With Danny and Evan Fashion exclusive Rachel Zoe reveals first freelance styling gig was for Britney Spears’ iconic ‘…Baby One More Time’ video By Evan Real and Danny Murphy Published Sep. 22, 2026, 1:48 p.m. ET Before Rachel Zoe was dressing Hollywood’s biggest celebrities — or starring on “The Real Housewives of Beverly Hills” — she was helping style one of pop music’s brightest breakout stars.
“My first-ever freelance job was working on [Britney Spears’ 1998 music video for] ‘…Baby One More Time,’” the 54-year-old exclusively revealed to Page Six’s “Virtual Reali-Tea.”
At the time, Zoe was still working at YM magazine, a teen publication in the vein of Seventeen, where she had a front-row seat to the pop-culture explosion of the late ’90s.
“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.”
Her foray into freelance styling came somewhat accidentally.
“[A colleague] at the magazine that I was working at did a lot of freelance work at the time. And 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.
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Zoe went on to work with Spears for a while, as well as a veritable who’s who of late-’90s and early-2000s pop royalty, including the Backstreet Boys, Enrique Iglesias, Jessica Simpson and Ashlee Simpson.
As for the now-iconic schoolgirl wardrobe in the “…Baby One More Time” video? Zoe doesn’t remember every detail of sourcing it — but she does remember the realities of styling music videos on a shoestring budget.
“God, I honestly don’t remember that,” she admitted of the Kmart-sourced wardrobe. “There were so many extras in these music videos that we were doing at the time that we would source … from everywhere.”
That resourcefulness also helped shape Zoe’s love of vintage.
“I would get all these vintage T-shirts and things like that,” she said.
Now, decades later, Zoe is using fashion for a very different — but equally important — purpose.
The designer has teamed up with Aflac as part of its Check for Cancer campaign, which aims to encourage people to learn more about recommended cancer screenings and have conversations with their health care providers.
Together, they created a limited-edition jacket featuring a custom checkered print with a QR code embedded directly into the design. A quick scan takes users to CheckForCancerNow.com, where they can use Aflac’s Cancer Screening Assessment Tool to learn more about screenings based on factors including their age and history.
“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.
For the fashion-forward star, making the message wearable was a no-brainer.
“I really thought about what style could be unisex and what is something easy that we can all wear?” she said.
And naturally, Zoe made sure the final look was more than just a fashion statement.
“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.”
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