Rachel Zoe’s First Freelance Styling Gig Was for Britney Spears’ ‘…Baby One More Time’ Video

Rachel Zoe, known for her work with Hollywood A-listers and her role on "The Real Housewives of Beverly Hills," has revealed that her very first freelance styling job was for Britney Spears’ iconic 1998 music video, "…Baby One More Time."

Zoe, 54, shared this detail in an interview with Page Six’s “Virtual Reali-Tea,” detailing how this early opportunity in her career came about while she was working at YM magazine. At the time, YM was a popular teen publication akin to Seventeen, placing Zoe at the epicenter of the late 1990s pop culture boom.

“My first-ever freelance job was working on [Britney Spears’ 1998 music video for] ‘…Baby One More Time,’” Zoe told Page Six. She explained that a colleague at YM, who frequently took on freelance projects, was unable to work on the Spears video and asked Zoe to cover for her. Zoe agreed, stepping in for one of the shooting days.

Prior to this freelance opportunity, Zoe had styled numerous pop stars and actors, including Gwen Stefani, during her tenure at YM magazine. The "…Baby One More Time" music video, which notably featured a then-16-year-old Spears in a schoolgirl ensemble, premiered in November 1998 and quickly became a cultural phenomenon.

While Zoe doesn't recall every detail of sourcing the now-famous wardrobe, she spoke about the realities of styling music videos with limited budgets during that era. "There were so many extras in these music videos that we were doing at the time that we would source … from everywhere," she said. This resourcefulness also contributed to her burgeoning love for vintage clothing.

Following her work on Spears’ video, Zoe continued to style other prominent artists of the late 1990s and early 2000s, including the Backstreet Boys, Enrique Iglesias, Jessica Simpson, and Ashlee Simpson.

More recently, Zoe has partnered with Aflac for its Check for Cancer campaign. As part of this initiative, she designed a limited-edition jacket featuring a custom checkered print with an embedded QR code. Scanning the code directs users to CheckForCancerNow.com, where Aflac's Cancer Screening Assessment Tool can help individuals determine recommended cancer screenings based on factors such as age and personal history.

Zoe expressed her enthusiasm for the campaign, stating, "Aflac approached me about doing this because detection for cancer and screenings for cancer are something that not enough people honestly know about, when they should do it." She aimed to create a fashion item that was both stylish and functional, making the message of cancer screening accessible and wearable.