‘You Try Driving In Platforms’: How ‘Clueless’ Created The Style That Made It A Pop Culture Icon


Rarely does a year goes by that people don’t celebrate the greatness of Clueless and its impact on pop culture. Twenty years after the film was released, people of all ages still use phrases popularized by the film like “As if!” and “Whatever!” in casual conversation, and we’re willing to bet that there are quite a few people who still reference Monet when it has absolutely nothing to do with art.

But perhaps more than the lines and the actors that delivered them, the clothes featured in Clueless made a lasting impact as well, making it not only a quintessential ‘90s movie, but a timeless cultural juggernaut as well — one that continues to speak to generation after generation. (It probably also doesn’t hurt that the film absolutely nailed the cliques and stereotypes of just about everyone’s high school experience.)

That’s why we wanted to talk to Clueless writer and director Amy Heckerling and costume designer Mona May about the thinking that went in to creating the overall look and feel of the film. We also spoke to actors Wallace Shawn and Justin Walker to learn as much as we could about the styles that were created on a very limited budget for a movie that was almost never made.

You Argued Your Way From A C+ To An A-?

… a lot of the people who liked it liked the world that it was showing and they found that more agreeable than the dog-eat-dog world that Reagan and his followers had represented.

Long before she introduced the world to Cher Horowitz and Dionne Davenport, Amy Heckerling proved that she had a knack for teen stereotypes and comedy when she directed 1982’s “Fast Times at Ridgemont High,” which was written by Cameron Crowe. (She also directed the hilarious and absurdly underrated “Johnny Dangerously,” but that’s another movie for another time.) However, “Clueless” was all Heckerling and like “Fast Times” it was sharp and intelligent, and of course the studios didn’t recognize that at first. Fortunately, Scott Rudin came along and slapped some sense into the film industry. With a small budget and a cast of mostly unknown actors, Heckerling and her friend Mona May set out to create something magical, both in fashion and language, and exceeded everyone’s expectations.

Amy Heckerling, Director: I went to Fox with this pilot I had written, which was just about 20 minutes for a TV show but I liked the character a lot. When my agent at the time, Ken Stovitz, read it he said, “This character should be in a feature,” and he showed it to them. They agreed and I developed it with them, but they had very specific ideas and I wrote a draft and they wanted me to do things to it, and I did and they still didn’t want to make it. Then, when he tried to sell that, because it was in turnaround, nobody wanted it. So, it was very hard. Also, at the time, some youth-oriented movies came out that seemed to be about less intelligent young people and they didn’t do so well, so they figured this movie was just like those so they didn’t want it.

These are movies that I thought were very funny: there was one with Adam Sandler and Steve Buscemi, Airheads. I guess that didn’t perform the way they wanted it even though I thought it was great. And there was also one called PCU, Politically Correct University. It had Jeremy Piven and David Spade and they were great and it was a really cool concept. This movie sounded like those and we’re not making that kind of movie now. Also female, so forget about that. It was in turnaround for a long time till Stovitz got it to Scott Rudin and he liked it. It went from everybody passing on it to a bidding war because people suddenly, what they hate they like. They really stand by it [laughs]. Whatever.

Mona May, Costume Designer: We actually met before Clueless. She was doing a pilot for television about these two young girls living in New York City and I interviewed with her. Right away we hit it off creatively. So, we got to work on this pilot and really fell in love with each other creatively. Just really, really fun. I loved her fashion sense. She’s really well-versed in fashion. And the pilot unfortunately didn’t get picked up but our relationship was formed. She knew I grew up in Europe; I very much have the European aesthetics and more a European sense of fashion. When she did Clueless she called me up and said, “Mona, I really want you to do this movie.” So, that’s how it happened.

Wallace Shawn, “Mr. Wendell Hall”: It was as fantastical as The Wizard of Oz, to me that’s how they looked. I was totally astounded by the stuff that people were wearing. I loved it, of course, but I was totally amazed by it and thought it was hilarious.

Justin Walker, “Christian”: There aren’t many times that you read a script and you laugh out loud at what you’re reading. There were a bunch of moments when I read the script and thought, this is downright funny. And the style, what Mona May brought to it in terms of the style, I mean you’re doing it and you’re in the clothes and you’re like, “yeah, this is cool, I like this.”

