Costume designer Mona May is behind numerous iconic looks that came out of the ‘90s and beyond—the ever-influential garments of “Clueless,” the frisky frocks of “Romy and Michele’s High School Reunion,” the fun prom cosplays of “Never Been Kissed” and multiple makeovers of “The House Bunny” only scratch the surface of her career that spans nearly 70 films and TV shows.

Below, May breaks down some of her memorable films with Variety and discusses what it was like working with frequent collaborator, actress Drew Barrymore.

There is a thread that connects some of the movies you worked on, movies like “Clueless,” “Never Been Kissed,” “The Wedding Singer” and “Romy and Michele’s High School Reunion.” There is a search for identity in all of them and the clothes are an expression of that.

Not just in the ’90s. There is “Enchanted” (2007) and “The House Bunny” (2008) and “American Reunion” (2012). To me, [those are] stories [of women] learning something very feminine about feeling good in [their] skin. How the clothes fit is very important [in that regard]. And [in] comedy, it’s the balance between funny and truth. It’s almost intuitive, how I work, how I create the mood in the world. It’s so emotional. I think colors [are] emotional.

You have a long-standing creative partnership with Drew Barrymore in both movies and TV.

Drew is very much a collaborator with costume designers. She loved shopping with me; she really is hands-on. When we did “Santa Clarita Diet” so many years later, we were just laughing in the fitting so much. She was bringing me stuff or sending me pictures. It’s so wonderful to have such an open actor who really wants to be part of the process. Alicia Silverstone [in “Clueless”] was the same way. It was truly 60 changes for her to accomplish [her looks]. And Amy Adams [in “Enchanted”] where she had to wear the crazy dress. And even “The House Bunny” where the girls had so many changes during the transformation. It’s great when you can have the trust of the actor and they want to be part of your playground.

The way her character, Julia, dresses in “The Wedding Singer” is great. That movie is so decisively extreme ’80s, to the point of parody. But with her full skirts and pretty cardigans, she looks more timeless and maybe even a little ’50s.

In the ’80s and ’90s, the big thing was the little granny dresses that we all wore with Converse or Dr. Martens. That was sort of the take. Because she didn’t have a lot of money. She went to thrift stores and picked up the feminine dresses [from] ’50s and ’40s and made a little punk-rock look in a way, but also very simple, very feminine. There was no fuss about her. She was super down-to-earth. It was all about heart; she was searching for herself.

Christine Taylor’s character is the opposite of that — sexually outspoken, with the big hair and typical ’80s look.

I love playing with character [contrasts] like that. She was a fashion victim a little bit – a little bit over the top. But it’s fun, it’s a comedy and you want to bring some levity to things. And she was game, too; went with all the accessories and the headbands and hair ties and petticoat skirt. She was so much fun to work with.

Adam Sandler’s character is an ’80s man too, but in a more disarming way.

He’s like a timeless character, little bit like Josh in “Clueless.” Those guys who just wear jeans and t-shirts and button-downs. He has his uniform for his performances, his blue jacket, which he thought was so cool, we made a vintage tuxedo jacket for him. I think both of them were so charming and innocent [through] their way of presenting themselves. They didn’t have to have all the bells and whistles that some of the other characters had for sure.

In “Never Been Kissed,” did you come up with the prom scene cosplays like Rosalind and Orlando, the Barbies and “Risky Business,” or were they in the script?

I put the ideas on the table. That’s the fun part of my job, to really marry the characters and bring something fresh to the director. The Barbies were perfect, right? Especially quite funny when later in the prom they get hit [with dog food] on their perfectly fabulous outfits. I really went over-the-top with the accessories, I built everything. I love going to the mat. I’m kind of a maximalist when it comes to creating worlds. In “Clueless,” to go back a little bit, I created a world that didn’t exist. The kids would show up in the morning with their grunge clothes. I had to give them a head-to-toe. And same with the [Never Been Kissed] prom. In comedy, a little bit of levity is always something that I look for in my costumes. I want to delight people.

What went into Josie transformation in the end, with the dress she wears on the football field?

I designed that [pink] dress for her. We really were wanting to make it so soft and feminine and beautiful and all the layers she always had. Her heart was still kind of hidden and there were so many gates that had to be destroyed and opened up. She didn’t believe in herself and then she had to kind of be this crazy character. It took falling in love and finding the truth for herself. And in the end, there she was, almost naked, completely open, nothing else to hide. I think the dress that I designed was such a great expression of that; a little bit of ruffle around the neck, quite low cut for her character and almost age-appropriate. Like, “I am my age, this is who I am.” Drew has such a beautiful body, curvy and beautiful. It was kind of an A-line dress, cut on the bias. It was chiffon. I loved it. There was just the right emotional feeling for that.

Going back to “pink,” it is often dismissed as a color perhaps because it’s too sweet…

I think pink can be sophisticated and beautiful. I treat each color emotionally. Like the yellow suit in “Clueless,” it’s a bright light when you think of yellow. [We wanted Silverstone] to be the sunshine of the school. It’s the first time we meet her, so the yellow itself was so important. I think I paint with color. To me it is as important in my work as any of the garments. It’s [about] the mood that it gives the audience, the feeling. So I’m glad you talk about pink because I love pink and I think it’s underused. And like you said, perhaps it has a derogatory meaning which is so unfortunate. I wear pink myself. There’s a funny thing that my friends say; that I have a pink boa on my grave.” I don’t mind it. [Laughs]

From pink to white, one of the outfits that stands out to me in “Romy and Michele” is the suit Elaine Hendrix wears as the cool fashion editor.

[I went with something] very sophisticated for it; [a little] European and a little bit American like Ralph Lauren. It’s timeless. It can be now or 2025; that will never go out of style. And I think it was a nice contrast with the girls who are kind of in their own world, with fashion, fun and silliness. So she had to be a little serious because we wanted to make sure that she was believable. If she says their dresses are good, then everybody’s going be like, “Oh, well she said so.” Think about Anna Wintour or someone like that who has her signature. Immediately, you’d know she’s high fashion.

A through-line my work is [pieces] that [don’t] define the age of the movie. I always look for something that’s visionary and fresh. I love the Alaïa dress in [“Clueless” for example]. He was an unknown designer at the time [outside of] couture circles and we were getting his name out to the world. It’s [also] such a funny story in the film.

A couple of decades later, I still have new fans, the young generation inspired by [my work], which is phenomenal.

There seems to be a lot more mainstream interest in costume design these days.

I’m very happy about it. As costume designers, we were overlooked. People really did not understand what costume design is [or] the amount of work that goes in there; how much costuming influences everything in the film. Seeing the actor on the screen for just 10 seconds…everything is out there [through costuming]. You can tell who they are by what they are wearing. You know psychologically how they feel; depressed or happy. [And] their economic [status]. Where they shop. What I love about my craft is the magic that happens in a fitting room [with the actor] when we try the clothes on and figure out who they are. It gives me goosebumps.