How Mona May Turned a Fashion Degree Into a Career Costume Designing Iconic Films Like 'Clueless'

"It was really fun to have the opportunity to marry two of my loves," says the designer behind "Romy and Michele's High School Reunion," "Never Been Kissed, "Santa Clarita Diet" and more.

In our long-running series, "How I'm Making It," we talk to people making a living in the fashion and beauty industries about how they broke in and found success.

Beverly Hills BFFs Cher and Dionne in "Clueless." The goofy late bloomers in "Romy and Michele's High School Reunion." The endearingly awkward Josie "Grossy" Geller in "Never Been Kissed." All of these characters hold a special place in our collective hearts. After all, they made us laugh, felt so relatable during our formative years and influenced the way we dressed — back then and today.

It's nearly impossible to think of Alicia Silverstone's Cher without her yellow plaid skirt suit, Calvin Klein slip dress and luxury wardrobe organized via a fantastical computer program that Silicon Valley still can't replicate in 2019. (Also, how many of our younger selves learned who and what "an Alaïa" was from the 1995 movie?)

A mention of Romy and Michele immediately brings "business women" power-shoulder suits and pastel Lycra mini-dresses to mind. And I'm still hesitant to wear white jeans, in general, after Josie's first day of senior year debacle. These films' fashion-referential costumes are such integral parts of the characters — and of why we still love them decades later — and we have designer Mona May to thank for the sweet, sweet nostalgia.

"That was the '90s — there was no Style.com," explains May over the phone from Los Angeles about the groundbreaking fashion influence of "Clueless" that still resonates to this day. "There was no Instagram or influencers. I was like the original influencer. That was so fresh at the time."

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She has the skill to translate bonafide runway trends into character-developing (and joke-supporting) costume — cementing both the story and style into our collective consciousness. "My assistants coined this phrase 'Mona-fied,'" laughs May. "It goes through my eyes and the eyes of the character and then it becomes real."

Her talent and enthusiasm for fashion dates back to her childhood. She recalls designing outfits for cut-out paper dolls and dressing her friends and family at the age of seven. May's international background — born in India, raised in Warsaw and Berlin and studied in Paris and New York — also gives her an insightfully global outlook on fashion and style.

May booked her first official costume design gig in 1989 for the MTV comedy series, "Just Say Julie," written by and starring Julie Brown — who, fun fact, also played exasperated gym teacher Ms. Stoeger in "Clueless." From there, May has placed her fashion-forward stamp on the big and small screens: L.A. nightlife spoof "A Night at the Roxbury" (shiny suits and man jewelry!), Amy Adams as a Disney cartoon princess come to life in "Enchanted," the television version of "Clueless" and the Whitney Houston TV movie biopic, "Whitney." She's constantly challenging herself, too, incorporating live action with CG or animation — or both — in "Enchanted," "Stuart Little 2" and Eddie Murphy's "The Haunted Mansion."

Notably, May enjoys a 20 year-plus collaboration with actress/producer Drew Barrymore, starting with '80s-inspired looks in "The Wedding Singer," turn-of-the-millennium 'fits in "Never Been Kissed," of course, and three seasons of SoCal style in the zombie comedy series "The Santa Clarita Diet."

Considering "Never Been Kissed" turned 20 earlier this month — and the latest season of "Santa Clarita Diet" just dropped on Netflix — it's the perfect time to catch up with May and learn how studying fashion led to a career in costume design, her special balance of envelope-pushing style and memorable storytelling and why she loves working with Barrymore.

How did you start your costume-design career?

I studied fashion in Europe and in New York and ended up in Los Angeles at the Fashion Institute of Design And Merchandising (FIDM). I had friends at USC and UCLA film school and they were like, "We're doing our little movies and you're in fashion, can you help us?" This was the moment that everything changed, because once I figured out you can work with a script, create a whole entire world, figure out the characters and create a life for them, it was quite addicting. While in school, I started doing music videos and commercials. It was the '80s and MTV was starting up. I started working with MTV on "Just Say Julie." It was really fun. Weird Al Yankovic and [celebrity guests would] come on. We were making clothes and costumes out of nothing.