Heckerling: We wanted to take sort of what was in the air and have fun with it and take it a few steps further and coordinate what people were wearing. Grunge in the early ’90s, the Seattle influence, had become very big, but then designers sort of caught on and there’s something silly about designer grunge. Just as there had been previously designer punk. We wanted to mock that whole business. The influence of rave culture and dressing a little bit crazier than previously was a call back to hippie times when people felt like the average person could be more creative in what they were going to wear and loosen that whole thing up. You didn’t all have to dress the same, you could get a little costume-y in what you were wearing. Those things had an influence on what we messed around with.

May: Clueless was the first chick flick in a sense. A movie that, afterward you see many of those movies but this was really the pioneering, what Amy did. The fashion was almost like a character in the film. What was interesting for me was translating my love of fashion into the costume designing. Because fashion is really creating clothes for the future—people have not worn it, you haven’t seen it—and combining it with crazy characters in film is really interesting. When you get the script it’s really important to not just dress the characters as mannequins, but they really have to portray the character—who they really are, their characteristics, color palettes, and also you have to work with their bodies and shape and Clueless was really unique in that I was working like a fashion designer and costume designer in one because I was predicting trends.

Shawn: One of the things [Amy] took was slang, which she single-handedly spread to the entire country and the world. I mean, there are phrases and words that nobody had ever heard before that were put into Clueless and became unbelievably popular and some of them remain in the language that people use who have never seen the movie and have never heard of the movie. It’s extraordinary. And, of course, a lot of what is meant to be funny in the movie, including some of the costume design, was not seen as being funny by 14-year-olds who loved the movie. And there were clothing styles that were adopted based on the movie.

Heckerling: It was Mona and it was ideas that I’ve been playing with forever and ripping out pictures in magazine. We knew who the characters were and what their closets looked like. Then I wanted a sort of color palette for the different seasons, so I was driving her crazy because we didn’t have the budget to actually costume everybody. On the call sheets you ask people to bring in what they have in a certain color and of course most of them don’t. Then you sort of are collecting shit and seeing what you could put on people, people in the far background. If they’re in some hot pink outfit that’s killing the shot, somebody has to run out and find something and cover them. You do what you can. You’re collecting stuff from all the places that you get wardrobe from and trying to find what would work and what better outfits work on people that are going to be closer and how to make the background look right.

May: It was completely back and forth. The beginning is really like creating collages, boards for each character, so we all very much contributed together all the ideas. She’s so creative and she pushed me further. I think my work was better because of her. So much of creating films, directors can be male, No. one, not understanding fashion and maybe even afraid of it. And she was completely full on and understood how important fashion is in the film. She has amazing sense of fashion and that is incredibly helpful to a designer on a movie. The collaboration is so much more heightened because of that.

Shawn: I think that even “whatever,” which is now used by all human beings, including me, in sort of every sentence was not really used before Clueless. Except for a handful of kids at Beverly Hills High School, I suppose. There are lots of phrases. If you see it now you wouldn’t even know that some of these phrases were surprising when the movie was made. People didn’t even know what they meant. But you sort of got the idea from the context. To be honest it was very forward looking, not just in the very believable friendships across races, but in the sort of very delightful way that the young gay boy is treated in the film and the respectful and charming way he’s treated. I think that a lot of the people who liked it liked the world that it was showing and they found that more agreeable than the dog-eat-dog world that Reagan and his followers had represented.

May: I really fell into the moment of creating the costumes of the film and working with the characters, being more of a fashion designer. You don’t really think that way. I don’t think when I’m working, “Oh my God, now I’m going to do this and it’s going to influence people.” It wasn’t like that at all. We really were just having such a good time doing this movie. It was not at all premeditated in any way. I really drew from my own sense of style, how I interpreted things. And very lucky, I hit this nerve and I was able to really choose the right things that became timeless. It’s my own sense of style married with this script and Amy’s vision. I think when the movie came out it was an amazing experience to go through, that this movie became such a hit and the costumes became iconic. It’s not what we set out to do.

Is This Like A Noxzema Commercial Or What?

She is just a real bohemian, Earth mother, vegan mommy. She cares more about helping animals than what shoes she’s going to wear.

