Love ‘em or hate ‘em, rom-coms have a way of stitching their fashions into pop culture’s collective memory, specifically when it comes to the leading lady’s closet of showstopping gowns. Before these dresses became annual Halloween looks and Pinterest board inspo, they were just fabric and vision — conjured by costume designers who have a keen eye for storytelling.
From the impromptu decision to put Jenna (Jennifer Garner) in her now-iconic Versace mini dress in 13 Going on 30 to the meticulous color testing behind Vivian’s (Julia Roberts) unforgettable red gown in Pretty Woman, these canonical looks all have histories worth remembering. Here’s how they all came to be.
Andie Anderson’s (Kate Hudson) yellow silk slip in How to Lose a Guy in 10 Days (2003)
Everett Collection
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 [Hudson] 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?” —Mary Sollosi
Eva Dandrige’s (Gabrielle Union) two-piece party dress in Deliver Us from Eva (2003)
Everett Collection
The classic Shakespearean feel of Eva’s evening look “is a little bit of what I intended,” says costume designer Debraé Little, who put Gabrielle 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-Real Housewives of Atlanta). “[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.” —M.S.
Jenna Rink’s (Jennifer Garner) Versace mini dress in 13 Going on 30
Everett Collection
The multi-colored striped Versace mini dress Jenna Rink (Jennifer Garner) wears while zombie-walking at her first grown-up party — as a 13-year-old trapped in a 30-year-old’s body — instantly became a piece of pop culture iconography. Yet shockingly enough, none of it was planned.
According to costume designer Susie DeSanto, “The dress really wasn’t premeditated” — as she and her team chose it at the last minute, believing it struck the right balance between girlishness and maturity. “Culture took the dress and went with it,” DeSanto told PEOPLE in April 2024. “The reason I think people fall in love with it is because of Jen. I think anybody else in that role, it would’ve just been a cute movie, but I think right then she was the exact right person with [the] right energy and ability to tap into her youthfulness.” —James Mercadante
Julianne Potter’s (Julia Roberts) lavender maid of honor dress in My Best Friend’s Wedding (1997)
TriStar/Everett Collection
Costume designer Jeffrey Kurland’s inspiration for Julianne’s (Julia Roberts) 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 evening wear, 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.” —M.S.
Georgia Byrd’s (Queen Latifah) red evening gown in Last Holiday (2006)
Stephen Vaughan/Paramount
“I looked at a lot of Old Hollywood movies,” costume designer Daniel Orlandi says of the inspiration for this dramatic look, which Georgia (Queen Latifah) wears to what she 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.” —M.S.
Carrie Bradshaw’s (Sarah Jessica Parker) designer wedding dress and “label-less” wedding suit in Sex and the City (2008)
Everett Collection; New Line Cinema
This voluminous wedding gown by Vivienne Westwood was “the One” — at first, anyway — for Carrie (Sarah Jessica Parker) 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!” —M.S.
Cher Horowitz’s (Alicia Silverstone) red Alaïa minidress in Clueless (1995)
Paramount Pictures
“You don’t understand! This is an Alaïa!” Cher (Alicia Silverstone) memorably cries after being told to lie on the ground when being mugged. Her attacker (Jace Alexander) 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] designer 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. —M.S.
Andie Walsh’s (Molly Ringwald) pink prom dress in Pretty in Pink (1986)
Paramount Pictures
“Pretty in Pink was so organized,” says costume designer 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, [Molly 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.” —M.S.
Rachel Chu’s (Constance Wu) blue Marchesa gown in Crazy Rich Asians (2018)
Sanja Bucko/Warner Bros.
Rachel (Constance Wu) 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 (Henry Golding) best friend (Chris Pang) 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. —M.S.
Vivian Ward’s (Julia Roberts) red evening gown in Pretty Woman (1990)
Snap/REX/Shutterstock
Vivian’s fashion evolution “showed how smart she was by knowing that she had to be simpler,” explains costume designer Marilyn Vance, who created Julia 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 the designer and the 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.” —M.S.
Marisa Ventura’s (Jennifer Lopez) pale pink Bob Mackie dress in Maid in Manhattan (2002)
Columbia/Kobal/REX/Shutterstock
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, Jennifer Lopez 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.” —M.S.
Giselle’s (Amy Adams) purple floor-length gown in Enchanted (2007)
Everett Collection
After having spent her time in New York wearing actual princess dresses, Giselle (Amy Adams), 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.” —M.S.
Samantha “Sam” Montgomery’s (Hilary Duff) white gown in A Cinderella Story (2004)
Warner Brothers/courtesy Everett Collection
Sam Montgomery (Hilary Duff) didn’t need a fairy godmother to prove she was very pretty and very bright — just the right dress for her school’s Halloween dance. However, according to costume designer Denise Wingate, the gown was originally intended to emulate the Disney animated style before ultimately switching gears to a more timeless look.
“When we were first trying to figure out Sam’s dress for the ball, I was harkening back to the original Cinderella, using all of those colored layers with [these] iridescent blue fabrics like you’ve probably seen in the Disney cartoon, and it just didn’t work out. I wanted it to be this colorful thing but after we camera tested it, it ended up looking like a mish-mash,” Wingate told Interview Magazine in 2018. “So we went for something more classic, almost like a wedding dress, and just this beautiful vision of white. It was a Monique Lhuillier dress and it ended up being perfect. And for the mask…we made 12 different masks — there’s a lot of trial and error to get it right when you’re dealing with a statement outfit.” —J.M.
Juliet’s (Keira Knightley) sheer wedding look in Love Actually (2003)
Everett Collection
Fashion, actually, is all around at Juliet’s (Keira Knightley) 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. —M.S.
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