Britney Spears Then and Now: Photos of Her Transformation – Hollywood Life

Britney Spears: Photos of the Pop Star From Her Teenage Years to Today

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December 1, 2023 2:02PM EST
Britney Spears
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Britney Spears is an undeniable pop music icon and you can celebrate her birthday with a look back at photos of her through the years, here.

Britney Spears became a worldwide phenomenon in the late 1990s and continued to release hit after hit through the 2000s. While her music career was unstoppable, Britney was dealing with a lot in her personal life. Mental health struggles lead to her conservatorship in 2008. The agreement left most of her personal decisions in the hands of her father, Jamie Spears.

She was released from the arrangement in late 2021 and has been happier than ever. In June 2022, she married her now-estranged husband, Sam Asghari. Despite their whirlwind romance, the two split in August 2023.

Britney’s had so many amazing moments over the years. Click through the gallery to see her various looks throughout her days in the business!

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Britney Spears Rehearsing at Arthur Ashe Kids’ Day

Britney Spears Rehearsing at Arthur Ashe Kids’ Day
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Britney Spears hit the stage for a rehearsal at Arthur Ashe Kids’ Day in 1999. She dressed for the times in stretchy pants and an Abercrombie t-shirt.

April 20, 2020, 9:42AM
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Britney Spears at Disney World

Britney Spears at Disney World
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Britney Spears was all smiles while making an appearance in Disney World in 1999. She wore sunglasses and a hot pink top while at the park.

April 20, 2020, 9:42AM
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Britney Spears Performing at Zootopia

Britney Spears Performing at Zootopia
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Britney Spears performed at the Z100 Zootopia Concert in June 1999. She wore her signature belly shirt and put her abs on display in a crop top and low-waisted pants.

April 20, 2020, 9:42AM
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Britney Spears at the 1999 Billboard Music Awards

Britney Spears at the 1999 Billboard Music Awards
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Britney Spears looked adorable at the 1999 Billboard Music Awards in Las Vegas. She wore a light purple dress and a white shawl, and styled her hair in a straight style.

April 20, 2020, 9:42AM
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Britney Spears Performing in Disney World

Britney Spears Performing in Disney World
Larry Marano/Shutterstock

Britney Spears sang and danced onstage while performing at Disney World in 1999. She wore cargo pants and a purple tank top for the performance.

April 20, 2020, 9:42AM
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Britney Spears Performing in Florida

Britney Spears Performing in Florida
Larry Marano/Shutterstock

Britney Spears gave a performance in Florida in June 1999. She rocked a latex tube tob and white pants, putting her tanned abs on display, with her hair in a ponytail. 

April 20, 2020, 9:42AM
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Britney Spears at the 1999 MTV VMAs

Britney Spears at the 1999 MTV VMAs
Stephen Chernin/AP/Shutterstock

Britney Spears showed off her dance moves while hitting the stage at a rehearsal for the MTV Video Music Awards. She wore black pants and a red top, while sweating it out with her hair in a ponytail.

April 20, 2020, 9:42AM
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Britney Spears Performing in Ohio

Britney Spears Performing in Ohio
Shutterstock

Britney Spears showed off sexy dance moves while performing in 2001. She wore an all-black ensemble, and showed off her abs while lifting up her shirt during the dance.

April 20, 2020, 9:42AM
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Britney Spears at the 2001 Teen Choice Awards

Britney Spears at the 2001 Teen Choice Awards
Lucy Nicholson/AP/Shutterstock

Britney Spears took the stage to accept an award at the 2001 Teen Choice Awards. She looked so cute in her denim outfit, which she covered up in a white caridgan.

April 20, 2020, 9:42AM
10 of 23

Britney Spears & Justin Timberlake Posing

Britney Spears & Justin Timberlake Posing
Mark J Terrill/AP/Shutterstock

Britney Spears and Justin Timberlake attended the 2001 American Music Awards as a couple. They wore their iconic, matching denim outfits on the red carpet at the event.