Before “Clueless,” Alicia Silverstone was that girl from the Aerosmith music videos. You know, the one that every boy in America suddenly had a crush on, as if she had magically appeared on our TV sets from out of nowhere. But when she beat out other actresses like Reese Witherspoon and Zooey Deschanel to become Cher Horowitz, the most popular girl at Bronson Alcott High School, she became an instant cultural icon because of those plaid skirts, thigh high socks, and the hilariously adorable way that she said Haitians. Bringing Cher to life was one of those truly magical movie moments that simply happen because the right people made the right decisions.

May: It really takes almost a year from the beginning for the movie to come out. You really have to be clever, and my intuition and sense of style combined with Amy. It was quite a challenging film because Cher and the girls had about 60 changes each. There’s quite a lot of outfits to come up with and the budget wasn’t that huge. It wasn’t a huge, giant studio film. It was a medium budget movie, so I had to be clever because I couldn’t get everything designer. Also you have to think of those days—we didn’t have computers, it wasn’t like now where you have Instagram and everything and are kind of cross-promoting. It wasn’t really happening then.

Heckerling: When I went to Beverly Hills High School it was just to clarify what I was thinking and see what else was actually going on. In my mind I was trying to do something that wasn’t so absolutely realistic but more of a fantasy of kind of comedy of manners with Beverly Hills in the ’90s as the backdrop. But it wasn’t purely realistic, the way a Fred Astaire movie isn’t exactly capturing the world of the ’30s. Something happier than the way things were or could imagine a different kind of alternate universe. When you go to Beverly Hills High School in the ‘90s even those wealthy people, a big deal of the population there, nobody was dressed in over-the-knee socks and matching plaid outfits and Dr. Seuss hats [laughs]. And certainly when I went to film in the other high school, Grant High School, I don’t think I saw one person wearing a skirt as far as the girls go.

May: It was really funny because that’s really what was happening in schools at the time. When we started the research with Amy and started to looking at locations and going to high schools, basically it was all grunge. It was Nirvana and everyone had baggy pants. Girls were dressed very boyish. There was very little femininity for girls.

Heckerling: I know if you’re photographing people and you have a lot of girls in color coordinated mini-skirts they’re going to look very good. But if you’re going to photograph them in running shoes and dungarees that are schlepping across the ground, not so much. So, it wasn’t exactly what I observed, it was more to see what was going on and if any of that would be useful for what I was trying to imagine.

May: We really wanted to play something very feminine, very girly. To me, it’s almost like a mission in life. I want all the girls to be inspired and be okay with their bodies, and be feminine and pretty. Because I think there’s not enough of that. We don’t celebrate our bodies. We get very caught up in ourselves and what the magazines show and what the consensus is out there of how you should be looking as a female. This movie, to me, was also about being girly, feminine, pretty. It all had to do with these fun accessories, over-the-knee stockings, and the hats and the fun purses, colorful. Everything, also, was very age appropriate. Even though they were high fashion, the girls didn’t look like slight models walking in their little high heels down the runway. But everything looked kind of filtered through the eye of the script. What a girl in high school would wear and how she would incorporate that fashion into her age.

Heckerling: As far as the average student in Beverly Hills high school, not to say that it’s how it is right now or any reflection on the school system as it existed, but I’ve never seen people ignore what was going on. They were so into their own things. The girls were in a constant state of grooming and the teacher — I just felt like, oh my God, what dedication to keep pushing and driving and trying to get through to these people that could not seem to care less.

May: Cher was the Queen Bee, and she was the leader. She really was a girly girl. It was all about looking pretty and very put together, almost matchy matchy. Matching the shoes and matching the purse. It was all about little shift dresses, cap sleeves, cute little empire waist, details of the dresses, flowers, pea coats, berets. The shoes were really important, too, because we wanted to make sure they looked youthful, so a lot of Mary Janes, little platform shoes, nothing super stiletto. Her color palette was really reflecting her sweetness, to the point of even the pen that we created with the little pouf being so girly. Very dainty jewelry. It reflected her inner kindness, even though she was a little bitchy and self-obsessed, through the clothes we wanted to say she was a sweet girl and we learned that she really is.

