This groundbreaking nineties model – who famously romanced Madonna and Angelina Jolie – stepped out in West Hollywood, CA on Sunday.
The 58-year-old Asian-American trailblazer was joined by her wife – MVH Strategic Partners CEO Michelle Harper – ahead of their 11th wedding anniversary on August 30.
She showcased her tattooed sleeves in a simple white T-shirt, which she paired with black knee-high shorts, and Converse-style sneakers.
The androgynous beauty was originally scouted outside an LA nightclub to model in Calvin Klein’s CK One unisex perfume campaign in 1994.
She went on to model for designers Prada, Banana Republic, Versace, Jean Paul Gaultier, Yohji Yamamoto, Donna Karan, Anna Sui, Thierry Mugler, Levi’s, J. Crew, The Gap, L.A. Eyeworks, and the United Colors of Benetton.
Can you guess who?
This groundbreaking nineties model – who famously romanced Madonna and Angelina Jolie – stepped out in West Hollywood, CA on Sunday
It’s Jenny Shimizu, whose sexual allure attracted some of the most beautiful and powerful women in showbiz, including her Foxfire leading lady Angelina.
The 50-year-old Oscar winner admitted she would ‘probably have married Jenny’ had she not married her Hackers leading man Jonny Lee Miller in 1996.
‘I fell in love with her the first second I saw her,’ Jolie confessed to Girlfriends in 1997.
‘Actually, I saw when she was being cast in Foxfire, and I thought she had just read for my part. I thought I was going to lose the job. I said to myself, “Oh, my God, that’s [the character Margaret “Legs” Sadovsky].” She’s great. We had a lot of fun.’
The Maria producer-star and the 2025 Pirelli Calendar stunner even shared a nude scene in Annette Haywood-Carter’s 1996 big-screen adaptation of Joyce Carol Oates’ 1993 coming-of-age teen novel, which only grossed $269K at the box office.
‘[Jonny] came to the set of Foxfire. He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also,’ Angelina noted.
‘If anything, he took it very seriously. When I realized that somebody like Jenny could be a deep love for me, he realized it, and he took it very seriously. If anything, he didn’t treat it just like some sexy thing.’
Two years later, Jolie reflected to Rolling Stone: ‘I realized that I was looking at her in a way that I had looked at men. And it was great, and it was a discovery. It had never crossed my mind that I was going to one day experiment with or kiss a woman; it was never something I was looking for. I just happened to fall for a girl.’
The 58-year-old Asian-American trailblazer was joined by her wife – MVH Strategic Partners CEO Michelle Harper – ahead of their 11th wedding anniversary on August 30
She showcased her tattooed sleeves in a simple white T-shirt, which she paired with black knee-high shorts, and Converse-style sneakers
The androgynous beauty was originally scouted outside an LA nightclub to model in Calvin Klein’s CK One unisex perfume campaign in 1994
She went on to model for designers Prada, Banana Republic, Versace, Jean Paul Gaultier, Yohji Yamamoto, Donna Karan, Anna Sui, Thierry Mugler, Levi’s, J. Crew, The Gap, L.A. Eyeworks, and the United Colors of Benetton
It’s Jenny Shimizu, whose sexual allure attracted some of the most beautiful and powerful women in showbiz, including her Foxfire leading lady Angelina
Jenny had previously dated the 66-year-old Queen of Pop, who cast her as ‘Production Assistant Girl’ in her 1993 music video for Rain, which was directed by Mark Romanek.
‘I mean you are not going to say no to Madonna in the nineties,’ Shimizu dished to Hulu/Disney+ docuseries In Vogue: The 90s last September.
‘Not only was it great feeling like a high-class hooker, because it was, I would get a phone call saying, “Can you meet me at my show in Paris, you’re in Europe, right?” and I would be like, “Yeah, I’m just finishing Prada, I’ll catch a plane over.”
‘And I would go to the Ritz at four in the morning and have sex [with Madonna] and fly back to Milan.’
The Chic Management-repped model added: ‘My wife is going to kill me, but that time was so crazy and fun and there was something heartfelt about certain moments.’
