Dressed: The History of Fashion

Episode: “Clueless at Twenty-Five: An Interview with Costume Designer Mona May (Dressed Classic)”
Host: Dressed Media | Aired: November 21, 2025

Episode Overview

This episode of Dressed marks the 25th anniversary of the cultural touchstone film Clueless by welcoming Mona May, the film’s legendary costume designer. Hosts Cassidy Zachary and April Callahan, both fashion historians, explore with Mona May the enduring influence of Clueless on fashion, her unique journey into costume design, and her creative process. The episode offers an insider’s look at how Clueless’s now-iconic costumes were conceived, as well as Mona’s work on other seminal films, touching on the importance of authenticity, collaboration, and innovation in costume design.

Key Discussion Points & Insights

1. Mona May’s Reaction to Clueless’s Anniversary & Ongoing Popularity

• Mona shares her excitement (04:49):
  • Overwhelmed by the love and recognition during the 25th anniversary celebrations.
  • Notes that costume designers are often "behind the scenes," so this attention is particularly special.
  • On the mystery and depth of the job:

    "We really have to be the psychologist, like a detective… It’s a lot of details that goes into this that people don’t really understand. I think it’s kind of a mysterious job in a way." — Mona May [04:49]

2. The Cultural Stay of Clueless as a Fashion Film

• Cassidy reflects on the film’s generational impact (08:29):

  • Clueless was formative for her and countless others in their relationship with fashion.
  • Many listeners likely share the experience of obsessing over and emulating the film’s style.

• Mona on why the film endures (06:20):

  • Clueless brought a fresh, high-fashion approach filtered through a youthful, authentic lens—opposite the prevailing grunge trends of the era.

  • Collaboration with director Amy Heckerling was key, bringing in Mona’s European sensibility and using runways as inspiration.

    “Everything had to be invented, taken from the runways, Paris and… Milan… but then everything had to be translated into high school… they had to feel authentic.”
    — Mona May [06:20]

  • The emotional resonance with characters and their realness is what Mona believes gives the film its lasting power.

3. Mona’s Formative Years and Path to Costume Design

• Cultural and family influences (09:13):

  • Born in India to Polish and German parents, then lived in Kolkata, Poland (during communist times), Germany, Paris, Milan, and eventually LA.

  • Exposure to saturated color in India and a cosmopolitan background deeply affected her aesthetic.

  • Early love for fashion: as a child, would draw dresses, tell her mom what to wear, and reorganize closets.

    “Maybe the first things that I saw in my life were just incredible color of India… The yellow, the reds, the pinks, the blues, the jewelry…”
    — Mona May [09:13]

• Entry into costume design (12:49):

  • Came to LA, studied at Fashion Institute, began by working on student films before transitioning into major features.

4. Working with Amy Heckerling & Costume Design as 'a Character'

• Fashion as narrative centerpiece (13:42):

  • In Clueless, fashion wasn’t just set dressing—it was an essential character.

    “How do they look at life? They look at life through clothes. Everything is about the clothes.”
    — Mona May [13:42]

  • Highlighted the challenge of creating 60+ outfit changes for Cher, inventing a new “high-low” mix before it was fashionable, and dressing every extra for authenticity—all on a tight budget.

    “At the time, there was no mixture of high and low… what I also did… I mixed those. So on Dion, you have a vinyl skirt…Then you have the leopard jacket… then you have the 50s purse and then you have the knee highs.”
    — Mona May [13:42]

5. The Process: Collaboration, Invention, and Authenticity

• Cassidy asks about iconic tennis scene (19:08):

  • Everything was pre-fit, grounded in reality but elevated for the film.

  • Cher and Dion’s gym looks were individualized within the “uniform.”

  • Importance of joy and fun during the creative process with Amy Heckerling.

    “Everything was coming from that heart. Authentic heart.”
    — Mona May [20:13]

• On striking a balance between the character and spectacle (21:51):

  • The key challenge is not allowing the clothing to overshadow the character, while still being boldly stylized.

  • Fittings with actors are crucial—the “magic” happens when costume and performer meet.

  • The iconic yellow suit was selected when it “lit up the room” in the fitting with Alicia Silverstone:

    “She put that yellow suit on… and me and Emmy and everybody just looked like, ‘Oh this is it’… Like a ray of sunshine…”
    — Mona May [22:17]

6. Clueless as a Catalyst in Fashion

• Fashion forecasting and trendsetting (27:18):

  • Mona deliberately avoided trends that would quickly become dated, instead seeking timeless, classic silhouettes with a twist.

  • Drew inspiration from European runways and adapted looks to high school setting.

