- From the minute she burst on the scene with “Baby One More Time” in 1998, Britney Spears has delivered a number of iconic looks.
- Spears evolved from the pretty pastels she favoured as a teen to an edgier aesthetic as she became more comfortable experimenting with styles.
- There were plenty of famous stage looks as well, from her famous python to that crystal-encrusted bodysuit.
- In honour of her birthday, here are 40 of the pop icon’s most memorable looks.
- Visit Insider’s homepage for more stories.
From denim dresses to glamorous red carpet gowns, Britney Spears has experimented with plenty of looks since storming on the pop scene.
Ahead of the star’s 38th birthday on December 2, we’ve gathered some of her best red-carpet and on-stage outfits to celebrate the occasion.
Looking back, it’s interesting to see Spears’ transition from wearing pop princess pastels in the late ’90s to edgier outfits in the 2000s and 2010s.
See some of her most memorable looks below.
At the beginning of her mega-stardom in January 1999, then 17-year-old Britney Spears attended the American Music Awards in a pink dress.
Spears kept her hair a more natural brunette colour rather than the bleach blonde locks that have become her signature style.
She performed onstage wearing a neon pink top and sneakers in June 1999.
The head mic really completes the ’90s aesthetic.
She then opted for sparkly pants and a light pink top while attending the Teen Choice Awards in August 1999.
Spears would soon ditch her pop princess aesthetic for slightly edgier outfits.
Two months later in September, Spears wore snakeskin-style pants with a shiny top and jacket.
She accessorized with metallic accessories.
After turning 18 in December 1999, she walked the red carpet of the Billboard Music Awards in a lilac gown and white shawl.
This was the pop star’s most classically elegant look yet.
Spears went with a similar dress for her appearance at the Grammys in February 2000.
She wore a sleek white Randolph Duke gown and Oscar de la Renta fur stole.
Spears opted for this light pink, fringed dress that went perfectly with the beach theme at the 2000 Teen Choice Awards in August.
She took home the award for choice female artist.
The pop star’s crystal-encrusted bodysuit for the 2000 MTV Video Music Awards caused quite a stir that September.
It has since become one of the singer’s most famous outfits.
Spears, then 19, arrived to the 2000 Billboard Music Awards in December wearing this eccentric orange and purple ensemble.
The boots and feathered fedora really took the look to the next level.
Spears wore a patchwork denim dress while her then-boyfriend, Justin Timberlake, wore a matching denim suit on the red carpet in January 2001.
The singer’s all-denim dress has since become one of her most infamous red-carpet looks.
She then went with a revealing lace minidress for her arrival to the 2001 MTV Video Music Awards in September.
This photo was taken moments before Spears hit the stage for one of her most memorable performances.
The outfit for her September VMA performance delivered her most iconic accessory: Banana, the Burmese python.
The emerald green top and jeweled shorts went perfectly with her jungle-themed performance of “I’m a Slave 4 U.”
The 20-year-old returned to her glamorous side with this chic red gown for the Grammys in February 2002.
She paired the elegant look with some seriously voluminous curls.
Spears looked like a movie star in this sparkly silver dress for the London premiere of “Crossroads” in March 2002.
The movie may not have been a hit with critics, but her red-carpet look certainly impressed.
She wore a leather minidress and matching hat for her brief appearance at the 2002 MTV Video Music Awards in August.
Spears was there to present Michael Jackson with an award.
In February 2003, shortly after the singer turned 21, we began to see her more casual side thanks to an influx of paparazzi photos.
Spears was a fan of the velour tracksuit trend of the early 2000s.
She then embraced her status as a regular tabloid fixture in June 2003 with this shirt featuring the Page Six logo.
She kept it relatively simple with this black and white ensemble.
She then opened the 2003 MTV Video Music Awards in August wearing a short wedding dress for a performance with Madonna, Christina Aguilera, and Missy Elliot.
She made plenty of headlines after locking lips with Madonna during the performance.
Spears then took it back to her bubblegum roots with this light-pink top and loose-fitting jeans in November 2003.
She wore the casual look while receiving a star on the Hollywood Walk of Fame.
