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Britney Spears' 10 most iconic outfits

The Toxic singer has had more than a few memorable fashion moments…

Britney Spears holding a snake
Orin Carlin
Content Writer
23 October 2023
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Britney Spears is a woman of many talents. A bona fide hitmaker and pop culture legend, she is also a fashion icon, and has the archive to prove it. 

Coinciding with the release of her memoir, The Woman in Me, we've dipped into Britney's fashion history to revisit some of her most memorable looks.

 Her music video 'fits speak for themselves – from glossy red catsuits to air hostess mini dresses, Britney covered a lot of ground, using fashion to make a lasting impact on her audience.   

But there's more where that came from - the star always brought her style A-game, be it on stage or the red carpet. Get ready for an influx of Y2K nostalgia

READ: The most stylish celebrity Halloween costumes of 2023

Hello! Fashion shares Britney Spears' most iconic outfits:

Pretty in Pink  

Britney Spears wearing sequin disc trousers © Getty
1999 Teen Choice Awards

A fresh-faced Britney brought the glam in sequin disc trousers and a classic tank top ahead of her win for the Single of the Year award with Baby One More Time.

 The Boob Tube Moment

Britney Spears wearing a boob tube © Getty
1999 Baby One More Time tour

Giving major Baby Spice vibes, Britney rocked a glossy pink boob tube while performing on tour. The jewel in the crown? Matching knee patches. Future fashion icon behaviour, if ever we saw it.

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Fedora Fun

Britney Spears wearing an orange and pink tie-dye dress© Getty
2000 Billboard Music Awards

The Oops!... I Did It Again singer went for a seriously jaunty accessory, demonstrating her fondness for the unconventional fedora. The star teamed her hat with a vibrant tie-dye dress and a glitzy choker. If anyone can pull it off, it's Britney…

Futuristic Glam

Britney Spears wearing a silver jacket © Getty
2000 Oops!... I Did It Again tour

Britney went hard on the metallics for a show at Wembley Arena, sporting a silver chainmail-leather one-shoulder jacket and bedazzled jeans.

 Hollywood glam meets Y2K

Britney Spears wearing a white dress and stole © Getty
2000 Grammy Awards

The star oozed Old Hollywood glamour at the Grammys at the turn of the millennium in a white cut-out gown with a fluffy stole.

 Super low-rise

Britney Spears wearing corset and low-rise trousers © Getty
2001 N'SYNC Celebrity album release party

Braving a seriously low-rise waistband, Britney exuded Y2K glam, teaming her tiered ruffle trousers with a distressed corset and a blingy choker.

 Double Denim

Britney Spears and Justin Timberlake wearing double denim© Getty
2001 Annual American Music Awards

Britney and then-boyfriend Justin Timberlake can't possibly have predicted how iconic this matching denim moment would become, providing fashion fanatics with couple's costume inspiration for years to come.

 The Literal Boa

Britney Spears holding a snake © Getty
2001 MTV Video Music Awards

Britney took her performance to the next level in 2001 when she shared the stage with an albino python, recently recalling on Instagram how "scared" she felt when she was handed the reptile. Hardly surprising. Now that's true dedication.

 Pastel Perfection

Britney Spears wearing a pastel dress over jeans © Getty
2002 Crossroads premiere

The baker boy cap. The asymmetric ruching. The turned-up jeans. The skin-tight boots. So much to unpack here, but somehow Britney makes it work. Don't ask how. 

Crystal Extravaganza

Britney Spears wearing a sheer crystal mini dress© Getty
2017 Pre-Grammy Gala

The star wore a sheer mini dress in 2017, adorned with clusters of celestial embellishment over a sheer mesh, richly reminiscent of her iconic Toxic bodystocking.

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