Walker: Alicia is fantastic. She’s just wonderful. She’s very generous. She’s very kind. She’s very non-threatening. She’s very casual. The irony of acting the role, so here’s my character who at the end of the film is revealed to be gay, right? But the acting of the role, in order to set all of that up, was ironically to set up this sexual tension between she and I. My whole way of building the bridge to the character was to create a relationship and moment as to why I wanted this girl in my life. And a lot of that was attraction-based things so that all of that was in place to then pay off with the discovery at the end.

Heckerling: Alicia was completely there. Once we started shooting she had it down, she knew that character, it just came out of her, which is very amazing because it’s the opposite of the way Alicia is. The good heartedness is Alicia but Alicia could not care less about how she looks during her daily life. She is just a real bohemian, Earth mother, vegan mommy. She cares more about helping animals than what shoes she’s going to wear. I think the main thing is that they’re not made out of animals.

May: Alicia was very young when we did the movie. She was much of a hippie and didn’t really have much experience wearing high fashion. It was a learning process for her, a lot of fittings to get the clothes ready for the 60 changes. We almost had to school her on how to wear the high fashion so she could really become the character. She had to act, she wasn’t really that girl.

Woman, Lend Me Fi’ Dollas.

People were either head to toe designer or they were thrift store or they were 1940s, this was a really new thing.

And then there were the other actors and their hilariously unique characters, like Donald Faison’s Murray, Elisa Donovan’s Amber, and Breckin Meyer’s Travis, who, as legend has it, wasn’t very far off from Meyer’s real personality at that time. Like Cher, each of the supporting characters had a style of his or her own, and a lot of that came from the actors and actresses, because their personalities and talents helped mold the characters beyond just their wardrobes. If the wrong actors had been picked for the roles, it could have spelled doom for the movie, especially since Murray was almost played by a now-beloved funny man.

Heckerling: To tell you the truth, the person I had met with and loved was Dave Chappelle (for the role of Murray that ultimately went to Faison). He was a real kid. But he had some edge to him. You wouldn’t believe him as a little puppy. I wanted Murray to feel like, if he was using urban slang it was not because he knew it, it was because he had studied it. And Dave Chappelle felt like he was keeping it real. Donald had to say he was keeping it real because he was figuring out what was real, then going for it.

May: That was pre-Sean John. Now there’s much more designers doing men’s clothing with that hip hop look, it’s now more high fashion. We wanted to take Murray a little bit further from the grunge, keep him in the cultural African-American hipster look but elevate it to be fresher. So the jeans, then we really didn’t have designer jeans. It looked like he was wearing designer jeans and designer zip-up hoodies or wind breakers. Everything was, of course, oversized.

Heckerling: I wanted him to be a wannabe, a kid that grew up in a wealthy neighborhood and had all the advantages and all the education that somebody who had to be a scrapper could get any piece of the pie.

May: We really tried to punch him up as well. Then some funky shoes—if you look at the movie now it seems so normal. But when it came out boys didn’t dress like that. It’s funny because it wasn’t as popular of using high end and low end. This was all very unique to the film. Shopping at thrift stores and mixing it with Dolce & Gabbana, it was very unique at the time. People were either head to toe designer or they were thrift store or they were 1940s, this was a really new thing. Mixing it all up.

Shawn: My opinion was very much consulted on how I would dress but, honestly, I don’t have a strong sense of myself and I basically dressed the way other people have dressed me. I wouldn’t know how to go into a shop and buy clothes. When the old pair of pants wears out I simply buy a new one that’s exactly the same as the old one. And I don’t really know, if someone says, “Well what kind of clothes would suit you?” Today, I couldn’t even begin to answer it. So I was quite guided by others. But I have, if someone puts me in a costume I do have the ability to say, “Ewww I don’t like the colors. To me they don’t go together.”

Walker: I loved everything I was wearing. It’s not unlike life. If you are wearing things that make you look good and feel good then it translates into how you’re acting, no question. If you are wearing things you know aren’t right and don’t feel right, then you’re not going to bring out your best. They definitely go hand and hand.

