Iconic queer ’90s model Jenny Shimizu, best known for breaking barriers as the first Asian model to walk for Prada in 1993, has recently reflected on her high-profile relationships in the new documentary, In Vogue: The 90s. Shimizu, who became a fashion icon while modelling for Calvin Klein, gained further notoriety due to her relationships with some of the world’s most famous women, including Madonna and Angelina Jolie.

In the documentary, Shimizu opens up about her romance with Madonna, describing it as “crazy and fun”. She recounts how their relationship was often spontaneous and fast-paced, sharing how the pop star would sometimes call her unexpectedly to meet in far-flung locations.

“You’d get a phone call like, ‘Hey, can you meet me at my Paris show? You’re in Europe, right?’ So I’d be like, ‘Yeah, I’m just finishing Prada. Right after Prada, I’ll catch a plane over,’” she explained. “And I would. I’d go over to her hotel, to the Ritz, at, like, 4 in the morning, have sex, and then fly back to Milan.”

iconic Jenny Shimizu who dated it girls Madonna and Angelina like wow. The rizz https://t.co/S4wwPuWhsW pic.twitter.com/FZnnaIxKUU

— hanoy⛔ (@moderngarbo) September 24, 2024

During her time with Madonna, Shimizu was also in a relationship with Angelina Jolie, sparking much media attention. Jolie has often spoken candidly about her connection with Shimizu, admitting that she “fell in love” with the model from the moment they met.

“I fell in love with her the first second I saw her,” Jolie recalled in an interview. She went on to say that she “probably would have married (Shimizu) if I hadn’t married my husband.”

Jenny Shimizu’s unique look and androgynous style made her a standout in the fashion world, and she credits designers like Calvin Klein for embracing her individuality. When she was first scouted, Klein never asked her to conform —she wasn’t told to grow out her hair or hide her interest in things like cars and trucks, a passion she developed from her previous job as a mechanic.

In 2005, Shimizu participated in a staged wedding ceremony with Rebecca Loos in protest against America’s anti-gay marriage laws. The event was part of the Sky documentary Power Lesbian UK, further cementing Shimizu’s place as a trailblazer both in fashion and LGBTQ+ advocacy.