At 22, Spears wore a gold, beaded dress for the 2004 French NRJ Music Awards in January. It’s one of her most sophisticated red-carpet looks yet.
She paired the dress with some simple matching heels.
The 23-year-old embraced the lace trend of the early 2000s while attending the 2004 Billboard Music Awards in December.
She once again kept the heels fairly simple.
We got the first taste of her maternity style back in July 2005, when she kept it casual on the “Charlie and the Chocolate Factory” red carpet.
Her light-blue tank top said “I have the Golden Ticket,” with an arrow pointing to her belly.
A year later in August 2006, when she was 24, Spears showed off her pregnant glow again with a halter dress and long dark locks.
Spears was pregnant with her second child.
The following year in September 2007, the 25-year-old opened the MTV Video Music Awards in this controversial studded two-piece.
Her performance of “Gimme More” became infamous for all the wrong reasons – many thought the outfit was unflattering and that Spears wasn’t on top of her game.
A year later in September 2008, 26-year-old Spears looked as radiant as ever in this silver Atelier Versace dress.
Many people considered this the official beginning of her comeback.
The 27-year-old arrived at the 2009 Teen Choice Awards in August wearing a classic little black dress.
The dress had some slight sparkle and an asymmetrical strap over the shoulder.
The singer then opted for a black leotard with a sheer overlay for the 52nd Annual Grammy awards in January 2010 at age 28.
Spears paired it with some studded heels and also ditched her signature blonde locks for a lovely shade of dark brown.
The 29-year-old then hit the 2011 MTV Video Music Awards in August, this time in a black sequined playsuit paired with a small belt.
Spears was there to accept the Michael Jackson Video Vanguard award.
At 30, Spears gave us one of her most sophisticated looks with this sequined dove-grey Halston dress in October 2012.
She paired the dress with some jewellery from Alexis Bittar.
She looked stunning at age 31 in this shimmering Michael Cinco Couture dress in February 2013.
She once again traded her signature blonde hair for brunette.
Spears then brightened things up in July 2013 with this sky-blue Herve Leger bandage dress.
She paired the dress with a simple pair of black pumps.
Spears wore a cream-coloured Mikael D Collection dress with floral embellishments in early January 2014.
People drew several comparisons to her outfit from the 2000 MTV Video Music Awards.
She ditched her typical dresses for this vibrant orange jumpsuit with a plunging neckline in September 2014.
As usual, Spears let the outfit be the star of the show, and kept the accessories to a minimum.
The singer went for this skintight sequined dress by Labourjoisie for the 2015 MTV Video Music Awards in August at age 33.
The dress featured a cut-out design around her midriff.
It was back to black for the 34-year-old’s arrival to the 2016 Billboard Music Awards in May with an outfit that looked similar to her previous sheer ensembles.
The flowing train and thigh-high cage heels helped elevate the look.
The singer then wore this sheer crystal-embellished dress by Uel Camilo in February 2017.
She paired the dress with some subtle strappy heels.
For the 29th Annual GLAAD Media Awards in April 2018, Spears went with a sparkly minidress by Giannina Azar.
Spears paired the look with Christian Louboutin pumps. The singer was presented with the Vanguard Award for her support of the LGBT community.
In October 2018, Spears announced her second Las Vegas residency called “Domination” while wearing a little black dress.
The $US1,520 design from Death by Dolls features star-shaped cutouts on the sides and metallic fringe detailing.
Spears wore a red dress as she walked the red carpet with her boyfriend Sam Asghari in July 2019.
Spears and her boyfriend made their red carpet debut as a couple at the premiere for Quentin Tarantino’s film “Once Upon a Time in Hollywood.”
The pop icon sported a red dress by Australian label Nookie, which she paired with black platform heels and a diamond choker.
Spears went with a strappy dress as the couple hit the red carpet together for the 2019 Daytime Beauty Awards in September.
Spears showed off her new brunette locks as she came out in support of Asghari, who received the outstanding achievement in fitness award at the event.
The singer sported a classic little black dress, and was back in black platform heels.
- Read more:
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- Britney Spears’ ex-husband Kevin Federline is reportedly receiving 70% custody of the couple’s children in new agreement
- The 19 best performances at the MTV VMAs ever, ranked
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