  • Impact of film costumes influencing real-world fashion, e.g., Karl Lagerfeld referencing the film’s designs.

    “You’re bringing something to the screen that doesn’t exist...You have to really go far… six months ahead or a year ahead to really bring something fresh…”
    — Mona May [27:18]

• On the yellow plaid suit’s lasting fame:

  • Cassidy argues it’s as iconic as Marilyn Monroe’s white dress.

7. Homage to Jane Austen’s Emma

• Intentional Regency fashion cues (34:08):

  • Subtle use of empire waists and feminine details as tribute to Emma, upon which Clueless is based.

  • Also driven by fit and universal flattery, wanting every girl to feel able to adopt the style.

    “Subtle and intentional. I wanted to definitely pay homage. I love that story. It’s so beautiful. And I think the femininity too of that time, which I could actually help to bring back…”
    — Mona May [34:08]

8. Discussing Romy and Michele’s High School Reunion

• The craft of designing for adult characters (36:44):

  • More latitude to go sexy, wild, inventive—many pieces custom made.

  • Focus on character differentiation through color, fabric, accessories.

  • Importance of team: acknowledges the unsung contributions of her staff.

    “I would be nothing if I don’t have the girls who are gonna have the same passion as I do to find those cherry earrings that they just were perfect for that scene.”
    — Mona May [38:37]

9. Continued Influence and Legacy

• Impact on new generations (41:01):

  • Mona receives frequent letters from aspiring costume designers inspired by her work.

  • Actively sharing more of her process and sketches online (Instagram, monomay.com).

    “You guys can go [to my website]. And there’s like, beautiful sketches and there is just truly tremendous amount of work to see on my website… I just will keep sharing stuff with you guys.”
    — Mona May [41:01]

Notable Quotes & Memorable Moments

• On the emotional connection and authenticity:

  "That’s why the film has lived so long, because it’s such emotional connection that people have to this film with the fashion, with the look, to kind of making you feel good." — Mona May [06:20]

• On inventing the aesthetic mix:

  “At the time it was all grunge… I was able to get some of the Alaia and the Dolce and the things. But then I had to go to the mall and figure out what’s in the mall already that I can create in this future.” — Mona May [13:42]

• On fitting clothing to character:

  “Sometimes you have to put your own taste onto the side and really concentrate who these people are on screen, who the characters are. I think it can make or break the film.” — Mona May [20:13]

• On joy in the creative process:

  “Those moments are, to me, one of the most awesome moments in the career, like being with Alicia and putting the yellow suit on after trying so many different things and going, ‘Oh this is it.'” — Mona May [22:17]

• On giving back & inspiring designers:

  “I get so many beautiful notes and letters. And please, people follow me on Instagram. I’m being much more creative on Instagram because now I got the bug. …Please direct your listeners and I just will keep sharing stuff with you guys.” — Mona May [41:01]

Key Timestamps for Major Segments

• 04:49 — Mona on the anniversary attention and hidden labor of costume designers
• 06:20 — Shifting from grunge to a high-fashion, yet authentic high school aesthetic
• 09:13 — Mona’s multicultural upbringing and journey into fashion
• 13:42 — Collaboration with Amy Heckerling & building the Clueless “world”
• 19:08 — Designing the tennis scene and pre-fitting process
• 21:51 — The balance between character & spectacle; the “magic” of actor fittings
• 24:22 — The iconic yellow suit, the computer wardrobe, and signature details
• 27:18 — Fashion as forecasting, influencer, and legacy
• 34:08 — Homage to Emma, empire waists, and universal design principles
• 36:44 — Designing and manufacturing for Romy & Michele
• 41:01 — Encouragement for future designers; resources for further exploration

Tone & Style

Throughout, the episode maintains a tone of enthusiasm, passion, and deep appreciation for fashion’s power to shape culture and identity. Mona May’s warmth and infectious excitement are matched by the hosts’ gratitude and admiration. The dialogue is accessible yet insightful, mixing behind-the-scenes technical detail with broad reflections on aesthetics, history, and creativity.

For Further Exploration

• Mona May on Instagram (@monamay) and monomay.com for sketches, process, and visual archives
• Clueless streaming on Netflix (as of the anniversary)
• Previous Dressed episodes on fashion in film, including a two-part deep dive into Clueless

Conclusion

Mona May’s vision for Clueless (and subsequent films) isn’t just about dressing characters but creating enduring, emotionally resonant, and empowering style narratives. Twenty-five years later, her work continues to inspire designers, movie lovers, and anyone who has ever asked, “What should I wear?”—affirming that costume design is as much about psychology, culture, and storytelling as it is about clothes.