• Britney Spears, in a pink sheath dress, attends the American Music Awards on January 26, 1998 at the Shrine Auditorium, in Los Angeles, California. Getty Images
    Britney Spears, in a pink sheath dress, attends the American Music Awards on January 26, 1998 at the Shrine Auditorium, in Los Angeles, California. Getty Images
  • Britney Spears, in black trousers and a cropped short-sleeved top, attends a Tommy Hilfiger party on July 7, 1999 in New York, US. Getty Images
    Britney Spears, in black trousers and a cropped short-sleeved top, attends a Tommy Hilfiger party on July 7, 1999 in New York, US. Getty Images
  • Britney Spears, in a frilled pink cropped top, attends the Silicon CDDB Awards in Los Angeles, California, on August 3, 1999. Getty Images
    Britney Spears, in a frilled pink cropped top, attends the Silicon CDDB Awards in Los Angeles, California, on August 3, 1999. Getty Images
  • Britney Spears, in sequinned trousers, attends the Teen Choice Awards in Los Angeles, California, on August 1, 1999. Getty Images
    Britney Spears, in sequinned trousers, attends the Teen Choice Awards in Los Angeles, California, on August 1, 1999. Getty Images
  • Britney Spears, in a metallic jacket and lizard-print trousers, attends the MTV Video Music Awards in New York, US, on September 9, 1999. Getty Images
    Britney Spears, in a metallic jacket and lizard-print trousers, attends the MTV Video Music Awards in New York, US, on September 9, 1999. Getty Images
  • Britney Spears, in a spaghetti-strapped dress and pashmina, attends the Billboard Music Awards in Las Vegas, Nevada, on December 8, 1999. Getty Images
    Britney Spears, in a spaghetti-strapped dress and pashmina, attends the Billboard Music Awards in Las Vegas, Nevada, on December 8, 1999. Getty Images
  • Britney Spears, in embroidered flares and a halter-neck, attends a Grammys photo shoot in Los Angeles, California, on February 21, 2000. Getty Images
    Britney Spears, in embroidered flares and a halter-neck, attends a Grammys photo shoot in Los Angeles, California, on February 21, 2000. Getty Images
  • Britney Spears, in Randolph Duke, arrives at the 42nd annual Grammy Awards in Los Angeles, California, on February 23, 2000. Getty Images
    Britney Spears, in Randolph Duke, arrives at the 42nd annual Grammy Awards in Los Angeles, California, on February 23, 2000. Getty Images
  • Britney Spears, in a fringed pink mini, attends the Teen Choice Awards in Santa Monica, California, on August 6, 2000. Getty Images
    Britney Spears, in a fringed pink mini, attends the Teen Choice Awards in Santa Monica, California, on August 6, 2000. Getty Images
  • Britney Spears, in an orange and pink lace-trimmed coat with matching fedora, attends the Billboard Music Awards in Las Vegas, Nevada, on December 5, 2000. Getty Images
    Britney Spears, in an orange and pink lace-trimmed coat with matching fedora, attends the Billboard Music Awards in Las Vegas, Nevada, on December 5, 2000. Getty Images
  • Britney Spears and Justin Timberlake, in matching double denim, arrive at the 28th annual American Music Awards at the Shrine Auditorium in Los Angeles, California, on January 8, 2001. Reuters
    Britney Spears and Justin Timberlake, in matching double denim, arrive at the 28th annual American Music Awards at the Shrine Auditorium in Los Angeles, California, on January 8, 2001. Reuters
  • Justin Timberlake and Britney Spears, in a light taupe slip dress, attend an event at the Regent Beverly Wilshire Hotel in Beverly Hills, California, on April 1, 2001. Getty Images
    Justin Timberlake and Britney Spears, in a light taupe slip dress, attend an event at the Regent Beverly Wilshire Hotel in Beverly Hills, California, on April 1, 2001. Getty Images
  • Britney Spears, in a strapless denim dress and polka-dot blouse, attends a photo call for the film 'Crossroads' in Amsterdam, the Netherlands, on March 19, 2002. EPA
    Britney Spears, in a strapless denim dress and polka-dot blouse, attends a photo call for the film 'Crossroads' in Amsterdam, the Netherlands, on March 19, 2002. EPA
  • Britney Spears, in a sheer blouse and patterned skirt, attends a photo call for 'Crossroads' at Hotel Palace on March 21, 2002 in Madrid, Spain. Getty Images
    Britney Spears, in a sheer blouse and patterned skirt, attends a photo call for 'Crossroads' at Hotel Palace on March 21, 2002 in Madrid, Spain. Getty Images
