Every so often, a cultural moment perfectly blends talent, story, and style to create something that resonates for decades. One of those moments came in 1985 with the release of Desperately Seeking Susan, a comedy-drama featuring Madonna and Rosanna Arquette. Arquette plays Roberta, a restless housewife, while Madonna portrays Susan, a mysterious downtown punk whose life is revealed through cryptic personal ads.
At the time of filming in 1984, Madonna was still rising in the music world, with only a few hits like “Holiday” and “Borderline” under her belt. Studio execs were initially skeptical about casting her, according to director Susan Seidelman, who shared the story during a Zoom call with CNN.
However, a strange twist of fate occurred during production: Madonna’s second album, Like a Virgin, was released just as filming was wrapping up, propelling her to superstardom. As her popularity exploded, Desperately Seeking Susan became “the Madonna movie,” and studio executives rushed to release it, hoping to capitalize on her sudden success—though they had no idea her influence would only grow over the next four decades.
Madonna’s rise was intertwined with her distinctive style—headscarves, oversized jewelry, and her infamous “underwear as outerwear” look—which became iconic through her portrayal of Susan. While the 1980s fashion scene can often feel dated or costume-like, Susan’s outfits maintain a timeless, effortless cool that would still fit in today’s fashion world. Even after 40 years, the film’s aesthetic continues to feel surprisingly modern.
Santo Loquasto, the film’s costume and production designer, drew inspiration from a range of sources, including his own mother’s wardrobe for Susan’s black bustier, which was actually made up of a corset and a longline bra. Loquasto reminisced about Madonna’s reaction to the piece, recalling how she quipped, “Your mother is some lady,” in her best Mae West impression. It’s hard not to see a connection between the bustier and the famous Jean Paul Gaultier cone bra Madonna would later wear during her Blonde Ambition tour in the ’90s.
Loquasto noted that his approach to designing Susan’s look was shaped by Madonna’s unique sense of style, creating an “organic” and “harmonious” fusion that he then enhanced with his own touches. “I knew I was going to exploit your sensibility because we’re all fascinated by it, and you’re comfortable with it,” he told Madonna.
He would often dump a bag of jewelry onto her trailer couch, telling her to have fun with it. Madonna loved mixing chunky beads, crucifixes, and rubber bangles, which soon became synonymous with her style.
One particular piece of clothing wasn’t inspired by Madonna’s personal preferences but was directly written into the script: a vintage 1950s olive-green tuxedo jacket. This jacket, which featured a golden pyramid embroidered on the back, became one of Susan’s most defining items and even played a key role in the plot. While Madonna herself wasn’t particularly fond of it, according to Seidelman, the jacket became symbolic, playing a pivotal part in Roberta’s transformation.
In the film, Susan trades the jacket at a second-hand shop for a pair of rhinestone boots. Roberta, fascinated by Susan, buys the jacket and, after a bump on the head, is mistaken for Susan—leading her to assume Susan’s identity and break free from her mundane suburban life. The jacket, once a symbol of Susan’s punk style, becomes Roberta’s gateway to reinvention.
In an ironic twist, when Roberta returns home, her husband Gary mocks her for buying “a used jacket.” Today, however, secondhand and vintage shopping are not only popular but often seen as environmentally conscious alternatives, especially among younger generations who cherish unique, one-of-a-kind pieces.
While Susan’s style took center stage, Roberta’s fashion evolution also told an important story. When we first meet Roberta, she’s dressed in a frumpy pink muu-muu, a far cry from the bold, edgy looks of Susan. After obtaining the pyramid jacket, she attempts to mimic Susan’s look, often clashing it with garish pinks and purples. Her fashion journey parallels her personal growth, highlighting the process of reinvention.
Seidelman noted that some of Roberta’s girlish innocence appeared to influence Madonna as well. For instance, the white lace thigh-high stockings and garter belt worn by Susan in the film bear a striking resemblance to the outfits Madonna later wore in the Like a Virgin music video, shot around the same time.
“The pyramid jacket symbolizes transformation,” Seidelman explained. “It wasn’t about Roberta becoming Susan; it was about her becoming a stronger version of herself.” This theme of reinvention echoes through both Roberta’s character arc and Madonna’s broader career, which has been marked by constant evolution.
Ultimately, Desperately Seeking Susan encapsulates the power of reinvention, a concept that resonates with Madonna herself. The movie not only solidified her style but also set the stage for her ongoing influence on pop culture. Even as Madonna’s fashion choices have evolved over the years, her 1980s look remains one of her most iconic—and much of that can be traced back to her unforgettable role in Desperately Seeking Susan.
