Here’s an anniversary you may have missed: It has now been 20 years since the pop princess Britney Spears released her second studio album, Oops!…I Did It Again. On that famed record, the queen of the 2000s churned out some of her biggest hits, such as “Stronger” and “Lucky.” But it’s her lead single, with the same title as the album, that’s lodged most firmly in our memory and not just for its earworm-y chorus. The track’s space-age music video is downright iconic. When you think Spears, you think of that red latex jumpsuit. And in honor of the album’s anniversary, Vogue called up Estee Stanley, the video’s stylist, to reminisce about that now famous costume.
Stanley had a reputation for styling all of the hottest early-aughts pop artists—think Sugar Ray, Smash Mouth, and *NSYNC. (She styled the boy band’s videos “Bye Bye Bye” and “It’s Gonna Be Me.) She had also worked with the music video’s director, Nigel Dick, before. Stanley landed the job through that connection and the fact that at the time Spears was dating *NSYNC heartthrob Justin Timberlake.
Together, Stanley and Spears worked on crafting the initial fashion vision for the video’s space-age theme. “We wanted everything to be sexy and monochromatic,” Stanley says. They came up with all-white and all-black outfits for Spears, and Stanley dressed the backup dancers in silvery looks and sourced the astronaut costume for the hunky space boyfriend. (Fun fact: He is now a surgeon.)
But they couldn’t settle on anything for Spears’s main outfit. The red catsuit was barely a glimmer in their eyes. They turned to Michael Bush, a costume designer who was doing all of Spears’s custom tour looks at the time, to make something exciting for Spears. “It was a last-minute thing to go to him and see if he could make something for us,” Stanley says. “In [the music] world, everybody has to do everything in two minutes, so we knew he could pull it off. And he did.”
Bush had a little longer than two minutes to create something, but not much longer: He ended up creating the red latex suit overnight. Spears immediately loved it, though Stanley had initial reservations about the piece’s clingy material. “If you put a latex outfit on, you’re immediately sweating, and I knew she was going to be dancing all day,” says Stanley. “I was nervous that she would pass out.” The stylist’s fears were (partially) realized. “After one take, I unzipped her, and it literally looked like a bucket of water poured out of this jumpsuit. She had a very intense day, to say the least.”
The shooting day got even more intense. During a scene where Spears is lying down and the camera is pointed at her from above, a piece of the camera became dislodged and hit her on the back of the head. “But she was a trooper and went right back to work,” recalls Stanley. The video was one of Spears’s most acclaimed—bouffant ponytail and all.
More than two decades later, the stylist says working with Spears was one of her wildest, most fun projects. She still admires the singer’s razor-sharp creativity when it comes to her own look and videos and greatly attributes the success of “Oops!” to Spears’s initial vision. “Even with her little schoolgirl outfit [from ‘Baby One More Time’], she’s really set a precedent for always coming out in something very memorable,” Stanley says. “People didn’t expect it. She was still young and innocent, and then all of a sudden, she comes out in this vixen-y, sexy, skin-tight outfit. She definitely knew what she wanted and what she liked—that’s what makes her Britney.”
Originally Appeared on Vogue