Amy Heckerling On Set Amy Heckerling On Set

The Review/ Interview/

Amy Heckerling Explains Clueless’ Iconic Style

Do you prefer “fashion victim” or “ensemble-y challenged?’

Oct 7, 2016

Clueless is 21 years old but head into any Forever 21 and you could swear that Tai, Cher and Dionne were going on a shopping spree. Amy Heckerling’s incredible 1995 adaptation of Jane Austen’s Emma, which traded Regency England for Bel Air and prudency for makeovers, is the one of the greatest comedies of all-time. It’s also pure eye candy for any woman who appreciates a beret, plaid miniskirt, over-the-knee socks and platform mary janes. We talked to Heckerling via telephone to discuss her collaborative process with her costume designer Mona May, her favourite outfits in cinema and why rave culture was a pivotal inspiration for Dionne’s hatwear.

Clueless screens at TIFF Bell Lightbox November 15, as part of TIFF’s fall “Fashion & Film” series in partnership with Nordstorm. If the idea of salivating over the clothing in films like Romeo + Juliet, La Dolce Vita, Bill Cunningham New York and The Royal Tenenbaums appeals to you, head here to buy tickets now.

When you were writing Clueless, did you have certain outfits in mind?

Well, part of it was that I was going to have a lot of girls talking and joking around. And I thought they could be making comments about other people's clothes, so it was woven in a little bit. Of course, when you first write something and then it actually gets made with the actual actors and the clothing is there... that all changes. So you're always trying to come up with new things to say.

What were you inspired by, aesthetically?

Clothing is a strong indication of a person's character. And you're making fun of the times. Let's see. Cher's first outfit, the plaid suit with the yellow? I thought about the fact that her and Dion are friends, so they might go shopping together a lot. And they might be into some of the same styles, or see the other one looking good in something and get something similar. The fact that they're both wearing plaid is a take on grunge because that was very big in the ‘90s. The true grungy people were wearing plaid because those shirts were warm and it started in Seattle. There was this sloppy, devil-may-care way to throw a shirt over another shirt and be warm, but the plaid became sort of trendy. We thought it would be fun to make an upscale fashion version.

It's almost like a Chanel suit, but done in lumberjack fabric instead.

I always liked that incongruous fabric in a style you wouldn't think of. But I'm not a fashion designer, so my ideas just stay in my head.

The over-the-knee socks, that was something I always loved from silent films when women would wear the stockings and they would be rolled up at the top? And then in Cabaret, there was a take on that with the Liza Minnelli outfit. I thought that was just the hottest look that could be. They briefly became in-style in the late ‘80s. Actually, Kirstie Alley has them in the hospital scene in Look Who's Talking. I wanted to use them and Mona May who was the costume designer and I conferred about it. She said, "it doesn't matter if they're in style, or out of style. We'll put them in and they'll be in style."

Clueless Suit

Where did Dionne's Cat in the Hat hat come from?

There was a rave movement going on in the ‘90s, with mind-expanding drugs and glow sticks and wacky clothing. It was a reboot of the hippie movement because people would be very creative and come up with their own ideas of what they wanted to wear. You know, if you went to a place where everybody was on ecstasy and they would just go on and on and on… People were wearing very bizarre, different kinds of outfits that weren't dictated by the fashion industry. One of the accessories I noticed a lot were creative hats that reminded me of Cat in the Hat. And I thought, "Well, that would be good to do a stylish take on that." Mona found that hat and she was just crazed for it, she loved it. Mona May has an expression which is that you're not completely dressed until you've found the right hat.

I would sit in on classes and visit different high schools. Most kids would throw on pants and a shirt and they were dressed. If you look at any Hollywood movie, there were many, many more layers and accessories that the designers throw on everybody. So a person wearing a sweatshirt and jeans turns into a person with a t-shirt and an overshirt and a jacket. We tried to be more, not realistic but more creative in terms of not just piling stuff on but making it say something. Like the fuzzy backpacks that were very tiny. Usually a big bag needs to be a backpack to balance the weight. But a small one is kind of a funny statement. And the fact that they were whimsical, that they were shaped like stuffed animals, was saying, "No, it's cute. I'm wearing something childish." When you're in your teens, it's not that far away from your childhood. So it's a yearning for the past, but also a fashion statement.

It's the same with the feather pens. It's like a quill, but done in this poppy, super ‘90s way.