May: [Amber] was really written on the page that way, that she was kind of over the top, she thought she was the smartest, coolest. It was really interesting because you can go overboard with the look, head to toe Pippi Longstocking or the nautical look. I really wanted to make sure that she was still stylish, that it doesn’t look like a Halloween costume in a sense. She doesn’t become a complete caricature. It was fun to play with that balance with her. I think we achieved it very well. I still look at her outfits and I love them. I love the Pippi Longstocking outfit, I thought it was so much fun to do.

Well, There Goes Your Social Life.

That’s what’s so cool about being a costume designer, to create and have this follow through on all the costumes, no matter if it’s a gym outfit to a bathing suit.

From a purely fashion perspective, the most interesting scene in “Clueless” has Cher and her friends in gym class taking tennis lessons from Ms. Stoeger, all while wearing ridiculous “uniforms.” You could argue that the scene is owned by Dionne’s dry delivery in her hilarious burn on Amber – and you’d be correct – but this gym class also serves as an example of just how good May and Heckerling were at not only working within their limits, but also making it seem like every little aspect of each character was different from the next girl.

Heckerling: I don’t know if you noticed but in the beginning it’s fall and people are wearing the color of what we used to call fall foliage colors. My parents used to take us on a trip in the fall to go a little bit out of New York City and see all these trees and they’re gorgeous. It’s reds and yellows and oranges. I wanted to feel like that beginning, that fall, that crispy leaves are changing kind of feel. So, Stacey is in the black and white with red, Alicia is in yellow, and I tried to get as many background people in those colors as we could deal with before the sun goes down. Then when it was Christmas we used a lot of the Christmas colors, the reds and greens and then when it was spring, when Christian comes and everybody’s looks turn to love, I had Easter pastel look—Easter egg kind of feel. Using that, then I thought, okay, but they’re cheerleaders throughout. They have to work for each season.

May: Me and Amy wanted to make sure it looked like a gym. It’s usually some black and white uniform, so we riffed on that. It was really fun to do that, to riff on the gym outfits for each of the girls. There was Amber with the stripes and we did these little water holders, which at the time they were not even on the market. We just created them with the prop people, which was really funny because later Karl Lagerfeld had them on the runway in his next show.

Heckerling: Gym clothes, it could be in the fall, winter, whatever, so I figured the cheerleaders and the gym clothing would be black and white. It would be neutral through all the seasons. Also I love black and white. When I was in PE in high school we had to wear hideous outfits and pantaloons, and I just thought it was the ugliest thing a person could be dressed in. So, I thought it would be cool just to have parameters, it had to be black and white, you had to be able to run in it. It had to be short. But other than that there would be some freedom, looks for everybody. I think I had heard of some school somewhere where people just had to wear shorts and a T-shirt or something like that. You could wear all sorts of stuff as long as it’s that.

May: It’s like the creative expansion of each of the character to have a really fun expression of the gym outfit, for each one of them. We heightened the reality. We really created something different that almost nobody does. We go as slobs to the gym, “Ugh, I gotta go to gym, I’m feeling fat, I gotta cover myself.” So, it’s more of a baggier T-shirt. In the whole film we took something very mundane and very every day and made it a fashion statement.

Heckerling: Also, I’m very influenced by the movie Cabaret. When you see the girls in the chorus and they’re all wearing the over-the-knee stocking, which was like slutty look of the ’30s but with shorts and crop tops and stuff. So, there was a consistency but they were all different. I thought that was very cool.

May: It’s interesting to do movies like Clueless because it’s so easy to get stuck in a certain period. You can say, “Oh my God, the movie is from 1995,” but I think that it’s transcendent, it has transcended time. Somehow I was able to very uniquely play timeless fashion that is, even now, some of the outfits that Cher would wear in the movie, now you could totally go to the streets of New York or Los Angeles or Berlin and it would be cool.

Do You Prefer Fashion Victim Or Ensembly Challenged?

To be a rather agreeable, even nice, human being was a thrill actually. Absolutely fantastic.

By the time they were cast as Mr. Wendell Hall and Miss Toby Geist in “Clueless,” Wallace Shawn and Twink Caplan were show business veterans. Their young castmates were mostly newcomers or had very little experience in Hollywood, but when it came to the fashion aspect of the film, everyone was in the same boat. In fact, as May and Heckerling were tearing apart their creative boundaries in developing the looks for Cher and her friends, they almost had to work in reverse to create the teachers’ lack of style while still making them seem lovable and sincere.

