9 Iconic Rom-Com Looks (and the Secret Stories Behind Them)

The one thing all romantic comedies have in common? They celebrate the two things everyone wants in life—rom and com, of course. To honor that, we're devoting a whole week to the genre. More on the rom-coms we love, past and present, here.

In a romantic comedy, the fashion helps tell the story just as much as the dialogue—especially if that story involves a transformation. If a character goes from wearing all black to pastels, for example, that might signify a change in mood from dark to light. If she goes from wearing pajamas to power suits (or the other way around), it might suggest an increase in confidence or a decrease in stress levels. Whatever the case, a rom-com character’s choice in clothing is anything but an accident.

Here, we ask costume designers to share their behind-the-scenes stories about nine iconic looks in romantic comedies to prove just that. Find out how Jennifer Garner's 13 Going on 30 "Thriller" dress came to be, surprising details about The Wedding Planner wardrobe, and so much more.

13 Going on 30 (2004)

One of the most memorable scenes from Jennifer Garner’s Ariana Grande–approved romantic comedy—in which Garner plays Jenna, a sweet 13-year-old girl who wakes up as a cutthroat 30-year-old magazine editor—is when she dances to “Thriller” in a showstopping Versace dress. Below, costume designer Susie DeSanto explains the look.

There was so much attention and pressure put on that dress, I couldn’t even begin to tell you. It was like it was the only dress that was ever going to be worn in the history of movies! The director, Gary Winick, was very knowledgeable in fashion. He grew up on the Upper East Side of New York, his mother took him to Bergdorf Goodman every Saturday…but he didn’t want things to be fashion for fashion’s sake. He needed it to tell the story of Jenna finding her way back to her authentic self.

So he wanted [the "Thriller" scene] to feature a dress that, ultimately, Jenna, when she’s further in her journey, would never choose. It’s too loud, it’s too attention getting, it’s just too much of everything. Then, once she rekindles her romance with Matt [her childhood best friend played by Mark Ruffalo], the fashion needed to be more romantic and sweet because that is essentially who this girl was. There was an Alberta Feretti skirt, that sort of lavender one that she wears when they’re walking on the Brooklyn Bridge. And there was a yellow Marc Jacobs skirt that we paired with a Ralph Lauren flowered bustier. Jen really loved that.

There couldn’t have been a better way for her to start her movie-star career than this role. It was in the heyday of Alias, so everybody was so used to seeing her as the spy on TV, doing all those crazy stunts and wearing all those crazy costumes—which was what made Alias so awesome. But then to have this be her movie, I think you really got to see Jen shine for the kinds of qualities that she has, that people to this day still love her for.

The “Thriller” dance is one of the scenes in the movie that you never forget. The dress really needed to allow for that big, attention-getting moment where a whole room of people turn and look at you, like, What? But it was Jen who made that scene work. I was like, “Oh my god, what a tough day this is going to be for her.” But she just went out there and killed it. Her energy never lagged.

How Stella Got Her Groove Back (1998)

Stella (Angela Bassett) is a successful stockbroker whose best friend, played by Whoopi Goldberg, convinces her to cut loose for a change on a trip to Jamaica. While there, Stella meets a 20-year-old man (Taye Diggs) who changes her life for good. Below, costumer designer Ruth E. Carter explains Stella’s vibrant vacation wardrobe, starting with the pink number she’s first seen wearing on the beach.

I remember dyeing her jogging outfit myself in my room in Jamaica, and I made it this pink because of all of the bougainvillea and the beautiful turquoise sea and the sky. The movie was about a girl who meets a guy and falls in love, and I feel like the more color you represent, the better. With bathing suits, you don’t have much room to tell any kind of a story besides “This is my body,” so we gave Stella more of a story and gave her wraps and things that were beautiful.

I believe she had about 60 or more changes. When we put together the looks, we really wanted to show her as this smart go-getter, this focused professional in the beginning. And then there was this transition that had to happen when she goes to Jamaica and falls in love.

