upstart Americans. “That [suit] really contrasted with the dream dress. It helped to describe the entire scene, you know?” she says. “The Versailles wars, visuals that I have seen of it, it was so well-defined, the difference between Paris and U.S. And U.S. won — and deserved it!”

Cher (Alicia Silverstone) in Clueless (1995)

“You don’t understand! This is an Alaïa!” Cher memorably cries when being mugged. Her attacker really didn’t understand — that dress was not easy to get. “This movie was made in the ’90s. There was not so much promo at the time. People [were] not sending [costume] designers dresses like they do now. We also had unknown actors. We had to go to certain designers and make some calls and see who would work with us,” recalls costume designer Mona May. “Alaïa was very helpful. He was one of the designers that really wanted to work with us.”

May opted for the color to keep it Christmassy, and the simple, sophisticated silhouette because “we never wanted to be too frou-frou or too over-designed in a way. I think simplicity was really what kind of Cher looks were. It was always clean.” The dress especially pops when juxtaposed with the juvenile party, where “they're throwing up into the pool and there she is in her beautiful dress with the hair up,” May says. “It was a very grown-up look for her.” It is, after all, like a totally important designer.

Andie (Molly Ringwald) in Pretty in Pink (1986)

“Pretty in Pink was so organized,” says costume deisgner Marilyn Vance. “There were the richies that all wore light blue, beige, whites, light gray. The [zoids] were the guys who wore tough leather, black, chains, or thrift store clothes. And she was one of them.” Even before she makes her pink Franken-dress for the prom, Andie “started to do her own thing. She would sew little charms onto her sweater,” Vance says. “Just all these different concoctions that she [put] together because she couldn't compete with the richies. She didn't even attempt to compete.”

“Unfortunately, in the real world, [Ringwald] loathed that dress,” admits Vance of the DIY prom look, sewn together from two others in a deliberately simple design that incorporated elements from Andie’s existing wardrobe (like the neckline of the top she’s wearing when she’s sketching it). “She wanted to be the Madonna — the strapless with the full skirt. [But] everybody else was doing that. She’s unique. She is not one of those girls.”

Rachel (Constance Wu) in Crazy Rich Asians (2018)

Rachel spends her time in Singapore feeling like a fish out of water, but by the end of Crazy Rich Asians, she’s making a splash. When she arrives at the opulent wedding of her boyfriend’s best friend wearing this ethereal pale blue gown by Marchesa, without the billowy sleeves that appeared on the runway version, Rachel proves she can dress with the crazy-richest of them. It’s a battle of “blue v. blue,” according to costume designer Mary E. Vogt, between Rachel and her boyfriend’s mother (Michelle Yeoh), whose more structured blue Elie Saab outfit contrasts with the heroine’s softer look.

Vivian (Julia Roberts) in Pretty Woman (1990)

Vivian’s fashion evolution “showed how smart she was by knowing that she had to be simpler,” explains costume designer Marilyn Vance, who created Roberts’ custom wardrobe to demonstrate her gradually increasing sophistication. “I pared everything down,” Vance says. “She sees how the other half lives, and she gets it. And she pares herself down to try to fit in.”

For this final proof of Vivian’s mastery of Edward’s (Richard Gere) lifestyle, the studio wanted Roberts in black, but “nothing but red was right,” Vance insists. Finding the right shade required a laborious color-testing process for both designer and actress. “I don’t know if she’d do it today, because it was a lot of work on her part,” Vance says of Roberts. “She worked really, really hard. She was such a sport.” In the end, of course, it was all worth it. Black would have been a big mistake. Big. Huge.

Marisa (Jennifer Lopez) in Maid in Manhattan (2002)

For the museum gala, costume designer Albert Wolsky needed “what would be, without going to a fairy-princess land, a kind of enchanting moment,” he recalls. One evening after shooting, the star and the crew stuck around so she could test 10 different dresses for the camera, narrowing it down to two or three. “Then, as it always happens — I guess it happens at the Oscars — nobody knows what they’re going to wear until the last five minutes,” Wolsky recalls. When the time came, J. Lo herself chose this archival Bob Mackie gown. “It has to be [her decision],” Wolsky says. “She has to feel wonderful in it also, as an actor.”

Giselle (Amy Adams) in Enchanted (2007)

After having spent her time in New York wearing actual princess dresses, Giselle, ironically, has her true Cinderella moment when she shows up to the King’s and Queen’s ball looking sleek and contemporary. “That dress was really inspired by her journey. We did the big sleeves, then we did the empire dress, then we did off the shoulders. What would be next?” says costume designer Mona May. “She was the fairy-tale princess. She's now a modern girl.”

May also had to consider that Giselle would be dancing and “looked at old Fred Astaire movies, how they layered the chiffon dresses” so they would move beautifully; she chose purple because it’s a royal, “magical” color. Ultimately, “it is a Disney character,” she says. “You want to have a follow-through [with] the Disney Princess look, but then make it fresh, make it modern.”

Juliet (Keira Knightley) in Love Actually (2003)

Fashion, actually, is all around at Juliet and Peter’s (Chiwetel Ejiofor) wedding. The bride wore a funky ensemble for her winter ceremony, covering a crop top and long skirt with a sheer, feathery overlay. According to costume designer Joanna Johnston, this was a compromise; director Richard Curtis had envisioned a sexier, barer outfit. The unconventional nuptial look isn’t for everyone, but at least to Mark (Andrew Lincoln), it is perfect.