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When Desperately Seeking Susan Introduced Madonna’s Style to the Masses

  • Apr 15, 2025
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This month marks the 40th anniversary of the 1985 cult film Desperately Seeking Susan, which featured a then-almost-unknown Madonna on the big screen acting like we thought she might in real life at the time – and dressing like she did.

The movie centers on a housewife with too much time on her hands, Roberta Glass, played by Rosanna Arquette, and her fascination with the free-spirited, impulsive Susan Thomas (Madonna). The two mix it up in the New York City streets of the mid-80s in what starts as a stalker (ish) turned short-term amnesia, turned self-discovery tale. 

While New York played a prominent part in the film, Madonna’s cool as hell perfectly captured the vibes of the ’80s while introducing the now megastar to a new audience with a single jacket.

Costume designer Santo Loquasto was responsible for the film’s acclaimed fashion. The costumer got his inspiration from the singer’s personal wardrobe and even dug through his own mother’s closet for pieces, including the black bustier Madonna wore. “(Madonna) put it on and looked at her bust and said, ‘your mother is some lady’, in her best Mae West delivery!” Loquasto recalled to CNN recently. “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.”

The fan-favorite 1950s jacket with an embroidered golden pyramid on the back, worn by Madonna’s Susan character on multiple occasions, played a pivotal part in the film. “In a way the pyramid jacket is used as a symbol of transformation,” director Susan Seidelman told CNN. “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.”

Our fave look? This one right here – the lace top, hair bow, layered bangles, and those rhinestone booties, c’mon.

photo: andy schwartz / corbis
photo: orion pictures / everett collection
photo: andy schwartz / corbis
photo: corbis
photo: getty images
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Wearing Staff

The Wearing editorial team curates stories that celebrate the beauty of vintage style, sustainable fashion, and eco-conscious beauty.

Related Topics
  • 1980s
  • costume design
  • fashion
  • madonna
  • movies
  • style
  • vintage
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