  • Britney Spears, in an asymmetric silver dress, arrives at the premiere of 'Crossroads' on March 25, 2002 in London, England. Getty Images
    Britney Spears, in an asymmetric silver dress, arrives at the premiere of 'Crossroads' on March 25, 2002 in London, England. Getty Images
  • Britney Spears, in jeans and a lace blouse, attends the premiere of 'Crossroads' at Fox Studio in Sydney, Australia, on April 18, 2002. Getty Images
    Britney Spears, in jeans and a lace blouse, attends the premiere of 'Crossroads' at Fox Studio in Sydney, Australia, on April 18, 2002. Getty Images
  • Britney Spears, in stripes and cowboy boots, attends a Barbie Award ceremony on April 21, 2002 in Tokyo, Japan. Getty Images
    Britney Spears, in stripes and cowboy boots, attends a Barbie Award ceremony on April 21, 2002 in Tokyo, Japan. Getty Images
  • Britney Spears, in a nude-toned slip dress, poses with one of her outfits which will be auctioned for charity during a press preview in New York, US, on May 22, 2003. EPA
    Britney Spears, in a nude-toned slip dress, poses with one of her outfits which will be auctioned for charity during a press preview in New York, US, on May 22, 2003. EPA
  • Britney Spears, in a white corseted dress, attends the MTV Video Music Awards at Radio City Music Hall in New York, US, on August 28, 2003. EPA
    Britney Spears, in a white corseted dress, attends the MTV Video Music Awards at Radio City Music Hall in New York, US, on August 28, 2003. EPA
  • Britney Spears, in jeans and a faux fur jacket, attends a Hollywood Walk of Fame ceremony in Los Angeles, California, on November 17, 2003. EPA
    Britney Spears, in jeans and a faux fur jacket, attends a Hollywood Walk of Fame ceremony in Los Angeles, California, on November 17, 2003. EPA
  • Britney Spears, in a fluffy oversized jacket and jeans, attends a press conference to promote her album 'In the Zone' on December 12, 2003 in Tokyo, Japan. Getty Images
    Britney Spears, in a fluffy oversized jacket and jeans, attends a press conference to promote her album 'In the Zone' on December 12, 2003 in Tokyo, Japan. Getty Images
  • Britney Spears, in Roberto Cavalli, arrives at the NRJ Music Awards at the Palais des Festivals on January 24, 2004 in Cannes, France. Getty Images
    Britney Spears, in Roberto Cavalli, arrives at the NRJ Music Awards at the Palais des Festivals on January 24, 2004 in Cannes, France. Getty Images
  • Britney Spears, in a satin skirt suit, attends the Baby Phat fashion show at Mercedes-Benz Fashion Week in New York, US, on February 2, 2007. Shutterstock
    Britney Spears, in a satin skirt suit, attends the Baby Phat fashion show at Mercedes-Benz Fashion Week in New York, US, on February 2, 2007. Shutterstock
  • Britney Spears, in a white mini and straw trilby, arrives at the opening of LAX Nightclub at the Luxor Resort & Casino on September 1, 2007 in Las Vegas, Nevada. Getty Images
    Britney Spears, in a white mini and straw trilby, arrives at the opening of LAX Nightclub at the Luxor Resort & Casino on September 1, 2007 in Las Vegas, Nevada. Getty Images
  • Britney Spears, in a feather-trimmed bodysuit, attends the Bambi Awards on November 27, 2008 in Offenburg, Germany. Getty Images
    Britney Spears, in a feather-trimmed bodysuit, attends the Bambi Awards on November 27, 2008 in Offenburg, Germany. Getty Images
  • Britney Spears, in a shimmering LBD, arrives at the Teen Choice Awards at Gibson Amphitheatre on August 9, 2009 in Universal City, California. AFP
    Britney Spears, in a shimmering LBD, arrives at the Teen Choice Awards at Gibson Amphitheatre on August 9, 2009 in Universal City, California. AFP
  • Britney Spears, in a pink chiffon mini dress, attends the premiere of 'Toy Story 3' on June 13, 2010 at the El Capitan Theatre in Hollywood, California. Shutterstock
    Britney Spears, in a pink chiffon mini dress, attends the premiere of 'Toy Story 3' on June 13, 2010 at the El Capitan Theatre in Hollywood, California. Shutterstock
  • Britney Spears, in Moschino, and Jason Trawick attend the MTV Video Music Awards at the Nokia Theatre in Los Angeles, California, on August 28, 2011. EPA
    Britney Spears, in Moschino, and Jason Trawick attend the MTV Video Music Awards at the Nokia Theatre in Los Angeles, California, on August 28, 2011. EPA
