Hey WNVM-ers,
Fawnia here again, as Cheryl is on sabbatical for a few weeks! Last week, I celebrated the 30th (!!) anniversary of Clueless with the film’s costume designer Mona May, and she shared some fun style tips and ‘90s movie memories in an interview below.
A scheduling note: We’ll be taking the last two weeks of August off, but will be running the special monthly issue the week of August 18.
In news, Jennifer Aniston’s longtime hair stylist, Chris McMillan, spills the tea on multiple mediums, an egregious case of Gen X erasure, and I want Winona Ryder’s shaggy mullet. Enjoy the last days of summer and remember to wear sunscreen!
Per usual, you may need to read the entire newsletter in your browser. And, if you’re feeling generous and are totally buggin’ that Clueless is 30, please give us a heart at the bottom of the post.
‘Clueless’ style architect Mona May on what c-suite fashion job Cher would have in 2025 and why ‘90s style is timeless
By Fawnia
It’s hard to wrap my head around the fact that Clueless just turned 30 — the seminal ‘90s movie is now a full Timmy Chalamet or Gigi Hadid. I mean, I feel like I haven’t (spiritually) aged a day since I first watched it, Alicia Silverstone’s effervescent charm remains evergreen, and the classic feels as fresh as the day it premiered. The vibrant, playful, and still-inventive fashion, by costume designer Mona May, will never go out of style, either — from Cher’s yellow plaid school suit to the concept of a “most capable outfit.”
A trio of founders — two younger than the movie — have engineered a virtual app version of Cher’s dream closet organizer, FITTED. May collaborated with the startup for a month-long 30th birthday celebration, including a full day of styling sessions and a cocktail party at the chic Luisa Via Roma flagship in Noho.
I arrive as May attempts to wind down her packed day — styling a non-stop stream of total Bettys, of all ages, in plaid mini-skirt sets, statement hats, and feather boas. I couldn’t help but join the fun, as May quickly grabbed the perfect combo of an Alessandra Rich red tartan ruffled bustier and kilt-skirt set, crystal-trimmed Mary Janes, and a black beret for me. All the wannabe-Chers and Dionnes also clamored for May to join their photos, and the costume designer happily obliged — running in and out of the fitting room to happily pose for the camera. “Whatever!” she exclaimed, while making the Amber “W” hands sign.
“Tonight is just very emotional because all these women are coming and I’m styling them in the ‘90s Cher and Dionne-inspired looks. They have an emotional connection to the movie and tell me how old they were when they saw the movie and what they bought,” said May, as we huddle near the end of an expansive rack of Clueless-referential designer and vintage pieces.
“Mothers in their 50s are coming with their 16-year-old daughters,” she continued. “To inspire someone — to maybe give them some confidence to be fun and to explore and be powerful — there’s nothing better in life for an artist.”
Ahead, May, who also created the indelible costumes in iconic ‘90s movies — Romy and Michelle’s High School Reunion, Never Been Kissed, and The Wedding Singer — discusses what fashion job Cher would have in 2025, how to channel ‘90s style without looking like you’re wearing old clothes, and why Will Ferrell made her laugh during his Night at the Roxbury fittings.
Congratulations —you have a big year with your book, The Fashion of Clueless, coming out in October. While you went back to research, talk to the people involved — what was something that you discovered about designing the Clueless costumes that you didn’t realize at the time?
The most surprising thing is that it has lived for 30 years. When I did the movie, there was no Style.com [now Vogue Runway]. Everything was analog. Computers and cell phones were just coming into existence. I had to really go to the fashion shows and see how I could bring high fashion to Beverly Hills and change the world. Because everybody was wearing grunge [in the early-‘90s]. I was able to bring my own style, and the timelessness of it is surprising. You’re looking at the outfits and they are not outdated or stale. I mean, they are ’90s-inspired, but you want these pieces into your closet now.
So ‘90s style is going strong. As a person who wore Cher-inspired clothes when the movie was out, and loves ‘90s vintage now, how do I wear ‘90s trends without looking like I’m wearing my old clothes?
Well, I think that you can look at Clueless! Because Clueless really is the testament of wearing something that is ‘90s-inspired, but it’s not outdated. Because the clothes fit well. Because the clothes are tailored.
I was born in India. I grew up in Poland. I’m from Berlin. I lived in New York, Los Angeles, all over the world, and I brought something to this movie that’s very global and timeless. When you think of Sophia Loren, Audrey Hepburn, Twiggy and the elements of their wardrobes — those are the girls that are timeless. Think: twin sets, empire-waist dresses, cap sleeves, an A-line skirt, little peplum jackets. This is stuff that is always in your wardrobe. Stuff that you’re gonna take off the hanger and put on, and you’re gonna feel completely 100% confident. It’s female-empowering clothes.
That makes me think of Cher’s ‘most capable looking outfit’ and ‘business women’ skirt suits from Romy and Michele’s High School Reunion.
Yes, yes. A white shirt [from Fred Segal] and how do you pair it? What was really interesting about what I brought into the ‘90s with this film was the high-low dressing. That wasn’t really in then. But now we can wear designer [pieces] with jeans. We can have a Balenciaga purse with flip-flops. So this is the freshness. So always think of who you are. What do you want to represent? What’s your style? That’s what’s going to bring you confidence.
Cher famously wore Calvin Klein and Alaïa and shopped at Fred Segal. If she was a teenager today, what designers would she be wearing?
