30 years on, 'Clueless' is still defining fashion trends – here's how

The Star

17-07-2025

Power plaids, matching sets, athleisure – all fashion mainstays now, but in the summer of 1995, they weren't exactly on trend when the murky flannels and shredded denim of grunge ruled.
Until a fizzy comedy starring an 18-year-old Alicia Silverstone set at a Beverly Hills, California, high school rolled into theatres like a white Jeep Wrangler with a monster sound system.
No, you're not totally buggin', friends, it's the 30th anniversary of Clueless .
Directed by Amy Heckerling, who loosely based her screenplay on Jane Austen's Emma , the teen classic centres on Cher (Silverstone) and her well-intentioned matchmaking in the halls and malls of Beverly Hills.
Cher's circle of friends includes her bestie Dionne (Stacey Dash); her frenemy Amber (Elisa Donovan); Christian (Justin Walker), her crush; and Tai (Brittany Murphy), her protegee. But from the opening scene, the film's fashion vibrates with main character energy – and that's exactly what Heckerling and costume designer Mona May intended.
'We had to create these girls that are authentic but have a certain kind of fashion sense that wasn't out there' at the time, said May, who drew on her childhood in India, a European sensibility and an encyclopedic knowledge of runway shows to create the film's bold styles.
'Cher's looks were completely over-the-top in the best way,' Silverstone wrote in an email. 'But that's what made her iconic!'
Of Cher's impact, Silverstone added: 'She gave people permission to look like they cared about their fashion.'
The costume designer had a clear vision, Silverstone recalled, adding, 'Looking back it's funny because they were the adults but were much more tapped into youth culture and fashion than I was.'
Plaids featured prominently in the film. Photo: Collection ChristopheL via AFP Silverstone's close friend, designer Christian Siriano, featured several Clueless -inspired looks in his Autumn/Winter 2023 collection.
'Growing up, there wasn't a lot of film fashion that a young designer could fall in love with, and Clueless was that,' he said.
'Everybody wanted to dress like Cher.'
On a video call from her home in Los Angeles, May, dressed in a bright pink top, hat and necklace, broke down the film's most influential looks. Here are excerpts from her comments.
Cher's back-to-school ensemble
The look: The starting point was the Catholic schoolgirl uniform. How would Cher interpret it? It's the schoolgirl uniform on steroids. I looked for suits. I got a blue one that looks great on blondes, and then out of the corner of my eye I see on the rack in Neimans or Saks, the yellow (Jean Paul Gaultier) suit. And I grab it.
Alicia walks into the fitting in her sweatpants, with her dogs. She tries the blue. It's beautiful, but it's nothing. It's just pretty.
So Alicia puts the yellow on, and this is the moment that's magic. She became the queen bee. She became the ray of sunshine. We knew immediately.
The lasting influence: Plaid is timeless. I love Vivienne Westwood – it's not grunge; it's kind of punk.
The yellow was so impactful. Dior just did it two years ago. Kim Kardashian wore a yellow plaid outfit with her daughter North. That was incredible.
Read more: Michelle Yeoh and other stars light up Demna's final Balenciaga runway show
Cher's first-date dress
The look: The script says she's wearing something very inappropriate. That's all Amy wrote. It's my task as a costume designer to figure out what that is.
We found this Calvin Klein dress. It was perfect in so many ways because it looked like a slip. It was off-white, so a little bit bridal. She's a virgin sacrifice (laughs).
We probably tried 50 dresses. But again, it came together at the fitting. This is pre-Spanx. We want to make sure Alicia's feeling comfortable because she has to exude confidence in that scene. It's the perfect body-hugging dress without being skintight. The material is more cotton.
The lasting influence: It's a perfect shape for every kind of occasion. You can wear it with Birkenstocks to the beach, or dress it up with diamonds and red lipstick. That's why it will never go out of style.
Cher's layered look
The look: It's a pivotal emotional moment for Cher, because she's always so sure of herself. But she didn't pass her (driving) exam, and she finally realises she loves Josh (Paul Rudd).
The blouse is a matte silk chiffon with ruffles, and I put her 'very capable' vest over it to make sure she looks proper for the test. We did the argyle silver skirt and Mary Janes, as always.
