The Who What Wear Podcast

Episode: Clueless Costume Designer Mona May on 30 Years of Fashion Influence and Letting Girls Be Girls
Date: November 26, 2025
Host: Tara Gonzalez, Editor at Who What Wear
Guest: Mona May, Costume Designer, Author of The Fashion of Clueless

Episode Overview

In this engaging episode, Senior Fashion and Social Editor Tara Gonzalez sits down with acclaimed costume designer Mona May to reflect on the enduring legacy of Clueless—thirty years after its release. The episode explores Mona’s creative process, her favorite costume moments, and the story behind her just-released book The Fashion of Clueless. May shares personal anecdotes about her multicultural upbringing, her route to costume design, and the collaborative, innovative spirit that brought over 100 vibrant looks to the big screen despite a tight budget. The conversation is a deep dive into the art of fashion storytelling, the influence of Clueless on pop culture and style, and the power of letting femininity shine on screen.

Key Discussion Points & Insights

Mona May's Path to Costume Design (02:42–04:36)

• Mona grew up in India, Poland, and Germany, absorbing diverse, colorful cultural influences that sparked her early love for drawing and fashion.
• Initially wanted to be a fashion designer, pursued studies in Paris, Milan, London, before moving to New York and then LA.
• Discovered costume design while helping friends at USC film school—was immediately captivated by the collaborative nature and character-driven creativity.
• Quote:

  “It was so interesting to me to actually create characters, personas, to dive into people’s psychology, who they are. It was so much more than fashion.” — Mona May (03:41)

The Birth of Clueless Fashion (04:52–07:11)

• Meeting Amy Heckerling was a pivotal moment (“creative soulmate”).
• The challenge: Create a look for “rich Beverly Hills girls” no one else was wearing—pre-legally blonde, pre-girly movies.
• Went to high schools to research but found the reality (grunge era) uninspiring.
• Took inspiration from European runways rather than the current American teen scene.

Inspirations and Constraints (07:26–09:06)

• Key influences: Chanel by Karl Lagerfeld (“biker girls in Chanel”), Vivienne Westwood’s rule-breaking style, the absence of high-low mixing at the time.
• Film studios were reluctant:

  “They basically said, 'Oh, movie about girls, forget it. Put some boys in it. We'll do it.'” — Mona May (08:02)

• Low budget ($25 million), but Paramount’s hands-off approach resulted in creative freedom.
• Cast was perfectly chosen, iconic performances.

Expressing Character Through Clothes (10:12–13:41)

• Detailed breakdown of main characters’ signature styles:
  • Cher: “The number one in school,” preppy, tailored, feminine, not overtly sexy.
  • Dion: Older, New Yorker, bold colors, vinyl, leopard prints, and vintage/thrift finds mixed with designer.
  • Tai: Arc depicted through transformation—requested by Brittany Murphy to start as an “ugly duckling.”
• Fittings were key: Experimentation and openness led to iconic wardrobe choices, like Cher’s yellow plaid Jean Paul Gaultier suit.
• Quote:

  “It really is like a laboratory. This is one of my favorite parts of my job, really—in the fitting. This is when you find out what really is going to work.” — Mona May (11:27)

Iconic Looks and Happy Accidents (13:41–17:53)

• Cher’s yellow suit almost didn’t happen—tried a blue plaid first, yellow worked “like the queen bee.”
• The Alaïa dress:
  • Sourced by reaching out directly to the designer, who lent it for the film.
  • Famous “You don’t understand. This is an Alaïa!” scene is now a cultural touchstone and viral TikTok sound.
  • Quote:

    “We introduced Alaïa to the world in America. ... I was so scared when she had to get on the ground in that dress.” — Mona May (15:15)

• The power of creative flexibility: Being open to unexpected choices and how magic happens when trusting the process.

Hats, Accessories, and the “High-Low” Revolution (17:53–20:42)

• Mona loves hats, brought her European sensibility (“a signature”) to the styling—Chanel-inspired hats for Dion by KOKIN.
• Mixing high fashion and thrift/vintage was unconventional at the time—Dion embodied this:

  “I was able to kind of really shop thrift stores and rave stores on Melrose Avenue ... and then go a little bit designer and really mix it up.” — Mona May (12:51)

• The Clueless mix-and-match approach anticipated the current trend of blending vintage and high fashion.