Last March, Ione Skye revealed she had an extramarital affair with Jenny, which involved strap-ons and safe words, but it ended in 1999 when she started feeling ‘needy and devoted.’
‘[She was a] masterful lover, sometimes a dominant one. She didn’t use whips or handcuff me to the bed, she just held this vibe,’ the 54-year-old Anaconda actress wrote in her memoir Say Anything.
The 50-year-old Oscar winner (R, pictured in 1995) admitted she would ‘probably have married Jenny’ had she not married her Hackers leading man Jonny Lee Miller (L) in 1996
Jolie confessed to Girlfriends in 1997: ‘I fell in love with her the first second I saw her…She’s great. We had a lot of fun’
The Maria producer-star (L) and the 2025 Pirelli Calendar stunner (R) even shared a nude scene in Annette Haywood-Carter’s 1996 big-screen adaptation of Joyce Carol Oates’ 1993 coming-of-age teen novel, which only grossed $269K at the box office
Jenny had previously dated the 66-year-old Queen of Pop (L, pictured in 1992), who cast her as ‘Production Assistant Girl’ in her 1993 music video for Rain, which was directed by Mark Romanek
![Last September, Shimizu dished to Hulu/Disney+ docuseries In Vogue: The 90s: 'Not only was it great feeling like a high-class hooker, because it was, I would get a phone call saying, "Can you meet me at my show in Paris, you're in Europe, right?" and I would be like, "Yeah, I'm just finishing Prada, I'll catch a plane over." 'And I would go to the Ritz at four in the morning and have sex [with Madonna] and fly back to Milan' (pictured in 1993)](https://i.dailymail.co.uk/1s/2025/08/05/01/100920805-14970629-image-m-55_1754352452349.jpg "Guess Which Female Ex of Angelina Jolie and Madonna Was Spotted in West Hollywood? 13")
Last September, Shimizu dished to Hulu/Disney+ docuseries In Vogue: The 90s: ‘Not only was it great feeling like a high-class hooker, because it was, I would get a phone call saying, “Can you meet me at my show in Paris, you’re in Europe, right?” and I would be like, “Yeah, I’m just finishing Prada, I’ll catch a plane over.” ‘And I would go to the Ritz at four in the morning and have sex [with Madonna] and fly back to Milan’ (pictured in 1993)
Last March, Ione Skye (R, pictured in 1999) revealed she had an extramarital affair with the Chic Management-repped model, which involved strap-ons and safe words, but it ended in 1999 when she started feeling ‘needy and devoted’
![The 54-year-old Anaconda actress wrote in her memoir Say Anything: '[She was a] masterful lover, sometimes a dominant one. She didn't use whips or handcuff me to the bed, she just held this vibe' (pictured April 5)](https://i.dailymail.co.uk/1s/2025/08/05/01/100922661-14970629-image-a-56_1754352510243.jpg "Guess Which Female Ex of Angelina Jolie and Madonna Was Spotted in West Hollywood? 15")
The 54-year-old Anaconda actress wrote in her memoir Say Anything: ‘[She was a] masterful lover, sometimes a dominant one. She didn’t use whips or handcuff me to the bed, she just held this vibe’ (pictured April 5)
One year later, Ione divorced her husband – Beastie Boy Adam ‘Ad-Rock’ Horovitz (R, pictured in 1995) – due to her ‘serial cheating’ after eight on/off years of marriage
‘[But] Jenny didn’t want me to be her dog. She left shortly thereafter for a modeling job and never came back to me, except as a good friend.’
One year later, Ione divorced her husband – Beastie Boy Adam ‘Ad-Rock’ Horovitz – due to her ‘serial cheating’ after eight on/off years of marriage.
Shimizu also spent quality time with Rebecca Loos – the former assistant of David Beckham, who told all about their four-month extramarital affair to the News of the World in 2004.
In 2005, the Cali native and the Dutch 48-year-old took part in a staged wedding ceremony to protest the States’ laws on same-sex marriage, which aired as Power Lesbian UK on Logo TV.