Shawn: I thought it was one of the greatest scripts ever. Of course in real life I had been a school teacher and this was a very well-meaning teacher. Often in films the teacher is a sadist or an idiot. In this case he’s quite sensible and sincere. Trying to do his best and the romance is charming. He’s a rather shy person perhaps. He needed to be fixed up.

Heckerling: Miss Geist was based on my English teacher in high school and she was the one who told me, “Forget about art, you’re going to be a writer.” She meant a lot to me, her name was Ms. Rosencrane. My girlfriends and I used to look at her in English class and she would be wearing these sort of hippie-ish house dressy flimsy dressy dresses. She always seemed sort of frazzled. Her makeup was going all over the place and her hair was a mess and she had these little glasses but they really magnified her eyes. She was just begging for a makeover and my girlfriend and I, Ruth, we used to draw pictures of what we would do to her to make her look better.

May: Everything is important, from the main character to the last extra. We spent a lot a money dressing all the kids in high school, they were part of the film, because even then the clothes were great. Everyone was just head-to-toe, they were given hats and backpacks and jackets and pants. You had to go all the way down from No. one character Cher, Dion, Tai, Travis to everybody all the way down to this one extra who’s going to be part of the classroom. They have to look like part of the film.

Shawn: Mr. Hall is a wonderful character and I have played a lot of very strange, creepy parts. Sometimes people who are not even human. And, of course, I’ve done a lot of animals with my voice, so to be a rather agreeable, even nice, human being was a thrill actually. The teachers actually are good people who are setting an example. Or if you want to look at it a little differently, the teachers, they’re sort of out of the ’60s and they may be a little bit less materialistic and a little bit more concerned with the good of society than the young people who are the students. Because the students have grown up under Ronald Reagan and they’re more into, let’s say selfish concerns. Certainly they’re into materialistic concerns. And the film is very friendly about people who are mainly interested in clothes, but it offers some alternatives.

May: The teachers had to look great and it was so much fun working with Twink creating this Miss Geist character, who in the beginning was very un-put together with the lipstick and the run in her hose. One of the outfits that I made for her, the shirt collar was almost too big, so it made her even smaller. Then progressing her to getting more and more put together as she’s falling in love with Wally Shawn’s character, it was really fun to show the transition for her.

Shawn: Mona May and Amy are clothes experts. They thought of very, very delightful costumes. Of course, I’ve been in some films where people intentionally try to make me look funny or horrible and I find that a little upsetting. But I knew they were trying to make me look good, so I could only be delighted. There are certain things, because I’ve been a short actor for many decades, I’ve never grown any taller and never have been taken very seriously, there are certain things that I’ve seen before. When the costume designer says to me, “Well, we thought it would be funny if you wore a bow tie,” I’ve seen that 7,000 times. I usually say, “Well I don’t want to wear that,” because I’ve already been down that road. I know what that’s about and I don’t want to look like that.

I Was Just Totally Clueless.

(L-R) Amy Heckerling, Alicia Silverstone, Mona May
Getty Image

(L-R) Amy Heckerling, Alicia Silverstone, Mona May

Why can’t the world be more like that high school?

Just how cemented in pop culture is “Clueless?” Twenty years later, Heckerling is working on a version for Broadway. This is great news, because Heckerling assures us that her film will never be remade. “The story is told,” she says, but as a musical it can be told in a brand new way, and we can most certainly expect to see some familiar faces come back, if only for the sake of celebrating this unique film. One person who is definitely coming back is May, because there’s no way that Heckerling was going to let anyone else even try to match her fashion brilliance.

Heckerling: I’m working on the musical for Broadway, hopefully, God willing [knocks on wood] and it’s got the producer from Jersey Boys and the director that did Rock of Ages.

May: Amy asked me to do it and I’m so excited, I can’t wait for when the time comes and I get to do work with her and create new looks, reinvented and updated in a new way. Also it’s a different medium, working on a different scale, it’s a theatre. It’s going to be really fun figuring it out and we have to reconsider certain things because they’re iconic, and update some things.

