Jenny Shimizu

Sexuality: Lesbian
Gender Identity: Cisgender woman
Date of Birth: June 16, 1967
Place of Birth: San Jose, California, USA
Nationality: Japanese American

Overview

Jenny Shimizu is a Japanese American model, actress, and modeling agent who shattered barriers in the fashion world as one of the first out lesbian supermodels and the first Asian model to walk for Prada. With her androgynous aesthetic, tattoos, and masculine style, she defied traditional beauty standards and became a queer icon of the 1990s. Her high-profile relationships with women like Madonna and Angelina Jolie kept her in the spotlight, while her later work as a modeling agent, designer, and mentor solidified her legacy in both fashion and LGBTQ+ history.

Early Life

Jenny Lynn Shimizu was born on June 16, 1967, in San Jose, California, and raised in Santa Maria, a city on the Central Coast of California. She is of Japanese American heritage and grew up in a working-class environment. Her upbringing was not connected to the fashion world. Instead, her early interests included cars, motorcycles, and mechanical work.

After high school, Shimizu trained and worked as a motorcycle mechanic. This career path was unusual for women at the time and reflected both her independence and her masculine-of-center identity. She embraced traditionally “masculine” interests and aesthetics long before being scouted as a model.

Shimizu has said she never felt the need to hide her sexuality or gender presentation. From a young age, she identified as lesbian, and her butch style was apparent even before her public career began. Her openness and authenticity would later become a signature strength that set her apart from others in the modeling industry.

Her transformation from a motorcycle mechanic to an internationally recognized fashion icon was unexpected. Her unique look, tattoos, and self-possession caught the attention of a photographer who scouted her, launching a path that changed the course of fashion history.

Modeling Career and Breakthrough

Jenny Shimizu’s modeling career began in the early 1990s in a way that mirrored her unconventional presence in the fashion world. While working as a motorcycle mechanic in California, she was discovered by a photographer who saw potential in her striking, androgynous look. She was soon cast in advertisements for Calvin Klein, becoming the face of the CK One fragrance and Calvin Klein Jeans campaigns. Her lean frame, short hair, tattoos, and masculine-of-center style contrasted sharply with the ultra-feminine beauty standards of the time.

Rather than asking her to change, Calvin Klein embraced her exactly as she was. Shimizu was never told to grow out her hair or tone down her personality. Her authenticity was central to her appeal and allowed her to represent a new archetype in fashion. Her appearance in the minimalist and gender-neutral CK One ads quickly made her a standout figure in the industry and cemented her place as a fashion icon.

She also modeled for Banana Republic in its “American Beauty” campaign and went on to walk for several major designers, including Jean Paul Gaultier, Anna Sui, and Donna Karan. However, one of her most historic moments came in 1993 when she walked in the Prada womenswear show for the Spring and Summer 1994 collection. She made history as the first Asian model to walk for Prada and the first model of color to open the show. Her presence on that runway marked a significant milestone in the ongoing fight for racial and queer representation in fashion.

Throughout the 1990s, Shimizu became one of the most recognizable faces in high fashion, not just because of her campaigns but because she refused to conform. Her visibility as a masculine-presenting lesbian of color was groundbreaking, particularly in an industry dominated by Eurocentric, ultra-feminine ideals.

Shimizu’s work as a model extended beyond the runway and print. She became a cultural figure and a symbol of rebellion, self-determination, and queer power. She was featured in numerous queer publications, including Out, DIVA, and Curve, and was often celebrated not just as a model but as a trailblazer.

Her impact on fashion went beyond aesthetics. She helped to redefine what was considered beautiful and marketable in mainstream media. She opened doors for other gender-nonconforming and racially diverse models, proving that fashion could be more inclusive and expansive than it had previously allowed.

Acting and Media Work

Jenny Shimizu made her acting debut in 1996 in the film Foxfire, where she starred alongside Angelina Jolie. The film, which followed a group of rebellious teenage girls confronting abuse and patriarchy, mirrored Shimizu’s own defiant and nonconforming spirit. Her portrayal of a tough and loyal friend helped solidify her presence not just in fashion but also in queer cinema. The off-screen romance that developed between Shimizu and Jolie drew major media attention and added to her visibility within both LGBTQ+ and mainstream audiences.