I love the scene where she and Whoopi are together on the bench, and she’s in her striped shirt. It just felt fresh and like vacation. I love the zebra bathing suit cover I gave Whoopi too. And I remember she snarled at me that day, because Whoopi’s not one to want to wear a bathing suit on camera—she’s a big, oversize-T-shirt girl. It was a high-end designer, and I knew it would look great, and it really did. It just took her a while to warm up to the idea.

I felt like I was Stella. And a lot of my friends were Stella. As a professional, going to Jamaica with girlfriends was quite common, and we all had that experience of falling in love with the hot Caribbean guy. So it was clear to me how to bring Stella’s groove back, because I brought my own groove back.

The Wedding Planner (2001)

What happens when a top-tier wedding planner (Jennifer Lopez) accidentally falls in love with a client (Matthew McConaughey)? She stuffs down her feelings at all costs and winds up at a courthouse—set to marry a man she doesn’t love in an attempt to distract herself and please her father. Below, costume designer Pam Chilton explains the thinking behind that wedding dress—which, if you’d forgotten, has been compared to Meghan Markle’s Windsor Castle gown.

Jennifer was trying to play a more dramatic character for her at the time, and that’s reflected throughout the movie in the silhouettes and the turtlenecks and the jackets, like the leather Gucci trench she’s wearing when her shoe gets stuck in the manhole. We also needed her to look professional, like a businesswoman, because obviously the idea of the wedding planner falling in love with the groom is not an ideal, likable situation. So we pushed that this is her job, this is her profession, this wouldn’t normally happen to her because she’s so buttoned-up and professional.

And then with the lilacs and lavenders and baby blues and pinks, that was a very romantic palette that softened her a little bit. We went against that with the red dress that she wears for the ballroom dance with Matthew McConaughey. That was a little fiery. It had a mock turtleneck, so there wasn’t cleavage—it wasn’t showing everything—but between each panel of that drape was a little mesh that gave it a touch of sexiness.

The wedding dress wasn’t supposed to be a big, frilly, princess affair. We pulled a bunch of vintage shapes to get started, and that’s where we jumped off: We liked a piece of this, a piece of that, and combined them all. It’s beautiful, but it’s not a celebration or a joyful expression of one’s self. It’s kind of serious. It’s dutiful. That’s why we liked the vintage feel of that pillbox hat and the veil matching it, because it was a throwback. In the movie, her mom had died, and there was a feeling that maybe this was something her mother would have worn or appreciated.

It was a vintage veil with Swiss dots, and we actually ironed it while we were prepping and all the dots fell off and we needed to shoot. We were like, “Oh, 10 minutes away? No problem.” We cut another veil real quick and stuck dots on. That was only for that quick shot of her walking into the courthouse. Then we had time to refurbish the original and get it all set for her next shot.

I got a lot of texts about Meghan Markle’s wedding dress. I’m like, "Well, I’m sure it’s a coincidence." But she was at a good rom-com age when the movie came out—she could have been watching it at sleepovers!"

Enchanted (2007)

The Amy Adams vehicle follows a princess (Adams) from Andalasia to New York City, where she’s first seen climbing out of a Times Square manhole, and it’s as much a fantasy as it is a rom-com. Below, costume designer Mona May explains how she adapted an animated gown into the live-action fashion extravaganza that introduces Adams’s character.

We needed to create the silhouette of the animated character in live action. So how do you do that? You have to create a giant skirt to make Amy’s waist tiny like it was in the cartoon. It was so much fun, because the 2D animation was almost like an outline—and then when she explodes into live action out of the manhole, there are butterflies on the dress and sequins. It’s so three dimensional.

Amy was such a trooper because the gown probably had 200 yards of fabric and weighed about 30 pounds. The way that it was engineered, the top and the bottom were separate so we could get her out of the skirt without disrobing her completely. (She could go to the bathroom.) We made 11 versions of the dress: one for the stunt woman hanging over the billboard in Times Square, one that we made to look like it was wet when she’s getting rained on, a short dress, like a half-dress, for when she was coming out of the manhole.

It took a couple months because there were a lot of fittings. If the skirt left a red mark on Amy’s hip, it was like, Maybe we have to line it with a soft fabric? We changed a lot of the hoops underneath too because the ones we originally had were heavy. We ended up making them from aluminum, which was a lighter material that could still carry all the weight of the fabric and bounce around in a nice way.