Fashion Influence and Timeless Style (20:42–22:54)

• Clueless’s aesthetic continues to influence how young people dress; styles like layered gym tees and key accessories have become wardrobe staples.
• Timelessness is central to Mona May’s vision—references to Sophia Loren, Audrey Hepburn, iconic “forever” pieces such as the peacoat, beret, or little black dress.

Favorite Lesser-Known Looks (22:54–24:10)

• Cher’s green empire-waist dress (her own and Alicia Silverstone’s favorite), a Jane Austen/E. Emma homage—“any girl could feel amazing.”
• The “twin set” moment—Cher’s leather skirt and cream cardigan, showing her softer side (“so girly, so much heart”).

The Dream Closet & Modern Legacy (24:10–24:50)

• Clueless’s revolving wardrobe inspired real-life tech; Mona references the “Fitted” app as a modern attempt to recreate Cher’s virtual closet.

Sourcing on a Budget: The Power of Tailoring (24:57–26:53)

• Major designer moments: Dolce & Gabbana for Dion, but mostly thrift, mall shops, or Contempo Casual.
• Mona tailored every garment for a couture feel, regardless of original price.
• Key fashion tip:

  “No matter what piece that I bought, even if it was 99 cent, it was tailored perfectly because then it looks couture. ... Maybe I need to roll up the sleeve, ... crop it, ... just hem it ... you can rework your things ... That’s the personal power we want to have in life.” — Mona May (25:32)

Behind the Scenes: Collaboration and Detail (27:02–29:12)

• Creative process often last-minute and collaborative, given constraints of time and small crew.
• Importance of costume details, shoes (always age-appropriate, comfortable, e.g., Charles David Mary Janes and T-strap heels), and clever repetition due to budget limits.

The Book: The Fashion of Clueless (31:56–35:19)

• A project 30 years in the making; gives fans a tangible, intimate look at the creation of the film’s fashions.
• Features interviews with cast members, style guides, behind-the-scenes Polaroids from the Paramount vault, and Mona’s original sketchbook.
• Aims to provide inspiration, serve as a collectible, and further cement the legacy of the film.
• Quote:

  “I think it’s really cool to dive into this world in a very personal way, that now you even have a more intimate connection with the character and their fashions and the details. … This book is like joie de vivre and how we did it and talking to the actors.” — Mona May (32:26)

Notable Quotes & Memorable Moments

• On Clueless’s impact:

  “We were really breaking the ground for those [girly] movies.” — Mona May (07:11)

• On high-low fashion:

  “People didn’t wear that. ... Now it’s in everybody’s wardrobe.” — Mona May (20:59)

• On the collaborative process:

  “It was such a pivotal moment in our lives that we are so connected to this day.” — Mona May (17:17)

• On tailoring as fashion’s hidden secret:

  “Taking the clothes that you have and giving them a little bit new life … that’s the personal power we want to have.” — Mona May (26:35)

• On the longevity of Clueless style:

  “Anywhere where you open the book, I think you’ll be, like, transported to that world.” — Mona May (33:17)

• The ever-iconic yellow suit:

  “...When Alicia put that suit [on], we all had goosebumps. It was like, this is right. This is the queen bee. This is the ray of sunshine.” — Mona May (12:09)

Timestamps for Key Segments

• 02:42 – Mona’s upbringing and fashion journey
• 04:52 – Meeting Amy Heckerling and the start of Clueless
• 07:33 – Runway and designer inspirations (Chanel, Vivienne Westwood)
• 10:29 – Defining characters’ unique personal styles
• 13:41 – How the yellow plaid suit became iconic
• 14:40 – The Alaia dress story and introduction to America
• 17:53 – The power of hats and accessories
• 20:42 – Clueless’s high-low, vintage/designer mix and lasting impact
• 22:54 – Mona’s and Alicia's favorite lesser-known looks
• 24:10 – Clueless closet and its app version
• 25:15 – Budgeting, sourcing, and the importance of tailoring
• 31:56 – The creation and content of The Fashion of Clueless book

Closing Thoughts

This episode is a masterclass in costume design—offering rare insights into the creativity, passion, and teamwork behind Clueless’s legacy. Mona May’s approach to fashion is a celebration of individuality, femininity, and fun, while her advice on tailoring and timelessness is compelling for style lovers everywhere. The conversation is peppered with stories, style hacks, and memories that bring the film’s iconic fashion moments vividly to life—even three decades on.