The Biggest Fashion Moments from the Britney Spears Memoir — And What They Reveal About the Pop Star

It’s been nearly a week since Britney Spears released her highly-anticipated novel, “The Woman in Me,” a tome that has already reportedly become the highest selling celebrity memoir in history on just its first day of release (according to the pop star herself).

Fans and readers may still be mulling over juicy details and revelations on ex Justin Timberlake — and shocking insights on Spears’s conservatorship. But within the pages, the memoir is also chock full of fashion and style moments from the pop star, who first broke onto the scene in 1999 with “Hit Me Baby One More Time” and came to dominate the early aughts and its MTV “TRL” scene.

Spears has never pretended to be part of the inner circle of the celebrity fashion machine — or even interested in it all that much (“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,” she wrote). But throughout her memoir, key fashion moments that the pop stars chooses to include are instrumental at illustrating the book’s central themes, of control (and loss of it), of the public’s claim to the pop star’s body, of a refusal to conform to expectations from both her family and pop culture writ large, and of self expression as part of Spears’s search for freedom.

The pop star had plenty to say on everything from her hair (and why she infamously shaved it off in 2007) to her notorious denim couple’s look with Timberlake. She also explained why she keeps posting Instagram fashion selfies and dances — and doesn’t care what everyone thinks of them.

Here, a selection of key fashion moment’s from “The Woman in Me,” and how they reveal the tension Spears felt as a pop star and public figure.

Britney broke a heel while walking home from a NYC club in 2002, post-Justin Timberlake breakup

In the aftermath of her breakup with Timberlake, Spears said she spent a lot of time in New York, living in a four-story apartment — Cher’s former pad — in the city’s Noho neighborhood. Save for rare outings, the pop star said she was confined to the home, especially when she found herself without a key to the apartment.

“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.”

The pop star partied with Donatella Versace in Milan — then picked up a mysterious stranger

Spears also traveled to Europe in the aftermath of her breakup with Timberlake, recalling Milan Fashion Week festivities.

“To get my confidence back, in September 2002 I went to Milan to visit Donatella Versace. That trip invigorated me — it reminded me that there was still fun to be had in the world,” Spears wrote.

“Eventually we started talking, and I decided I’d like to have drinks with him at my hotel. We headed to my car, but during the drive, he did something that just turned me off…. so I told the driver to pull over, and without saying a word, I kicked the guy out on the side of the road and left him there.”

The infamous denim couple’s outfit was Britney’s idea

The denim-on-denim couple’s look from Spears and Timberlake at the 2001 American Music. Awards is the stuff of pop culture infamy (and many a Halloween getup). The pop star revealed that she was inspired by Southern traditions of mothers dressing their children in coordinating outfits for church for the denim outfits the duo wore.

“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 wrote.

“I’m always happy to see it parodied as a Halloween costume. I’ve heard Justin get flak for the look.”

The snake she wore while performing at the 2001 MTV VMAs hissed at her onstage

“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,” the pop star wrote of the infamous performance, often considered a high point of her career. “You didn’t see that shot on TV, but in real life? I was thinking, ‘Are you fucking serious right now?’

Britney knew the power of hair in her public image

“My long hair was a big part of what people liked — I knew that…. Shaving my head was my way of saying to the world: Fuck you. You want me to be pretty for you? Fuck you. You want me to be good for you? Fuck you. You want me to be your dream girl? Fuck you. I’d been the good girl for years. I’d smiled politely while TV show hosts leered at my breasts, American parents said I was destroying their children by wearing a crop top.”

Later, Spears recalled how she used her hair once again to push back against her family and conservators as they ramped up her tour and performance schedule.

“As performers, we girls have our hair. That’s the real thing guys want to see… They want you the thrash it,” she writes. “Everyone who was making money off me wanted me to move my hair, and I knew it — and so I did everything but that.”

She hated her 2007 MTV VMAs outfit

“There was a problem with my costume and with my hair extensions,” wrote Spears of her 2007 MTV Video Music Awards performance, which resulted in plenty of negative criticism in the media and even questioning from Ryan Seacrest if she was fit to be a mother.

“I hadn’t slept the night before. I was dizzy. It was less and a year since I’d had my second baby in two years but everyone was acting like my not having six-pack abs was offensive,” she recalled.

“I could see myself on video throughout the auditorium while I performed; it was like looking at myself in a fun-house mirror…. As performers we all have bad nights. They don’t usually have consequences so extreme.”

The Instagram fashion shows and nude selfies are part of reclaiming her identity

“The first step toward securing my freedom was for people to begin to understand that I was still a real person — and I knew that I could do that by sharing more of my life on social media,” wrote Spears in one of the last chapters of the memoir, as she recounted the steps she took to end her conservatorship.

The lo-fi fashion shows and video selfies may have been key for Spears to keep her fans and supporters engaged during the legal proceedings that led to the conservatorship’s dissolution — but for the pop star, the social media postings are also a way for her to reclaim her identity and her body.

“I know that a lot of people don’t understand why I love taking pictures of myself naked or in new dresses,” she wrote in the book’s last chapter. “But I think if they’d been photographed by other people thousands of times, prodded and posed for other people’s approval, they’d understand that I get a lot of joy from posing the way I feel sexy and taking my own picture, doing whatever I want with it.”