Britney Spears’ Style Evolution Through the Years: From ‘Baby One More Time’ Era to Her Last Red Carpet Appearance

Global pop star Britney Spears debuted her memoir “The Woman in Me” on Tuesday, to the celebration of many fans who have waited for her to tell the story of her multidecade career and what happened during her conservatorship. The memoir includes bombshell stories surrounding her relationship with Justin Timberlake, her family dynamic and her career.

Spears has been in the public eye since the ’90s when she was a teenager. Since the music video for her debut single “Baby One More Time” and her infamous schoolgirl uniform, Spears’ style has been under a microscope.

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Over the years, she’s transformed her image from the girl next door to Hollywood-ready for red carpets. Here, WWD takes a closer look at Britney Spears’ style through the years.


Britney Spears (Photo by Kevin Mazur Archive/WireImage)
Britney Spears

At a 1998 Jingle Ball event, Spears showcased a classic girl-next-door image. The pop star, who was still early in her career, wore a gray cardigan, white tube top, khaki pants and brown desert boots. At this point, Spears was making waves for her song “Baby One More Time.”


Britney Spears at the Staples Center in Los Angeles, California (Photo by Kevin Mazur/WireImage)
Britney Spears at the 42 annual Grammy Awards.

At the 2000 Grammy Awards, Spears was nominated for Best New Artist, ultimately losing to Christina Aguilera. For the momentous career milestone, Spears donned an ethereal ensemble, including a white slip dress and a white fur shawl. She completed her look with a diamond necklace.


Britney Spears   (Photo by Chris Polk/FilmMagic)
Britney Spears performing at the 2001 VMAs.

One of Spears’ most iconic outfits is her 2001 VMAs look where her ultimate accessory was an albino Burmese python. Spears’ apparel for the evening included a green cutout bra top with pink gemstones. The top was paired with low-rise HotPants with a butterfly motif and a bejeweled waistline. Multiple sea green colored scarves were attached to the shorts, which swayed while she danced.


(EXCLUSIVE, Premium Rates Apply) Britney Spears  **EXCLUSIVE** (Photo by Kevin Mazur/WireImage)
Britney Spears at the 2006 Teen Choice Awards.

In 2006, at the Teen Choice Awards, Spears was just a month away from giving birth to her second son, Jayden James. The singer rocked maternity style wearing a chiffon minidress paired with nude Christian Louboutin heels. Although known for her blonde hair, Spears’ hair was dyed jet-black at the event.


AUSTIN, TX - MAY 24:  Singer Britney Spears walks the red carpet before the first day of taping the second season of The X Factor auditions for which she is a judge at The Frank Erwin Center on May 24, 2012 in Austin, Texas.  (Photo by Gary Miller/WireImage)

Britney Spears spent one season as a judge on “The X Factor” in 2012. As she stepped into the role of a judge, Spears’ style began to shift. She began wearing elevated mini and midi dresses, like the bright pink minidress she wore to one of the show’s tapings.


LOS ANGELES , CA - DECEMBER 02: Britney Spears performs on stage during the 102.7 KIIS FM's Jingle Ball 2016 on December 02, 2016 in Los Angeles, California.  (Photo by JB Lacroix/WireImage)
Britney Spears performs onstage during the 102.7 KIIS FM’s Jingle Ball 2016 on Dec. 2, 2016, in Los Angeles.

Throughout the 2010s, Spears developed a love for sparkles when it came to both her outfits onstage and the red carpet. At the 2016 Jingle Ball, Spears wore a sparkling black blazer dress with feather sleeves. She completed the look with fishnet tights and black thigh-high boots.


Britney Spears and Sam Asghari
Britney Spears and Sam Asghari

At one of Spears’ last red carpet appearances, she and her then-fiancé Sam Asghari attended the premiere of “Once Upon a Time…in Hollywood” in Los Angeles. Spears wore a red minidress with peep-toe ankle-strap black pumps. Asghari wore a tan suit with a white shirt, skinny black tie and black loafers.

Launch Gallery: Britney Spears' Style Evolution Through the Years

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