In 2007, Shimizu appeared in the queer feminist indie film Itty Bitty Titty Committee, directed by Jamie Babbit. The film focused on a radical feminist group and centered queer and gender nonconforming characters in ways that were still rare for the time. Shimizu played a supporting role that once again aligned with her identity and ethos, adding further credibility to her reputation as an icon of lesbian representation in media.

She also joined the cast of Dante’s Cove in its third season, a supernatural LGBTQ+ drama produced by Here TV. The show featured queer characters at the center of its storyline and cultivated a cult following. Shimizu’s appearance was seen as a major addition to the series and further expanded her presence in queer television.

In 2005, she appeared as a special guest on America’s Next Top Model, where her role was to mentor and evaluate aspiring models. Her presence brought a grounded and authentic energy to the show, especially for contestants who did not fit traditional beauty norms.

She later served as a judge on Make Me a Supermodel during its second season, broadcast by Bravo TV in 2009. Her contributions as a judge were praised for offering valuable insight from someone who had challenged industry standards throughout her own career. Her transition from model to on-screen mentor and judge helped reinforce her lasting relevance in fashion and pop culture.

In 2019, Shimizu appeared in the fashion documentary House of Cardin, which chronicled the life and legacy of iconic designer Pierre Cardin. She offered reflections on the career of Hiroko Matsumoto, a pioneering Japanese model who inspired Shimizu’s own path. Her participation in the film tied her personal narrative to broader stories of Asian representation in global fashion history.

Most recently, Shimizu was featured in the documentary In Vogue: The 90s, where she reflected on her time as a top model, her impact on the industry, and her high-profile relationships with celebrities like Madonna and Angelina Jolie. The series gave her space to speak in her own words about her career, her relationships, and the significance of her gender expression during an era that rarely made room for women like her.

Through these varied appearances, Jenny Shimizu expanded her influence far beyond fashion. Her on-screen work helped build a legacy of queer visibility in entertainment and continued her mission of challenging and redefining public perceptions of gender and sexuality.

Modeling Agent Career and Fashion Design

In the late 2000s, Jenny Shimizu began shifting from high-profile modeling to working behind the scenes in the fashion industry. In 2010, she became a modeling agent at Women Direct, a boutique division of Women Management based in New York City. Her transition into the role of agent came after decades of firsthand experience navigating the modeling world as an out lesbian and a woman of color with an androgynous style.

Shimizu explained that becoming an agent allowed her to draw on all the lessons she had learned over the years. She moved back to New York to pursue the opportunity and quickly advanced in her new role. While most new agents take two to three years to begin booking clients, Shimizu was able to fast-track her success thanks to her extensive industry connections and personal reputation. She stated that she was able to get her models in front of the same clients she had worked for during her own modeling career.

Working at Women Direct allowed Shimizu to support new talent while promoting more inclusive standards in modeling. She emphasized the importance of authenticity and reminded young models not to take rejection personally. In her words, “A look and a type is something that people need. So they either need your look or they don’t. It is not something that you should take personally. It is just a business like anything else.”

In addition to her agency work, Shimizu also launched a fashion line that featured limited-edition T-shirt designs. The first batch quickly sold out, and she noted that she did not want to simply remake the same shirts over and over. Instead, she planned to design two new styles the following year, making the project more personal and deliberate.

Shimizu saw this move into fashion design as part of a broader trend among models to become brands and business owners in their own right. She explained that models were no longer just faces for hire, but icons who could create entire markets around their image and identity. Her approach to both fashion and business continued to reflect her values of individuality, resistance to conformity, and creative control.

Through both her agency work and her foray into fashion design, Shimizu remained a force within the industry. She helped open doors for younger models who, like her, did not fit the traditional mold. Her career shift was not a departure from her earlier success, but a continuation of her commitment to reshaping the modeling world from within.

Advocacy and Public Image

Jenny Shimizu has long been recognized not only for her trailblazing modeling career but also for her role as a visible, unapologetic lesbian and gender-nonconforming figure in mainstream media. From the beginning of her public life, she never hid her identity. She was one of the first models to be openly lesbian while still working in high fashion, a bold move in an industry that often discouraged anything outside of conventional femininity.

Shimizu has stated in interviews that she never viewed her sexuality or appearance as a hindrance. “You see me and you know I’m gay,” she said in a 2010 interview with AfterEllen. Rather than downplay what made her different, she embraced it as a strength. She believed that the more comfortable she was with herself, the easier it became for others to accept her. Her attitude helped shift how queer identity was perceived in fashion and media.