Cher is a little bit of a control freak; the outfit always has to be put together, like tailored and matching head to toe. Timeless Chanel. Maybe Christian Dior. Loewe. Prada. Maybe she’s going to The RealReal because she would be sustainable. She saves the world and she thinks about [the environment].
Her Pismo Beach disaster relief efforts!
Yes, Pismo Beach. I think that she would be a CEO of a place like The RealReal. Because she’s so smart. She was ahead of her time.
I love that. She was and still is. You also brought us iconic ‘90s movies and characters, like Drew Barrymore’s Josie Grossie in Never Been Kissed and Julia in The Wedding Singer.
I worked with [Barrymore] many times, even the TV show ‘Santa Clarita Diet.’ I love working with actresses, when they’re really starting in the business, and giving them confidence. Because as a costume designer, we’re really creating the character, but we have to [support] the actor. My job is to make her feel she’s going to be great during the fitting. Because when Alicia was coming into the fitting, she was in her flip-flops and sweats and with her two dogs. We gave her the confidence as Cher.
Drew is amazing and the same. I worked with Emma Stone in House Bunny [2008]. A lot of these women were learning about themselves, and that’s a great moment for me to be there and help them.
The 1998 movie A Night at the Roxbury is one of my favorites, and when I first just fell in love with Will Ferrell. The Butabi brothers in their big suits dancing to Haddaway’s ‘What is Love’ are so iconic, too. What was it like in fittings with Will? Because that was one of his early movie roles.
Oh my god, oh my god. I just was on the floor every day crying because of the way that [Ferrell and Chris Kattan] moved — crazy moves — and their jokes. I had to make their suits from a special stretchy fabric shiny because otherwise they were ripping them up. You know, every butt move, every arm move. Then all their sheer shirts. One of the craziest moments was when they’re wearing those little bikinis. I’m making them [in the fittings] and [Ferrell and Kattan] are wiggling [May shakes her hips around and laughs, as I wish TikTok existed back then.]
Seriously, working with comedians is so much fun. That’s why I love Romy and Michele, because Lisa Kudrow, and Anna Farris in House Bunny, take the piss out of themselves. They’re not so serious. For a costume designer to get this whimsy…and I love a lot of the humor, like Drew Barrymore in Never Been Kissed when she’s in the white feathered top [in the school cafeteria]. The costume designer can bring these things to the actors to use as wardrobe props.
[Clueless director] Amy Heckerling was amazing too, because it’s like, we picked the Alaïa and then she wrote ‘but it’s an Alaïa!’ into the script. We picked ‘Calvin Klein.’ It’s working with directors and writers as our co-creators. [Costume designers] can bring something very unusual to the table that’s so creative.
We are two Gen X journalists who celebrate people of our generation doing cool things, as well as analyze all the ’80s and ’90s nostalgia in current pop culture, fashion, and beauty. Read more stories like this one here!
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Chris McMillan, the hairdresser responsible for both “The Rachel” and Leslie Bibb’s “cunty little bob” in “The White Lotus,” is launching a long-overdue eponymous hair care brand. He’s making the rounds in the beauty press at the moment, and let me tell you, this man has stories. I highly recommend listening to his interview with Carlene Higgins and Jill Dunn on the “Breaking Beauty” podcast. Hear: ‘90s model and fashion references galore, how his experience doing Christian Slater’s hair for his True Romance press junket led him to Jennifer Aniston, and other assorted low-stakes celeb gossip. He honestly needs his own podcast. -CW [Breaking Beauty Podcast]
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Speaking of ‘90s fashion, Sofia Coppola is debuting her first documentary, Marc by Sofia, about designer Marc Jacobs, at the Venice Film Festival. They first met in 1992 backstage at the fashion show for his now-infamous Perry Ellis “grunge” collection. -CW [W Magazine]
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We have quite a few bones to pick with the revisionary history and Gen X erasure in this “Millennials Are Changing What 40 Looks Like” story. But I shall single out this Instagram caption: “Millennials may actually be the first to push beyond aging stereotypes.” Um, Jennifer Lopez? Angela Bassett? Lucy Liu? Gwyneth “Goop” Paltrow?! Us?! We co-sign this commenter: “So pretty sure Gen X already did this.” -FSH [Elle Australia Instagram]
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The Spinal Tap II: The End Continues trailer is out, and it feels especially modern in light of all the reunion/farewell/nostalgia/legacy touring that is happening, not to mention the glut of celebrity documentaries now. There are guest stars galore (Sir Paul! Elton John! Fran Drescher!). The lads asking Questlove to be their drummer is hilarious. -CW [YouTube]
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Lots of Gen X icon deaths this past week. It really makes you feel…mortal, doesn’t it? Some words of wisdom about how to mourn people who were formative in our youth. -CW [USA Today]
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This photo series of teens from the early ‘80s through the ‘90s is really moving. -CW [New Yorker Instagram]
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Winona Ryder is on the cover of Elle UK’s September issue, with an interview I wish went on for 3000 more words. She tells of being cast as “just the mom” on “Stranger Things,” how female directors told her to get Botox, the effed-up stuff that happened on ‘90s movie sets, the tale of a rotisserie chicken that Christopher Walken gave her, and how Heathers lost her an acting job. (Also, LOVE the mullet-y shag she has.) -CW [Elle UK] Would my hair do this??? -FSH, who just got a wolf cut because her “party in the back” was too short for a Charlize Theron Old Guard 2 mullet.
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Oh whew. The new The Naked Gun, out on August 1 and starring Liam Neeson and Pamela Anderson, is good. -FSH [The Hollywood Reporter]
