Since 1999, the world has been captivated by a pop princess from Louisiana. From the minute Britney Spears burst onto the scene in one of the most unforgettable music videos (and outfits!) of all time with the release of her debut single …Baby One More Time, the chart-topper has held a special place in people's hearts that no other star has come close to emulating.
Over the decades, as her fans grew up, so did Spears. But all these years later, she's never lost the sense of fun that always stuns with her fashion choices. From her early days in the spotlight as the quintessential influencer when it came to Y2K trends (think: embellishment, low-rise denim, butterfly details, and crop tops galore) to denim on the red carpet, her style has led to some of the most memorable looks of the entire era.
While the history-making performer has had her ups and downs in the spotlight, her beauty, poise, style, and resilience have ensured she's remained at the forefront of pop culture and entertainment—and on mood boards.
Read on for some of Spears's best looks on and off the red carpet.
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'Once Upon A Time in Hollywood' Premiere, 2019Getty Images
At the premiere of Once Upon A Time In Hollywood, Spears looked radiant in red with a signature body-con dress and black platforms. The asymmetrical neckline offered a twist to the otherwise classic silhouette.
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GLAAD Awards, 2018Getty Images
While being honored with the Vanguard Award at the GLAAD Awards in recognition of her commitment to fostering diversity and acceptance and championing those in the LGBTQIA community, Spears proved her icon status in a beaded fringe mini by Giannina Azar and sky-high Louboutins.
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In Paris, 2018Getty Images
Britney goes boho! Spotted out and about on the streets of Paris, the singer went for a more bohemian and eclectic look in a ruched chiffon top and suede slouchy boots, anchored by her favorite low-rise denim. Old habits die hard!
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Pre-Grammys Party, 2017Getty Images
Spears truly loves a sparkly statement. At Clive Davis' annual pre-Grammy celebration, Spears opted for a sheer sequin dress by Italian brand Uel Camilo.
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MTV VMAs, 2016Getty Images
Spears looked sensational when she rocked a black asymmetrical and cut-out slinky zip-up dress by Julien Macdonald at the MTV VMAs in 2016.
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St Bernard Project Event, 2011Getty Images
Spears embraced a dominant trend of 2011—neon bandage dresses!—in a form-fitting number by Herve Leger by Max Azria while hosting a charity event in aid of the Southern Style St Bernard Project in Beverly Hills.
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Grammy Awards, 2010Getty Images
Brunette Britney! The performer showcased her new look when she rocked up to the Grammys in 2010 in fishnet stockings and a little black sheer dress for the occasion.
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MTV VMAs, 2008Getty Images
Our girl went home victorious after the MTV VMAs in 2008, where she bagged three Moonman accolades on the night—all while looking resplendent in custom Versace.
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'Charlie & the Chocolate Factory' Premiere, 2005Getty Images
When expecting her first son, Sean, in 2005, Spears infamously wore this baby blue tank top to the Los Angeles premiere of Charlie and the Chocolate Factory.
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In Arizona, 2005Getty Images
Ever the trendsetter, Britney Spears wore a babydoll dress and Uggs, so a generation of her followers wore a babydoll dress and Uggs.
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Versace show, 2003Getty Images
Eagle-eyed fans will know that when Blake Lively arrived at the NYC premiere of It Ends With Us, her scene-stealing vintage Versace frock was the very same one once worn by a young Spears at the luxury label's 2003 runway show in Milan.
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At New York Fashion Week, 2003Getty Images
Back in the day, Spears lent her star power to the front row during NYFW. In 2003, she caused a paparazzi storm at 'The Tents' in Bryant Park when she showed up to support the Dieselstylelab Spring Summer 2004 collection.
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'Crossroads' Premiere, 2002Getty Images
She's not a girl not yet a woman… but she's certainly red carpet royalty. The year 2002 saw 20-year-old Spears promoting her first feature film, Crossroads, across the globe. The promotional run led to no shortage of looks, so it's hard to pick a favorite, but it might just be this blinged-out sparkly dress from Julien Macdonald's fall 2002 collection for the London premiere that takes the top prize for us.
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American Music Awards, 2001Getty Images
Spears took a big risk by wearing denim to a red carpet. But it worked so well, it has become an iconic moment in pop culture. Spears later said, "I get that it was tacky—but it was pretty great in its own way, and I'm also happy to see it parodied as a Halloween costume."
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MTV VMAs, 2001Getty Images
Her turn at the VMAs in 2001 will forever be associated with that live performance of I'm A Slave 4 U (yellow python and all). But her red carpet arrival in a navy lace mini by Dolce & Gabbana is equally as important in our books.
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In Paris, 2000Getty Images
Admit it—you begged your parents to let you get your belly button pierced in 2000 after seeing this image of the star at the Eiffel Tower in bootleg jeans, platform sandals, and an ombré cropped wrap top.
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Grammy Awards, 2000Getty Images
A fresh-faced Spears cemented her status as a star to watch when she graced the red carpet at the Grammys in 2000 (where she was a first-time nominee and also performed at the ceremony) in a white Randolph Duke gown, Oscar de la Renta stole, and glittering diamonds. Old Hollywood glam meets Y2K.
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MTV VMAs, 1999Getty Images
The all-American teen from the South made sure people sat up and took notice when she made her debut at the VMAs in 1999, thanks to a daring look involving very '90s low-slung shimmering python-printed pants and a metallic cropped jacket and top.
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