Her masculine presentation, love of motorcycles, tattoos, and refusal to conform to industry norms became central to her public image. Shimizu actively challenged ideas of what women in fashion could look like. Her success helped open doors for other gender-nonconforming and queer models, especially Asian American and butch-presenting individuals who were often excluded from beauty campaigns and runway shows.

In 2005, Shimizu took part in a symbolic protest for marriage equality. She participated in a staged wedding ceremony with television personality Rebecca Loos as part of the Sky documentary Power Lesbian UK, which was broadcast in the United States as Power Lesbians. The act was meant to protest America’s ban on same-sex marriage and to highlight the global movement for LGBTQ+ rights. The event received international attention and positioned Shimizu as not just a cultural figure but also a public advocate for queer equality.

Although she has not always identified as an activist in the traditional sense, Shimizu’s career has been inherently political. Her visibility in fashion, television, and film brought lesbian and Asian American representation to spaces where it was previously absent. She used her platform to normalize queerness and masculine-of-center identities in ways that were deeply personal and powerfully public.

Her continued openness about past relationships with high-profile women like Madonna and Angelina Jolie, and her reflections on being queer in the fashion industry, have helped to keep these conversations alive in both media and LGBTQ+ communities. Shimizu’s presence, confidence, and refusal to conform have left a lasting impact on public perceptions of identity, style, and representation.

Personal Life

Jenny Shimizu’s personal life has drawn public attention for decades, especially due to her romantic relationships with high-profile women during a time when queer relationships were still considered taboo in much of the entertainment industry. She has consistently spoken openly and unapologetically about her sexuality and experiences, becoming a rare example of a proud lesbian of color in the public eye throughout the 1990s and 2000s.

In the mid-1990s, Shimizu began a relationship with actress Angelina Jolie, whom she met while co-starring in the film Foxfire. Jolie has stated in interviews that she “fell in love with [Shimizu] the first second I saw her” and even said that she probably would have married her if she had not already married her husband at the time. Their romance became a prominent example of an openly queer relationship between two public figures and helped increase visibility for same-sex relationships in the media.

Around the same time, Shimizu was also in a romantic relationship with Madonna. In the documentary In Vogue: The 90s, Shimizu described their relationship as “crazy and fun” and full of spontaneity. She recalled receiving surprise calls from Madonna asking her to fly to locations like Paris in the middle of the night. Shimizu would often leave immediately to meet her, have an intimate encounter, and return to Milan to continue her modeling work. She later said the experience made her feel like a high-class escort but also called it exciting and unforgettable.

In 2005, Shimizu participated in a symbolic wedding ceremony with Rebecca Loos as part of the Sky documentary Power Lesbian UK. The televised event was a direct protest against the United States’ then-current ban on same-sex marriage. The two women were romantically involved following the broadcast, further connecting Shimizu’s personal life with her political beliefs about marriage equality.

In 2012, Shimizu met fashion consultant and cultural icon Michelle Harper at a party. The two quickly developed a relationship and were married in August 2014 in New York City. Their wedding was covered by major fashion publications including The New York Times and Harper’s Bazaar, which highlighted both their love and their shared place in the fashion world. The marriage marked a more private and stable period in Shimizu’s personal life, though the couple remained highly visible at fashion events and LGBTQ+ functions.

Shimizu has often reflected on her journey from a motorcycle mechanic in California to a global fashion figure. In interviews, she has said she hopes her younger self would be proud of how she lived her life. She believes in being honest, authentic, and unapologetic, and she encourages others to embrace what makes them different. For Shimizu, personal truth is a form of strength, and her relationships have always reflected that commitment.

Legacy and Cultural Impact

Jenny Shimizu holds a lasting place in both fashion and LGBTQ+ history as a trailblazer who shattered expectations around race, gender, and sexuality. Her emergence in the early 1990s marked a dramatic shift in what was possible for queer, gender-nonconforming, and Asian American individuals within the fashion industry.

She was one of the first Asian models to gain international prominence and the very first to walk in a Prada runway show. Her historic moment in 1993 as the first model of color to open a Prada show is widely viewed as a turning point for racial representation on the runway. At a time when mainstream fashion largely excluded Asian faces, Shimizu made space for herself and inspired others to follow.