Which project would you consider your big break and why?

It was definitely "Clueless." I met [writer/director] Amy Heckerling on a pilot, which didn't get picked up, and we fell in love with each other. When she wrote "Clueless," she said, "This is the movie for you." She knew I had a fashion background and I grew up in Europe; she wanted something very fresh and different than what was on the streets at the time. It was grunge. We went location scouting to some schools in L.A. and it was just quite dismal. Everybody was in baggy pants, flannel shirts. The story was about these beautiful girls that lived very affluent lifestyles in Beverly Hills and had everything that anyone could ever imagine — money to buy clothes, travel to Europe. It was really fun to have the opportunity to marry two of my loves: fashion and costume design.

In "Clueless," the costumes are another larger-than-life character. Same with "Romy and Michele" and so many of your other projects. How do you find that perfect balance between fashion and storytelling through costume?

You always want to start with the character: Who are these people we are creating? In "Clueless," the most important thing for Amy when she was writing the script: she wanted to make sure they are girls. They are not fashion models. They're not strutting around in heels on the runway. It was really important to translate all the trends coming out on the runways into the world of teenage girls and the characters to make them real.

Cher had her own color palette and silhouettes. The A-line dresses, plaid skirts, cap sleeves and empire waist dresses — everything was very sleek and feminine. Dionne was much more avant garde. Her skirts were shorter. There was vinyl, leopard, bright colors. She was always pushing the envelope. You could read who they are through the fashion, but also who they really truly are as characters. Comedies are interesting because you can overpower the actor with the costume very easily.

You often illustrate the jokes and supporting physical comedy through costumes. What is your approach to finding that balance?

Filmmaking is such a collaborative experience. You sit down with the director and go over the script and try to figure out who these characters are and what makes them tick. What is the journey they're going through and what are the the high points? Or where the comedy has to pop. That's when everything starts gelling together.

Actors are so collaborative, too. They have an instinct. You can conceptualize a lot with all the research, the boards, visual stuff you present to directors, discussions with the production designer. But it's not really until you're in the room with the actor, in the fitting, when the true magic happens. In that moment, you have the actor's body, you have their physical expressions, how they move. You're putting the clothes on them, [and you see] how that gels and you know how far to go, how funny this could be. Because you can put the same sweater on two different people, but it's not going to have the same effect.

Drew is really a great example because she gets into it. When we did "Never Been Kissed," we went shopping together and we were trying all kinds of different ideas. This whole boa thing was so great, when she goes to her first day of high school. I mean, why? She really wanted it because she wanted to trip on it. Also, the white jeans, when they spill the chocolate, the bright yellow lemon bag, all the details. You prepare for it, but really in the fitting, when the actor is in the right thing, you feel it. They feel it.

"A Night at the Roxbury," too. I love that movie.

Comedians are great to work with. Those guys [Will Ferrell and Chris Kattan] were insane. They were constantly moving. I was trying to work and they can't even stay still, [which also influences] how I have to make the clothes. The suits have to stretch, because they're constantly making their crazy moves. [The environment also] dictated the colors. The movies happen at night, so they have to be shiny and you have to see them at the club.

I get a lot of questions about Alicia Silverstone in the yellow suit in "Clueless." It was so important for her to pop in the quad when we open the movie. We tried blue; we tried red, which is a sexy color. But truly not until the yellow, it was like, "Oh my God, this is it. Look at how perfect it looks on her." The color looks great in a quad against all the green. It's one of the most memorable outfits from the movie.

You've worked with Drew Barrymore for over 20 years. What was a moment you had with her on your recent project that made you realize you've both come full circle in your collaboration?

It's the ease of working with someone. I know what's best for them and they have complete trust knowing that I will find that — that I can really see them — and I will choose the right pieces. That kind of trust is really important with any actor and to have that for that long is really special. There's a lot of comfort in the fittings and conceptualizing — and we really get into it.