  • Britney Spears, in Topshop, attends her UK tour launch party at Sanctum Soho on September 16, 2011 in London, England. Getty Images
    Britney Spears, in Topshop, attends her UK tour launch party at Sanctum Soho on September 16, 2011 in London, England. Getty Images
  • Britney Spears, in Herve Leger, and her son, Sean Federline, attend the premiere of 'Smurfs 2' in Westwood, California, on July 28, 2013. EPA
    Britney Spears, in Herve Leger, and her son, Sean Federline, attend the premiere of 'Smurfs 2' in Westwood, California, on July 28, 2013. EPA
  • Britney Spears, in Mikael D, attends the 40th People's Choice Awards at the Nokia Theatre in Los Angeles, California, on January 8, 2014. EPA
    Britney Spears, in Mikael D, attends the 40th People's Choice Awards at the Nokia Theatre in Los Angeles, California, on January 8, 2014. EPA
  • Britney Spears, in Tadashi Shoji, promotes her Dessous collection, The Intimate Britney Spears, at Gatta boutique in Warsaw, Poland, on September 24, 2014. EPA
    Britney Spears, in Tadashi Shoji, promotes her Dessous collection, The Intimate Britney Spears, at Gatta boutique in Warsaw, Poland, on September 24, 2014. EPA
  • Britney Spears, in Michael Costello, promotes her Dessous collection, The Intimate Britney Spears, at Centro mall on September 25, 2014 in Oberhausen, Germany. Getty Images
    Britney Spears, in Michael Costello, promotes her Dessous collection, The Intimate Britney Spears, at Centro mall on September 25, 2014 in Oberhausen, Germany. Getty Images
  • Britney Spears, in Yousef Al Jasmi, arrives for the Billboard Music Awards at the MGM Grand Hotel and Casino in Las Vegas, Nevada, on May 17, 2015. EPA
    Britney Spears, in Yousef Al Jasmi, arrives for the Billboard Music Awards at the MGM Grand Hotel and Casino in Las Vegas, Nevada, on May 17, 2015. EPA
  • Britney Spears, in Mikael D, attends the Teen Choice Awards at the Galen Centre in Los Angeles, California, on August 16, 2015. EPA
    Britney Spears, in Mikael D, attends the Teen Choice Awards at the Galen Centre in Los Angeles, California, on August 16, 2015. EPA
  • Britney Spears, in Labourjoisie, attends the 32nd MTV Video Music Awards at the Microsoft Theatre in Los Angeles, California, on August 30, 2015. EPA
    Britney Spears, in Labourjoisie, attends the 32nd MTV Video Music Awards at the Microsoft Theatre in Los Angeles, California, on August 30, 2015. EPA
  • Britney Spears, in Julien MacDonald, attends the 33rd MTV Video Music Awards at Madison Square Garden in New York, US, on August 28, 2016. EPA
    Britney Spears, in Julien MacDonald, attends the 33rd MTV Video Music Awards at Madison Square Garden in New York, US, on August 28, 2016. EPA
  • Britney Spears, in Nookie Charm, and Sam Asghari attend the premiere of 'Once Upon a Time... In Hollywood' at the TCL Chinese Theatre in Los Angeles, California, on July 22, 2019. EPA
    Britney Spears, in Nookie Charm, and Sam Asghari attend the premiere of 'Once Upon a Time... In Hollywood' at the TCL Chinese Theatre in Los Angeles, California, on July 22, 2019. EPA

Britney Spears's style evolution in 38 photos: from '90s pop princess to queen of the charts


Emma Day
  • English
  • Arabic

If you could encapsulate Noughties fashion in one image, it's surely Britney Spears and then-boyfriend Justin Timberlake rocking matching double denim to the 2001 American Music Awards.

And that's not the only early millennia trend that Spears helped bring to the fashion forefront.

Whether it's boot-cut jeans on the red carpet, oversized fluffy jackets, strappy slip dresses on sequin-encrusted mini dresses, the American singer was, arguably, the fashion compass at the start of the 21st century.

However, the Oops ... I Did It Again star has, over the years, embraced a more contemporary aesthetic, ditching her shimmering minis for sleek separates and demure maxis.

Whether donning high street favourites such as Topshop, designer labels including Roberto Cavalli or regional stars such as Kuwait's Yousef Al Jasmi, Spears is no stranger to a bit of glamour, often enlivening awards ceremonies and premieres with a little sparkle.

Here, we take a look at how the star's style has evolved throughout her time in the spotlight.

Scroll through the gallery above to see more images of Britney Spears through the years.