Shimizu’s androgynous aesthetic, masculine presentation, tattoos, and bold lesbian identity directly challenged the hyper-feminine and Eurocentric ideals that dominated the modeling world. Unlike many of her peers, she did not conform to traditional beauty standards or hide her identity to succeed. She refused to grow out her hair, change her interests, or minimize her queerness. This refusal to compromise helped redefine the boundaries of fashion and what could be considered marketable or iconic.

Her work with Calvin Klein, Banana Republic, Jean Paul Gaultier, and Prada influenced a generation of fashion professionals, queer youth, and gender-nonconforming creatives. Designers like Calvin Klein embraced her authenticity at a time when few others would. She became a face of minimalist and unisex fashion that blurred gender lines before such trends were widely accepted.

Shimizu also became a pop culture icon thanks to her openness about her high-profile relationships. Her romances with Angelina Jolie and Madonna were not just tabloid fodder but cultural landmarks. They introduced mainstream audiences to a powerful, confident, and unapologetically queer woman of color who was navigating both fame and love on her own terms. These relationships, discussed publicly and candidly, helped shift conversations around bisexuality, lesbian identity, and visibility.

Beyond modeling and media appearances, Shimizu’s role as a mentor and modeling agent further deepened her influence. By guiding new models and offering them the kind of support she often had to fight for on her own, she helped reshape the industry from within. She used her knowledge and platform to open doors for others who, like her, did not fit into narrow industry molds.

Her staged wedding with Rebecca Loos in protest of the United States’ ban on same-sex marriage added a layer of activism to her public image. While she never centered herself as a political figure, her very presence in fashion and media was inherently political. She embodied the idea that queerness, Asian identity, and butch presentation were not obstacles but sources of power and originality.

Shimizu’s legacy lives on in the growing presence of openly queer, gender-diverse, and Asian models in fashion. Her story is often cited in documentaries, fashion retrospectives, and queer history projects. She remains an enduring symbol of what it means to be both true to oneself and to succeed on one’s own terms.

All Appearances and Work

Modeling and Fashion Campaigns

Calvin Klein CK One fragrance campaign
Calvin Klein Jeans campaign
Banana Republic “American Beauty” campaign
Jean Paul Gaultier runway and fashion shows
Anna Sui runway shows
Donna Karan runway shows
Prada Spring/Summer 1994 runway show (first Asian model and first model of color to open the show)
Numerous editorial spreads in Vogue, Out, DIVA, Curve, The Face, and i-D
T-shirt fashion line (limited run, sold out in 2010)

Film

Television

America’s Next Top Model (2005), guest appearance and mentor
Make Me a Supermodel, Season 2 (2009), judge
Dante’s Cove, Season 3 (2007), recurring character
Power Lesbian UK (2005), staged wedding with Rebecca Loos as protest performance
In Vogue: The 90s (2020s documentary), featured interview

Fashion Industry Work

Agent at Women Direct Modeling Agency (starting in 2010)
Mentor and scout for emerging models in New York
Public speaker and panelist at industry events focused on diversity in fashion

Media and Print Features

Interviews with AfterEllen, Out Magazine, Girlfriends, and Diva
Featured in queer visibility pieces on LGBTQ+ pioneers in fashion
Public relationship disclosures and cultural commentary featured in People, Harper’s Bazaar, and The New York Times

Activism and Advocacy Work

Same-sex marriage protest ceremony with Rebecca Loos
Outspoken visibility as a masculine-presenting lesbian and Asian American woman
Ongoing LGBTQ+ representation and public identity advocacy through media appearances and mentorship

Online Presence

Sources

Hargroder, Megan. “An Interview with Jenny Shimizu.” AfterEllen, Dec 14, 2010.
In Vogue: The 90s, documentary, 2020s.
“Jenny Shimizu.” Fashion Model Directory.
Fitzharris, Dustin. “Where Are They Now: Jenny Shimizu.” Out Magazine, 2010.
Halperin, Ian. Bad and Beautiful. Citadel Press, 2001.
Kregloe, Karman. AfterEllen review of Itty Bitty Titty Committee, 2007.
House of Cardin, documentary, 2019.
“Madonna’s Ex Jenny Shimizu…” People Magazine, 2024.
Trebay, Guy. “Michelle Harper, a Woman of Mystery.” NYT, 2013.
Kosin, Julie. “Fashion’s Favorite Risk-Taker Weds.” Harper’s Bazaar, 2014.
Czyzselka, Jane. “Jenny Shimizu & Rebecca Loos.” Diva, 2005.

Go Back

Index

Home

Jack of All Arts