And that's not far from the Trolls with the fuzzy hair, which kids used to like decades before that. There's always a fuzzy, cute thing to play with.

__I wanted to ask about how you styled Stacey Dash. The film still feels so ahead of its time in terms of having Black leads and this other world that Cher is a part of and intersects with. __

I originally wanted Stacey to have a different hairdo for every outfit. I thought that it would be so cool if for everything they wear, they're thinking about the entire look. They would have a different nail colour and a different hairdo to go with the rest of the ensemble. But her weave was just so... time-consuming. We could move it around into different shapes, but we were locked into it. She was always trying to lay her head down, it was heavy.

Were you looking at specific hip-hop and streetwear styles as well? There’s so many different subcultures referenced in the movie: grunge, skateboarding, ska and swing music.

Well, I'm looking at all the fashion stuff when I'm getting ready to do a film. Whatever you wear says something about you. And we were going to a lot of classes and schools, seeing what people were wearing in the clubs. Seeing whatever everyone is wearing all over the place. There was a bit of a resurgence of the Rat Pack... that was a brief glitch in the ‘90s. And I thought that was really interesting because if a character was looking to stand out and be different, or just searching for what he likes... he might look to different time periods. To the music of Cab Calloway and Benny Goodman, as opposed to Coolio and Third Eye Blind. That would be a different kind of character who would wear a different kind of outfit.

__Obviously, Cher has an incredible arc in the film. How much did her outfits outline her transformation as a character? __

Well, I didn't really want to change her mode of dressing as much. Just out of necessity when we see her at scenes at the end, she's wearing pants to go see the skateboarders and when she's talking with Josh at the end. When she goes to school, that's more when she gets all dressed up. And certainly when she goes to the wedding, that's dictated by the bridesmaids and what they have to wear.

__I love that dress at the end and how she wears her hair. __

She looks really pretty. I mean, fortunately, it's a wedding, it's spring, it's very light and pastel-y. But Alicia certainly has the colouring to look fabulous in that kind of an outfit.

Is there an outfit that was your favourite, one that you think is just perfect?

The yellow outfit for the first day of school resonates with me. Mona May had one outfit that I thought looked really cool. But she said, "I can't sleep, I've been losing sleep, this isn't it. It's the first day of school, she's got to really pop." She finally hit on the yellow, which not many people can pull off but Alicia can. And then she felt like, "Okay this is the outfit that will stand out." And she was totally right.

__The film has such an influence on fashion. Today, you go into a Forever 21 and all the clothes look like they could be in Clueless. Obviously, not as beautifully tailored or as well-executed… How do you see Clueless’ impact on popular culture? __

I do it and I move on. I don't think like, "Oh, how much did I shape the universe?" I'm glad if people like it because I was trying to make everybody look good, but at the same time express who they are. I don't particularly think those low-riding pants look good on everybody. I was very happy when Justin Timberlake decided to bring sexy back and wear a nice suit. You're making fun of some things, you're playing around with others… Upgrading or accentuating what's funny about something. It's all for the purposes of the film.

Clueless School

Do you feel that costume should always be a function of character?

It's so many things. You can have an extremely worked out vision of what the character is and what they wear. Then, the actor comes in and because of their colouring and their body type, you have to throw it all out and start over. If I said "I'm going to make a movie that's all pastels and look like the land of Easter eggs," and John Travolta comes in with his dark hair and pale skin that looks so great in blacks and reds and purples, you're gonna have to change things.

Is there an outfit in a movie that you always think about?

Cabaret. Liza Minnelli in “Auf Wiedershen,” when she's got the black shorts with the over-the-knee stockings and the derby hat. I think that's as good as a person can look. Actually though, the competitor would be Ann Margaret in Bye Bye Birdie when she's got the pink ruffly shirt and the pink capri pants. I think that looks pretty fabulous. There was a movie that I don't think people know that well… The French film The Tall Blonde Man with One Black Shoe. There was an evening gown a woman wore. She was very slinky and beautiful looking, and it was very covered up with long sleeves, high neck. Then she turned around and the back went right toward the crack of her ass and it exposed a little bit of it. It was just such a shock. I mean, I wouldn't want to go around wearing it but that woman with that kind of a reveal was very cool.

Black shoe

As far as men go, George Chakiris in West Side Story when he went to the dance in the black skinny suit? With the purple shirt and the purple socks and the purple lining of his jacket? (Laughs) I just thought, "Oh man, that is so cool. It's all black and purple and the purple is in every place that could be a reasonable place for it.” The way he danced and looked in it was just amazing.