The second dress, her character makes out of the curtains. It’s still very princess-y, but it’s a little bit more grounded. Then we go to the next dress, which is shorter, and then to the final dress, when she decides to stay on earth and be with Patrick Dempsey’s character. She’s stripped of everything. You see imperfections in her skin, the hair is straight, there are minimal details on the dress.

This movie is a journey. When she comes from the animated world, she’s like a cartoon. She doesn’t feel emotions, she mostly sings her words, she has big curly hair and eyelashes. And through this film what we see is her getting real. What are my feelings? Who am I? So the costumes had to support that. This woman you see at the end is very sure of herself.

Love & Basketball (2000)

Monica (Sanaa Lathan) and Quincy (Omar Epps) are childhood best friends and neighbors who share a love of basketball. But on the night of their Spring Dance, their friendship develops into something more (cue Maxwell’s “This Woman’s Work”). Here costume designer Ruth E. Carter explains how she decided what Monica was going to wear on the night she lost her virginity.

Love & Basketball was definitely director Gina Prince-Bythewood’s baby, loosely based on her own story, so we worked together on the arc and how to display the costumes on this tomboy girl who falls in love and climbs out her window to have some time with her beau.

We didn’t have many choices for the dress. The white color obviously signifies that she was a virgin, but this movie wasn’t done with a big budget. That’s why it was important that Gina become involved with some of our decisions, so we could just get to the right thing and not play around.

Sanaa Lathan is such a beauty. I think she was a little bit of an athlete growing up, so it wasn’t a difficult transition for her to put on the uniform and shoot a jump shot. But then when we start [dressing her up], I think Sanaa had to hold back a little bit because her character had to be uncomfortable with it. You see her pulling down the dress, and then when her date goes to get her a drink, she finally sits like the tomboy she wants to be. It’s a really good scene.

She’s All That (1999)

It’s a tale as old as time: High-school jock (Freddie Prinze Jr.) tries to turn high-school nerd (Rachael Leigh Cook) into prom queen—and yes, he has a bet going with his bros that he can do it. Here costume designer Denise Wingate explains how she transformed Laney Boggs’s fashion by the end of the movie, without suggesting that she needed to change who she was inside.

The prom dress was from Badgley Mischka. I had worked with them earlier, and they were still kind of just starting out. They sent me a bunch of dresses and said, "Use what you want and send it back," which was great because we didn’t need it for that long, and it looked beautiful on her. For the rest of the prom, we only used black, gold, and white. And except for the main characters, I bought all the looks from Goodwill. We had to be super creative because the budget was so small, so we repurposed and redesigned.

Rachel Leigh Cook was great about wearing the aprons and overalls. We shopped at thrift stores, and I believe I got the aprons at a restaurant supply store. One thing we were thinking is that Laney has a lot of armor. She’s been hurt in her life. She’s suffering a lot of pain. She doesn’t have a lot of friends, and she keeps this wall up. It was important to show that with clothing.

The prom dress was a defining moment for Laney. But it’s not like she looks so unbelievably gorgeous that you just can’t believe they were hiding her all along. She is still herself.

She also doesn’t care what anybody thinks, at least not to the outside world. She doesn’t care that she’s at the beach in overalls. She’s comfortable being in a bathing suit around all those people, but she doesn’t need to show off. That’s what I love about this movie: Laney is such a strong female character. She maintains her identify. She doesn’t change to please a guy. If anything, he’s the one that changes.

The Wedding Singer (1998)

A movie set in the ’80s has as much potential for fashion disaster as the decade itself, and The Wedding Singer certainly has its share of characters dressed for laughs. But Drew Barrymore’s Julia, the sweet waitress who’s engaged to marry a douche-y rich guy until she falls for tenderhearted wedding singer Robbie (Adam Sandler), isn’t one of them. She wears understated polka dots and pretty florals and an oversized denim jacket. And when she finally walks down the aisle with the right man, her dress is every bit as classic as you’d expect. Below, costume designer Mona May explains how she designed the dress with Barrymore’s input.

