The Most Iconic Outfit in 'Clueless' Almost Didn't Happen

Even for people who didn’t grow up in the ‘90s, the films of that decade are so deeply embedded in our culture that they inform the style of today. What would a tartan skirt be without Clueless? Would Lycra minidresses be the same without Romy and Michelle’s High School Reunion? How about a hot pink cropped cardigan without Never Been Kissed? These are the outfits that not only helped develop characters but made their way into wardrobes around the world. For this and more, there is one person you can thank: costume designer Mona May.

For 30 years, the designer has been creating some of the most iconic outfits that Hollywood has ever seen – the ones that you can bet will show up at a Halloween party and win the best costume award. Ahead of the 25th anniversary of Clueless, one of her first major jobs, May talked to InStyle about how she was able to help shape a fun movie about rich teenagers and make it into a full-blown fashion phenomenon.

“I think that the most amazing thing to me is how it's stood the test of time and how many generations are really affected by it,” May said reflecting on 25 years of being asked about the film. Over the years, she’s had mothers who were teens at the time the movie came out, and their daughters who saw it just a year ago tell her how much it means to them. She attributes this in part to the fact that most of the cast and crew was new to the scene (even the star, Alicia Silverstone) making it more authentic. “I was quite young at the time. It was my first big studio picture, and the cast was really young,” she said. “Alicia Silverstone only did a music video [Aerosmith's "Cryin',"] and that's how she came to be famous. It just was a really cool experience; a lot of times people ask me, ‘Well, did you know you were making a hit?’ But really, we were just working on a cute movie that was fun.”

While lines like “That was way harsh, Tai” and “You’re a virgin who can’t drive,” are part of what gave the movie longevity, it’s the costumes that most people will never forget. Personally speaking, I not only dressed up as Cher twice in my 20s, my colleagues and I even made a whole video of recreating our favorite looks in quarantine just two months ago. I am not unique. There are dozens of articles dedicated to these outfits and how to make them out of what's in your own closet. At the end of the day, Clueless is a fashion movie. And that means it was a big job for Mona.

“Cher had 60 changes, plus 45 for Dion,” she says. “They were always together. So, it was a huge amount of clothes. At the time, [costume design] wasn’t the machine it is now, there was not getting the clothes for free from PR. There was no internet. I had to go and get Collezioni Magazines, those big thick books of photos for $80. It was a lot of money at the time but I really needed to look at what's happening on the runways in Milan and then Paris and in London to find those key pieces.”

RELATED: 12 Clueless Outfits That Are Still Relevant in 2020

The difficulty in finding hundreds of outfits for the film had consequences that could have changed some of the most important scenes in the movie. Notably, the one where Cher gets held up at gunpoint. In the scene, the attacker tells her to get on the ground. She turns to him and says, “You don’t understand, this is an Alaïa,” as she opens her jacket to reveal her dress.

“The Alaia dress was a hard thing to get,” May said when I asked her about it. “Nobody knew who Alicia Silverstone was, and the movie was not a big-budget. There was no internet to email. There were no PR people giving clothes away. So, that was a big get for the movie, because we actually had to find connections through someone to the designer, to Paris, and get the dress. I had to alter the dress when it got there which was very much a drama not to destroy this beautiful piece we got to use.”

Interestingly, even though Alicia Silverstone really embodied a character who would be more concerned about a stained designer look than, uh, her life, according to May, that was not what the young actress was like at all. “Alicia was a hippie. She was always into dog rescuing, she was wearing her sweats and she was this funky girl who was just really into nature and didn't care about clothes. It was a very interesting transformation for her. Some of the iconic looks, like the Calvin Klein dress, were hard because she was not used to it. It was not comfortable for her personally, but I think when you're trying clothes for 60 changes, you're going to learn, you're going to have to change your whole point of view about clothes and what they represent.”

Speaking of what clothes represent, there is one look that fully embodies the entire film for most fans: the yellow suit. It’s been replicated for decades by fashion brands like Guess and Urban Outfitters, and been revisited in pop culture through music videos like Iggy Azalea's “Fancy.”

“It was the opening of the movie and we had to make an incredible impact,” May recalls. “We had a blue suit, we had some other stuff that we were trying on, like skirts and sweaters because her signature was the cardigan sweaters. But it was the opening scene of the movie and it really needed to be eye-catching. So when she put it on, we were like, ‘This is it.’ It was sunshine. The yellow was really also emotionally the right color too. It wasn't red and dramatic. Blue was pretty, but it didn't have that oomph. She was the sunshine. She was the brightest thing in the school.”

May has had an entire career in the 25 years since Clueless was released, working on everything from Enchanted to most recently, Santa Clarita Diet. In those years, a lot has changed, but the pandemic has thrown a whole new curveball her way. Production has completely shut down on major film and television sets, but ultimately, she thinks, the industry will endure because movies, like Clueless, are important for culture.

May explains, “I think the art of storytelling will not change at all. At the end of the day, it’s where we get our life force.”