This was an interesting character because we had to go from a dowdy housewife in Santa Clarita to someone who's really empowered now — by eating humans — and self-confident. She's starting to wear designer clothes. Her look is completely different from season one now to season three. It was a great arc that we're able to create together. Drew is very involved in the details and colors. She brings ideas now from Instagram. It used to be tear-sheets [laughs]. It's really fun to be able to collaborate in that way. It's like family.

You also do a lot of streaming and TV series and pilots. What are the biggest differences between costume designing for movies versus episodic series and how do you switch back and forth?

Well, movies are my first love. It's an epic kind of adventure when you have time to prep, collaborate with other departments and think on the script and how to create the characters. You have time to dive into details much deeper with actors. With TV, it's a very fast-paced medium. You don't have a lot of time to prep. You have to be always on your toes. It's interesting going back to TV because it taught me to do things and make decisions faster. Lucky that I've been doing this for so long. I trust my instincts 100%. It's really a whirlwind. I agreed to do this with Drew because I had that connection with her, so I knew we could do it.

Looking back over your career, what was one memorable learning experience that you still use today?

One of the most challenging jobs was "Enchanted." Those are iconic fairy tale characters that live in people's psyche and [I had to give] them a little bit of a makeover and bring something fresh. The other challenge was working with 2-D animation. The characters came from completely old-style Disney animation and then [I had to] translate that into live-action costumes. Because 2-D animation is like a drawing, a flat thing. There's no gravity. You can do anything you want. You can put a tiny little waist and giant sleeves on a character and everything's going to bounce perfectly.

Then you have to make that costume for Amy Adams, who's going to run around Times Square. She's going to get wet and hang from a billboard and how do you take the 'princess,' animated proportion to live action? You have to make the skirt super huge. How do you make sure the actor can wear it? She was such a trooper. That skirt was made from over 200 yards of fabric, so it probably weighed a minimum of 25 pounds.

In the case of Queen Narissa [Susan Sarandon], the costume and character had to morph into a CGI dragon. So it was 2-D animation to live action to CGI. It's not just technology and how do you deal with all of that, but taking the design and making it work in all the different mediums. Those are the moments of the future of fashion and predicting. This is a whole another part of designing. It's like invention. How do you find something new and fresh?

Where do you see your career progressing in the next 10 or 20 years?

I love to teach. I'm huge on mentoring young designers. I work with a few schools in Los Angeles to meet with a group of young designers every month. I just help them out, encourage them and inspire them. I would love to continue doing more of that. I'm writing a book that will bring a lot of inspiration of what we talked about. We need to inspire young kids. We need to make them believe each of our stories and how we see something as unique. Just believing in ourselves as artists is hard. We get discouraged. There's a lot of competition. How do we really find our voice? I will continue making movies, hopefully working with my beloved actors and directors, as I have over the years.

What advice do you have for aspiring costume designers?

We have to, number one, love what we do. That really is key because this is not an easy job. We work long hours. We go away from our families on location all the time. Now more and more films are being filmed away from where we live. You have to be really passionate about this so it doesn't feel like work.

All those details — showing up, being professional and all this stuff — are really important. Just get your hands dirty and assist and intern. Reach out to costume designers if they love their work and say, 'I'm just starting out and I love your work. Is there any way we could speak or I can shadow you?' I get those inquiries all the time and I reach back if I can help, absolutely. I think a lot of designers would.

Really, stay on the pulse of fashion and see the movies. A lot of times when I interview people, I'm like, 'who are your favorite designers?' [and they can't answer]. Are you in, or are you not? If you don't know the actors, maybe you're not that interested. You have to know what’s happening. You have to read magazines. You have to really be passionate about it.

I've never lost the passion. That's why I still do what I do. My work is an expression of that. My work is joyous; my work is fun. I'm very lucky to get the projects that I have. I think I get them because that's what I can bring to the project: that exuberance. One of Adam Sandler's producers gave me the best compliment I ever had. He said my work can open movies and that's a pretty great compliment.

This interview has been edited and condensed for clarity.

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