Heckerling: It all seems very crazy to me. When you start thinking about time, how many years this is to how many years that was. I was just watching a rerun of The Monkees and during one of their musical numbers they cut to footage of 1920s people dancing, crazy Charleston stuff. So, you think the mid-’20s to mid-’60s is 40 years. What was 40 years ago from now? The ’70s. But do you look at Last Tango or Cabaret and say, “Oh remember those creaky old movies?” or The Godfather? And yet it was like an entirely different universe from the ’60s to the ’20s.

Walker: Your instincts tell you what you’ve just done is good but you never know until you see it up there on film, and then what the movie became and what it became to now a third generation is mind boggling. I mean, there are the people who saw it when it came out. Then there are the people who saw it, like the new millennial kids that saw it. Now there are like the children of the people who are my peers who are now watching it. It’s just incredible how it appeals to what I think is a third generation of people.

May: I’m very proud of the film and I learned a lot. I think it prepared me for the other films I did in the future. Because after that I could do almost anything. This was really, really difficult and I kind of became the go-to girl for female films and it was really fun. I got to do Never Been Kissed, Romy and Michele, Wedding Singer, which perpetuated my own style. Having fun with clothes, being more fashion forward. I have a very specific color palette that I work with, very bright and peppy. It’s really important to me because I think color’s emotional and we react to it. It really can paint a story with color.

Shawn: Go back and look at all the movies that came out in 1995 and before that, there was something special about that. It’s a very un-judgmental movie. Of course, some people could be shocked by the romance of Cher and her stepbrother. Even the treatment of the divorced father is done with a very light touch and is very charming.

May: I think that’s why the movie’s still relevant, for [people] who are into the movie, they get it. I think now it’s even more apropos to how you dress. And with Instagram, everyone knowing the designer, kids really are so much more aware of fashion and designer names. The movie is really right on now because this is how everybody really looks at fashion, they know everything. I was at a Clueless screening at the Hollywood Cemetery two years ago, the outdoor screening they have every summer, and there were teenage girls running around in Cher’s outfit and Dionne and Miss Geist. They weren’t even born when the movie came out. I think they even get it more so than any of the other generations because they really are so much savvier and exposed to the high fashion. For them, dressing up for gym is cool, I get it.

Heckerling: It wasn’t so much, well, here’s how the ’80s were and here’s how the ’90s are. Fast Times, Cameron Crowe was in high school for a while studying the kids and that was all very real, and that’s what hit me when I read the script was there was no bullshit in it. You knew those were real people and those were real events. Then you could play around and try to make things funnier or whatever. But it was not people saying, “Uh, here’s what it must be like in high school.” There was nothing older about it. It felt like it was coming directly from the young people.

Walker: It’s not easy to create it. A lot of people try, but to create something that holds up over time and doesn’t become dated is a miracle. It’s miraculous. Why? Why does this movie that’s set in the early to mid-90s resonate 20 years later? Because it’s not just of an era, it’s of its own era. It created its own genre. If you watch it, almost nothing about it is dated. The kind of tone we were using, but the clothes and everything speak for themselves. The dialogue, the characters, the relationships, the comedy. That was all timeless.

Shawn: I suppose I would ask why can’t every working experience be like that? Why can’t the world be more like that high school? Because I’ve been in a lot of movies before and since that one and each one has its own atmosphere, its own rules, its own feeling. This one was very special.

May: I’m extremely proud and I cannot tell you how much joy it brings me when I meet people every day who find out I’m the designer and go, “Oh my God, I love Clueless! I saw the movie when I was a teenager and I made my parents buy me the Jeep,” all this crazy stuff. It’s so cross-cultural because I can meet someone in their 40s who was a young woman then, and I can meet someone in their 30s, and then the teenage girls, the Rookie Magazine readers who still love Clueless. Straight women, gay men, it’s everybody. It’s great and incredibly satisfying.

Walker: I know the character I played was important. My life has moved on, I’m involved in other businesses, but I enjoy talking about it because it was very meaningful to me at the time. I know how important my role is to a lot of people.

Shawn: Clueless really shows a world that is somewhat nicer than the real world. Maybe something we would aspire to. Something that would be better than what we have. And it’s quite pleasant to live in that for a while.

May: When I die I’ll have a graveyard and there will be a pink boa. Something very fun, I’ll be remembered forever. I love it.