The colour was very muted because it was where she was: Nowheresville.
The lasting influence: The white shirt is timeless. Now girls are wearing the big, oversized shirts. I think we should all have one in the closet.
Cher's gym attire
The look: Amy said we got to do black and white. We were on Melrose (Avenue), shopping at the rave shops, trying to find all the different categories, starting with Cher.
There was nothing like this in the stores. No crazy cool yoga clothes or designers like Balenciaga making spandex. I think I may be the one who started the T-shirt (under) the spaghetti strap tank trend.
I had eight weeks to prep. So we found a bunch of black-and-white stuff, whatever we could get our hands on. Amber has a 1920s swimsuit or wrestler's outfit. And Dionne is in a tuxedo shirt with white little ruffles.
The lasting influence: I created the water bottle (carriers in the film). I want to claim that Karl Lagerfeld in his next collection (for Chanel) did that. His runway shows inspired Clueless , too.
Dionne's photo-shoot outfit
The look: The burgundy dress with the white cuffs and collar was Stacey's favourite.
It is a stretch velvet two-piece, actually, a skirt and a top. The white cuffs and collar with the white knee-highs and headband – don't you think of 1960s Brigitte Bardot? France is always on my mind because they are truly the most chic people in the world.
The lasting influence: Stacey Dash was a little older than everybody else. She lived in New York City. She was super punk rock, self-assured. And she understood these clothes.
Stacey said she gets stopped to this day by women telling her how (Dionne's fashion) changed their lives. We didn't set out to do it. It was never a conversation at the fitting. We were just creating these amazing characters.
There's something about matching, too; something that is simple is really beautiful.
Amber's take on knits
The look: Pippi Longstocking was my favourite film (character) growing up. She was the coolest, most self-sufficient girl. I wanted to pay homage to her.
This look was very Missoni-inspired. We actually had to buy the fabrics and match different stripes. Amber was savvy about fashion; she just took it to another level.
The lasting influence: If you look at that outfit or her sailor outfit or the army outfit, you could wear it, especially now that everything is so quirky.
Now we wear everything with jeans. It was very fresh, mixing high and low.
The film also helped set trends in menswear. Photo: Collection ChristopheL via AFP
Christian and Cher's mall garb
The look: When we meet (Christian) we cannot know that he's gay. We have to hide his identity.
So how do we do this? When I saw a picture of Justin Walker, I was mesmerised. I thought immediately: James Dean. Rat Pack 40s, 50s and a little bit of rockabilly.
We dressed him in period pants with pleats, gabardine jackets, gabardine shirts.
In the end, he becomes the best friend of Cher. Only a fashionista with very sophisticated taste can go shopping at the mall with her.
The lasting influence: I think men will always look good in those clothes. You can go preppy with it – khaki pants with a white T-shirt – or a very nice polo and a good leather jacket.
The sage green minidress was Alicia's favourite. Because it's so comfortable. It comes back to Emma , what women wore during the Regency period – empire waist, the little puffy sleeves, the lower necklines.
I don't know anybody who looks bad in that at any age.
Read more: Dressing for two? These stars have proven that maternity style can still be chic
Tai's school dance outfit
The look: They are not mean girls. They're there for each other, even if it's making Tai over.
Brittany Murphy was so wonderful. She was an incredible actress at 17. She came on the set with her mom, and she knew immediately how she wanted to approach the character, with this kind of sadness and vulnerability.
She said, 'Mona, I really want to be as grungy as I can. I don't want to look pretty.'
She becomes this mini Cher. But it's the mall version. It's not tailored so perfectly. Maybe the colour palette is a little bit off.
And then she's trying to find herself at the party with the overalls. This is something Brittany was so brilliant at. You really see that arc, and the clothing supporting her all the way to the end, where she's this California girl, sporty and feminine.
The lasting influence: She's learned, from the pieces, who she was. And I think it's that emotion that has staying power. – ©2025 The New York Times Company
This article originally appeared in The New York Times.