Dressed: The History of Fashion · Dressed Media

Clueless at Twenty-Five, an Interview with Costume Designer Mona May (Dressed Classic)

November 21, 2025·43 min·4 clips

Mona May describes the exact moment Alicia Silverstone put on the yellow suit, and everyone knew it was perfect.

This episode features fashion historians April Callahan and Cassidy Zachary interviewing renowned costume designer Mona May, celebrating the 25th anniversary of the iconic film *Clueless*. May's career spans over three decades and includes films like *Romy and Michelle's High School Reunion*, *Never Been Kissed*, and *Enchanted*. She explains that her role involves deep psychological profiling of characters to determine their wardrobe, translating vague script descriptions into fully realized visual identities. The conversation centers on how May and director Amy Heckerling created *Clueless*'s distinct, fashion-forward world in direct opposition to the prevailing grunge aesthetic of the mid-1990s. May sourced inspiration directly from European runways, mixing high-fashion pieces with mall finds and thrift store items to invent a fresh, youthful look. She details the immense workload, including creating 60 costume changes for Cher and dressing every background extra, all on an eight-week prep schedule and a $25 million budget. A pivotal moment was the fitting where Alicia Silverstone tried on the now-iconic yellow plaid suit, which immediately felt like "a ray of sunshine" and defined the character. May reveals she intentionally incorporated Empire-waist dresses as a subtle homage to Jane Austen's *Emma*, the novel on which *Clueless* is based. She also discusses her later work on *Romy and Michelle*, where she designed and constructed many of the characters' more outrageous, handmade outfits to reflect their creative personalities. An interesting insight is that Karl Lagerfeld was inspired by the gold chain cell phone holder Cher wears in the film. May emphasizes that a costume designer's signature is often in the couture-level fit of every garment, whether it's from Dolce & Gabbana or a 99-cent store. She believes the film's lasting emotional connection stems from this authenticity, making the characters feel real despite their extravagant wardrobes. The tone is conversational, enthusiastic, and deeply reverent, with the hosts openly fangirling over their guest. Listeners who love behind-the-scenes stories of filmmaking, fashion history, or 1990s pop culture will adore this episode. Those seeking a critical analysis of fashion's socio-economic impact or a structured historical narrative might find it too nostalgic and anecdotal.

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