Editor’s Note: Delving into the archives of pop culture history, “Remember When?” is a CNN Style series offering a nostalgic look at the celebrity outfits that defined their eras.
CNN
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Every now and then, a piece of pop culture will capture the perfect storm of talent, story and style to withstand the test of time. One such example is the 1985 comedy-drama “Desperately Seeking Susan,” starring Rosanna Arquette as bored housewife Roberta and Madonna as the titular Susan, an enigmatic downtown punk who captures Roberta’s attention through personal advertisements in a newspaper.
When Madonna was cast, ahead of filming in the summer and early fall of 1984, she was a fledgling pop star with only modest hits such as “Borderline,” “Holiday” and “Lucky Star” to her name. Studio executives had to be convinced of her role in the movie, director Susan Seidelman recalled, on a Zoom call with CNN.
But, during filming, a rare phenomenon occurred: Madonna became a superstar after the release of her second album, “Like a Virgin”, and suddenly, “Desperately Seeking Susan” became largely viewed as “the Madonna movie” instead of a second-rate feature film. Studio executives then rushed to release the movie to capitalize on the singer’s success, which they thought would be a flash-in-the-pan (little did they know that Madonna would go on to create 18 multi-platinum albums and wield cultural influence 40 years later).
Madonna became an influential figure in pop culture, in part through her style, which included headscarves, heavy costume jewelry and wearing underwear-as-outerwear — all of which became synonymous with her character in “Desperately Seeking Susan”. Despite the film’s 40th anniversary this year, it still feels modern. And while ’80s fashion can easily veer into costume-like territory, the simplicity and effortless cool of Susan’s outfits wouldn’t look out of place today.
The film’s costume and production designer Santo Loquasto pulled garments and inspiration from across several decades, including his own mother’s wardrobe for Susan’s black bustier, which was actually two pieces: a corset and a longline bra. “(Madonna) put it on and looked at her bust and said, ‘your mother is some lady’, in her best Mae West delivery!” laughed Loquasto as he spoke to CNN via Zoom. One can’t help but wonder if the seeds of the iconic Jean Paul Gaultier cone bra, which Madonna would go on to wear in the music video for her song “Vogue” and on her “Blonde Ambition” tour in the ‘90s, were planted here.
Loquasto explained that his approach to creating the looks for Susan in the film was guided by Madonna’s own approach to fashion, which made for an “organic” and “harmonious” amalgam that he simply “embellished” with his own touches.
“I’m going to exploit your sensibility totally because we’re all fascinated by it and you’re comfortable with it,” Loquasto recalled telling her.
“I would shake a baggie of jewelry onto (Madonna’s) couch in the trailer and say, ‘I’ll be back in an hour, have a ball.’ And she would go at it,” he continued — layering chunky beads, crucifixes and rubber bangles that she would later become known for.
However, there was one item of clothing that wasn’t gleaned from Madonna’s personal tastes but was included in the script written by Leora Barish — a 1950s olive green tuxedo jacket with a golden pyramid embroidered on the back, which was so often worn by Susan that it became not only one of her character’s key identifiers but also a major plot point. (Though, Madonna herself wasn’t a fan of the jacket, according to Seidelman.)
In the film, when the jacket is traded by Susan for a pair of rhinestone boots at a second-hand clothing store, it is purchased by Roberta, who in her fascination with Susan has been following her after answering one of her personal ads. But after an accident in which Roberta hits her head, she’s mistaken by an acquaintance for Susan because of the jacket, and Roberta reluctantly assumes her identity as an escape from her suburban existence.
On Roberta’s return home, her purchase is met with derision by her ineffectual husband Gary: “You bought a used jacket? What are we, poor?” he mocks. It’s a jeer that now feels laughably uninformed as vintage and secondhand shopping enjoys a surge, particularly among younger shoppers, who view it as an environmentally conscious alternative to buying new, while also being drawn to unique pieces that allow them to express their individuality.
While Susan’s style gets all the attention, there’s a story to be told in Roberta’s awkward glow-up, too. When viewers first meet Roberta, she’s wearing a shapeless pink muu-muu with a Peter Pan collar that one would imagine being worn by a toddler or grandmother. Upon securing the pyramid jacket — the only cool item of clothing Roberta has ever come into contact with, it would seem — she clashes it with garish pinks and purples despite her desperate attempt to mirror what Susan would wear.
Roberta’s sensibilities may have inadvertently left a mark on Madonna, according to Seidelman, observing that some of Roberta’s girlishness in later scenes appeared to have rubbed off on the singer. For example, the white lace thigh-high stockings and matching garter belt worn by Susan bear an uncanny resemblance to the costumes worn by Madonna in the video for “Like a Virgin,” which was shot around the same time.
“In a way the pyramid jacket is used as a symbol of transformation,” explained Seidelman. “The idea wasn’t that Roberta was becoming Madonna’s (character); it was that she was becoming a more empowered version of herself. She’s not there yet, but she’s on the way.”
Ultimately, that was the film’s message: reinvention. The same can be said of Madonna, whose personal style evolution over her boundary-pushing career has influenced many pop stars that followed. Yet, despite Madonna’s many legendary wardrobe moments, her style in the ‘80s remains one of her most iconic and instantly identifiable looks — and perhaps that’s in no small part thanks to “Desperately Seeking Susan.”