April 20, 2020, 9:42AM
11 of 23

Britney Spears Performing at the 2001 VMAs

Britney Spears Performing at the 2001 VMAs
Beth A Keiser/AP/Shutterstock

Britney Spears transformed into a young woman with her sexy performance at the 2001 VMAs. She famously showed off her hot body and danced with a snake onstage.

April 20, 2020, 9:42AM
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Britney Spears Promoting Her 2003 Album

Britney Spears Promoting Her 2003 Album
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Britney Spears promoted her 2003 album ‘In The Zone’ at an appearance in New York City. She wore a halter top and jeans, with a white belt.

April 20, 2020, 9:42AM
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Britney Spears at the 2004 Billboard Music Awards

Britney Spears at the 2004 Billboard Music Awards
Joe Cavaretta/AP/Shutterstock

Britney Spears was all smiles while presenting at the 2004 Billboard Music Awards. She wore a sheer ensemble and her hair in a ponytail.

April 20, 2020, 9:42AM
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Britney Spears Performing on ‘GMA’

Britney Spears Performing on ‘GMA’
Charles Sykes/Shutterstock

Britney Spears gave an epic performance on Good Morning America in 2008. She rocked high-waisted shorts and a red crop top, putting her abs and legs on display.

April 20, 2020, 9:42AM
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Britney Spears Onstage at the 2008 VMAs

Britney Spears Onstage at the 2008 VMAs
Kevork Djansezian/AP/Shutterstoc

Britney Spears accepted an award at the 2008 Video Music Awards. She looked so cute in her sparkly fringe dress with her hair in curls.

April 20, 2020, 9:42AM
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Britney Spears Performing During the Femme Fatale Tour

Britney Spears Performing During the Femme Fatale Tour
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Britney Spears hit the stage in Paris to perform during her Femme Fatale tour in 2011. She wore a black and pink lingerie ensemble, along with mesh tights and a choker.

April 20, 2020, 9:42AM
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Britney Spears at ‘The X-Factor’ Premiere

Britney Spears at ‘The X-Factor’ Premiere
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Britney Spears attended ‘The X-Factor’ premiere in 2012. She was a judge on the show and looked gorgeous in her blue dress with printed design.

April 20, 2020, 9:42AM
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Britney Spears at ‘The X-Factor’ Finale

Britney Spears at ‘The X-Factor’ Finale
Jim Smeal/BEI/Shutterstock

Britney Spears spoke with reporters at ‘The X-Factor’ finale in 2012. She wore a low-cut black dress and dark makeup, with her hair pulled back.

April 20, 2020, 9:42AM
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Britney Spears Performing at Jingle Ball

Britney Spears Performing at Jingle Ball
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Britney Spears hit the stage and dances during her 2016 Jingle Ball performance in Los Angeles. She bared her abs in a tiny top and short shorts, paire with thigh-high boots.

April 20, 2020, 9:42AM
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Britney Spears Performing in Taiwan

Britney Spears Performing in Taiwan
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Britney Spears performed in Taiwan in June 2017. She wore a green bodysuit, along with tights and thigh-high boots.

April 20, 2020, 9:42AM
21 of 23

Britney Spears at ‘The X-Factor’ Finale

Britney Spears at ‘The X-Factor’ Finale
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Britney Spears attended night one of ‘The X-Factor’ finale in 2012. She wore a black outfit and was all smiles on the red carpet.

April 20, 2020, 9:42AM
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Britney Spears at the GLAAD Media Awards

Britney Spears at the GLAAD Media Awards
Matt Baron/Shutterstock

Britney Spears attended the GLAAD Media Awards in 2018. She wore a sexy fringed dress, which featured side cutouts and a lowcut neckline.

April 20, 2020, 9:42AM
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Britney Spears at the ‘Once Upon a Time In Hollywood’ Premiere

Britney Spears at the ‘Once Upon a Time In Hollywood’ Premiere
Rob Latour/Shutterstock

Britney Spears attended the ‘Once Upon a Time In Hollywood’ premiere in 2019. She wore a one-shouldered red dress and black heels on the carpet.

April 20, 2020, 9:42AM
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