It was the ’80s, but Drew’s costumes were always very grounded. She and I are two peas in a pod, and that’s maybe why we’ve worked together since this movie for 20 years, because we get each other. I’m a girl’s girl, and she is as well. I think we’re also very proud women. We want to portray women realistically. She’s minimal on enhancement in any way, body and face.

With her wedding dress, we had to think: What could they afford? She’s not marrying the rich guy now, she’s going to marry Robbie. What’s really her? So we wanted to make it very simple and purposely didn’t make it over-flowery. It was clean, straightforward, from the heart, with a nice fitted bodice and a sweetheart neckline.

Drew was very involved. When we were picking fabrics, she didn’t want anything shiny, she didn’t want any beading. She was like, "We’re starting our life together, there will be a handful people at our wedding, his band will play." She wanted to keep it real.

The Perfect Date (2019)

Brooks (Noah Centineo) gets paid to take a rich kid’s cousin, Celia (Laura Marano), to her school dance, even though the girl has no actual desire to be there. (She agrees to go for her mother’s sake, but refuses to wear heels.) The faux date gives Brooks the idea to create an app where women can pay him to be their platonic escort, and things get complicated when Celia develops feelings for Brooks. Below, costume designer Ann Walters explains Celia’s first look of the movie—and how it compares with the black and gold dress she wears once she realizes she has a crush on Brooks.

The pink dress was originally scripted: "She has on big workman’s boots and a froufrou prom dress." So we found these deliciously lovely velvet boots and paired them with a pink dress that we found at a secondhand shop. I added the pink trim to the dress to help frame her face and give it a little bit more of a pop. And we wanted something that would give her a little personality too, so I added the belt and moto jacket. It really went with the whole vibe of who she was.

One of the great things about the Celia character is you start to learn she isn’t simply rebellious—she’s really smart and strong and unique. She parallels Brooks in that they’re both trying to find their place in this world. That’s one of the things that appealed to me about the film, that it really was just about these kids trying to figure out who they are and be true to themselves.

The black and gold dress is the absolute foil to the first dress. Celia starts having feelings for Brooks, even though she’s trying to deny it, so she tries things her mother’s way. But Brooks doesn’t notice her in the car, and we can tell it crushes her a little bit, that she had put all this effort into playing this part, and she definitely looked gorgeous, but she was a fish out of water in her own skin.

That was actually the only outfit that I did earrings with. She would wear necklaces and some other things, but her regular style was pretty casual, so the earrings were just something to help add to the glamour. I don’t know how much you see of the back of the dress in the film, but we had done a lacing with a ribbon down the back, because the back was completely open otherwise, and I thought she already looked open enough.

Never Been Kissed (1999)

Barrymore plays Josie, an undercover reporter tasked with infiltrating a high school for a story about teen culture. At first, she doesn’t fit in: Everyone called her "Josie Grossie" as a teen, and she hasn’t managed to let go of that persona even as an adult. But over time she gains confidence, makes friends—and falls for her handsome English teacher. Below, costume designer Mona May explains how she created Josie’s final dress, the one she’s wearing when she’s finally kissed.

To Drew’s credit, she really wanted to start out very ugly duckling—and I mean truly. At the beginning of the movie, her hair is mousey, there’s no makeup, she was wearing a suit with culottes, the color is terrible.

But it was great for the character. And we had much more room to play because we went from there to her pretending to be a high school kid not knowing what the high school kids wear, so she puts on this crazy boa with white pants and a yellow lemon bag—it’s totally ridiculous. Drew and I went shopping together, and she would try clothes on in big fitting rooms with everybody. We made the flashback prom dress ourselves. We knew that the kids were going to throw eggs at her, so we purposely picked this fabric that we could basically wipe the eggs off and do another take.

This all led us to the journey of discovery of who she really is, and we end with this beautiful, pink, very feminine dress. It’s soft and pretty, and her soul feels open: Here I am. This is who I am. Are you coming?

It’s custom. We picked the fabric together, added the little ruffle, made a cap sleeve. It’s an Empire waist, knee-length—really beautiful for Drew’s figure. She’s specific about what she likes: nothing too short or too tight. It’s pretty amazing to work with somebody who knows her body so well.

Patti Greco is a writer based in New York.

Originally Appeared on Glamour