Britney Bares All: The Pop Icon’s Most Revealing Fashion Moments
Britney Spears has never pretended to be part of the celebrity fashion inner circle. “I never knew how to play the game. I didn’t know how to present myself on any level. I was a bad dresser – hell, I’m still a bad dresser,” the pop icon writes in her new bombshell memoir, The Woman in Me.
But throughout the book’s pages, Spears’ fashion moments reveal so much more than meets the eye. Her style choices illustrate the memoir’s central themes – control, freedom, conformity, and self-expression. From her breakout denim look with Justin Timberlake to her innate bond with snakes, Spears’ fashion sensibility has always spoken volumes.
In the aftermath of her painful breakup with Timberlake, Spears spent time recovering in New York. Confined in Cher’s former Noho apartment, her rare nights out provided a dose of freedom. “One night I put on a $129 Bebe dress and high heels, and my cousin took me to a sexy underground club with low ceilings and red walls. I took a couple hits from a joint, my first time smoking pot. Later, I walked all the way home so I could take in the city, breaking one of my heels along the way,” she reveals. A glitzy dress and broken heel capture her fleeting taste of independence.
Perhaps no look is more iconic than the matching denim ensemble Spears and Timberlake wore to the 2001 American Music Awards. The pop star explains she drew inspiration from Southern church traditions of mothers dressing their kids in matching outfits. “At first, honestly, I thought it was a joke. I didn’t think my stylist was actually going to do it, and I never though Justin was going to do it with me. But they both went all in,” she admits. “I’m always happy to see it parodied as a Halloween costume. I’ve heard Justin get flak for the look.” In matching Timberlake in denim, Spears challenged fashion norms in her own subtle, subversive way.
Spears’ legendary snake performance at the 2001 MTV Video Music Awards was a defining fashion moment. “What nobody knows is that as I was singing, the snake brought its head right around to my face, right up to me, and started hissing at me. You didn’t see that shot on TV, but in real life? I was thinking, ‘Are you f***ing serious right now?’” While the python’s hiss rattled Spears, she didn’t let her fear show. The allure of a bare-shouldered Spears with a snake across her shoulders encapsulated the allure and danger of the pop star image.
Today, Spears still uses fashion as self-expression, regularly posting Instagram outfits and dances. “I know a lot of people feel like I should stop posting my looks or my little dance routines…But you know what? I’m not gonna stop,” she asserts. “This is who I am. This makes me happy. And free.” From denim to diamonds, snakeskin to sequins, Spears’ style will always tell her story, on her own terms.