What are some of your favourite movies where you just love the world they create with the clothing?

I don't know. I mean, I like old movies.

I love Sabrina. That Givenchy ballgown Audrey Hepburn wears is so beautiful.

Well, Audrey Hepburn can wear an outfit, that's for sure. When she's the beatnik in Funny Face, very simple. Black turtleneck, black capri pants, doing that coffeeshop poetry kind of dance...

A lot of Fred Astaire movies where it’s what Ginger Rodgers is wearing. Not the big feathery things, but the tight gowns where you see the criss-crossing straps in the back are very cool-looking. Oh! Mae West. I forget which one, she's on trial and she's also defending herself. (Note: The film is 1933’s I’m No Angel.) And she's wearing a lace, like spiderweb kind of… (Laughs) Oh my god, who would wear that at a trial? She's got a great sense of humour about fashion.

There are so many outfits in Clueless that are burned into my brain forever as this standard of how beautiful someone can look. The red Alaïa dress that Cher wears! And she's got the matching coat with all the feathers around her neck and the shoes that are dyed to match.

That was based on something that happened to a person I didn't know, but people told me about. He was held up and his wife had recently gotten him a lot of suits because he was usually a slob. And he was being very very careful not to mess them up. And he was held up at gunpoint and the guy told him to get on the ground. And he hesitated and he said, "But this is an Armani." (Laughs) He was more afraid of his wife being mad at him for ruining the suit, than the guy with the gun.

I thought that reminded me of a joke of Jack Benny's. You know, "Your money, or your life.” When he responds, "I'm thinking?" I needed something would sound like, "Oh, this is a big important designer." But the crook wouldn't know who it was. So actually, Mona found this Alaïa and that was perfect and it looked great on her. And then she made that coat to go with it.

__Also, that brown dress that both Cher and Amber wear that has that ribbon around the waist? So perfect. __

Yeah, it's actually a cranberry colour because it's Christmas so everybody's wearing red and green. That actually wasn't an expensive dress. But they both looked great in it and it went with the theme of Christmas colours.

The white Calvin Klein dress that she wears to go on her date with Christian.

There was a whole trend of slip dresses. And so, I thought that would be good to anger her father because it looks more like underwear.

You also do so many things where you layer something transparent over something else. I think of the outfit where Cher’s doing her driving test...

Well, I figured she would want to look good. Because people tend to be more accepting of people that look good. And if you don't look good, they tend to write you off more easily. And so, she would make a real effort. But her idea of what a real effort would not necessarily be very mature. And so, we wanted to make it kind of frivolous but look like she was trying hard.

Your film Fast Times at Ridgemont High also has so many iconic outfits. Like Spicoli's Hawaiian shirts, his checkered Vans.

I forgot the name of the designer, she was wonderful. (Note: the costume designer was Marilyn Vance.) She spent a lot of the time at the schools and at the beach. That was a very different way of working that was based on Polaroids of real people. We would do what we could to make the girls look attractive. There was still a ‘70s influence in the styles of the time of fall sweaters and patterns and things. What I really liked was having fun with the uniforms of the fast food places. So you know, one guy has to wear a tuxedo but it shouldn't fit him well. He should be floating in it. And the other ones, they were like candy stripers. They were young working girls, so I wanted them to look like little nurses. And the shoes though, the iconic checkered Vans — that's purely Sean Penn. He found those and he said, "What do you think?" And we all went, "Yeah!" That was that.


That is so cool! Oh and Judge Reinhold, so depressing. That pirate outfit that he has to wear.

Well, we wanted his work clothes to get lower and more embarrassing.

Do you find that your approach to fashion is also influenced by what you see in cinema?

My approach in dressing people or myself? (Laughs) Well, sometimes I forget what year it is because I watch old movies. But I've given up on shopping because it seems like there's nothing new and I don't really care. When I have to dress people, it's different. Then you deeply immerse yourself. And I'm always ripping out pictures of stuff that I think looks good. So I've got folders from different decades. But for myself? I know what my body type is, so if they say "wide pants are in style," or "high-waisted pants are in style…." I'll go, "Well I don't care." I'm wearing what looks good on me. I'll wear the jeans that fit my body type and a black shirt, or a hoodie if it's cold. And that's that. You won't ever notice me.