Rachel Zoe has revealed that her very first freelance styling job came on one of the most famous music videos of the 1990s.
The 54-year-old said’s “Virtual Reali-Tea” podcast that she got her start working on Britney Spears’ 1998 debut video for “…Baby One More Time.” At that point, Zoe was still employed full-time at YM magazine, a teen publication similar to Seventeen, where she had watched the late-’90s pop explosion unfold from the front row.
“I’ve only had one job in my life [where] I had a boss, which was I worked at a magazine,” she said. “I worked with a lot of pop stars and actors like Gwen Stefani and blah, blah, blah. It all went on and on.”
The opportunity came through a colleague who had been juggling freelance work on the side. “She couldn’t do this job and so she asked me if I could cover for her and help her on one of the days [of shooting] and so I did,” Zoe recalled.
That single day of fill-in work launched what would become a long professional relationship with Spears, as well as a roster of late-’90s and early-2000s pop heavyweights. Zoe went on to style the Backstreet Boys, Enrique Iglesias, Jessica Simpson and Ashlee Simpson, among others.
The schoolgirl outfit that became one of the most recognizable looks in music video history — white button-down tied at the waist, plaid skirt, knee socks — remains somewhat hazy in Zoe’s memory. “God, I honestly don’t remember that,” she admitted when asked about sourcing the wardrobe from Kmart. “There were so many extras in these music videos that we were doing at the time that we would source … from everywhere.”
Those budget constraints did help forge one of Zoe’s lasting professional passions. “I would get all these vintage T-shirts and things like that,” she said, a practice that would shape her well-documented love of vintage fashion.
Decades removed from those lean music video productions, Zoe has redirected her fashion expertise toward a public health campaign. She has partnered with Aflac for its Check for Cancer initiative, which pushes people to learn about recommended cancer screenings and discuss them with their doctors.
“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,” Zoe explained.
The collaboration produced a limited-edition jacket with a custom checkered print and an embedded QR code that links to CheckForCancerNow.com. There, users can access Aflac’s Cancer Screening Assessment Tool to get personalized guidance based on age and medical history.
“I really thought about what style could be unisex and what is something easy that we can all wear?” she said.
The garment functions as both clothing and medical resource. “The print, the checkered print, the QR code’s embedded in it,” she said. “It’ll take you through a screening process that will tell you, based on your age and your history and all of these things, how to do a proper assessment and guide you through what you should do.”
The Spears video, directed by Nigel Dick and released in October 1998, catapulted the then-16-year-old Louisiana native to global stardom. The single topped charts in multiple countries and established the template for the teen pop boom that would dominate mainstream radio for the next several years. The visual’s Catholic schoolgirl aesthetic became instantly iconic, referenced and parodied repeatedly across the decades that followed.
Zoe currently appears on “The Real Housewives of Beverly Hills,” having joined the Bravo franchise in its fourteenth season.