The Best Britney Spears Style Moments of All Time

Complete with all the low-rise jeans and baby tees a girl could dream of.

Did anyone define the 2000s more than Britney Spears? Between her classic songs and show-stopping performances to famous pop-culture moments, it’s not an exaggeration to say that no one has influenced the entertainment industry quite like her. And, with over 20 years in the industry under her (super-low-rise) belt, the superstar’s legendary career has also gifted us with some majorly memorable Britney Spears style moments along the way.

It’s not unusual for Spears to make headlines but, with the upcoming release of her new memoir, “The Woman In Me” just around the corner, the singer has been in the news a lot lately — and for good reason.

After years of forced silence due to her previous conservatorship, the superstar is taking back her voice with her new book. The highly-anticipated memoir has already shared several shocking revelations, including details on Spears’ relationship with ex-boyfriend Justin Timberlake as well as previously untold tales about her short-lived romance with Colin Farrell.

Beyond the juicy gossip, the memoir has reminded us of how far Spears has come, how much she’s accomplished throughout her truly *iconic* career, and, of course, all her best style moments along the way.

So, without any further ado, please allow us to lead you on a trip down memory lane as we present the most memorable looks from the amazing career of Ms. Britney Spears so far.

“…Baby One More Time” Inspired

For one of her early performances in 1999, a young Spears sported a shimmery hot pink strapless crop top, white low-rise cargo pants and matching pink knee pads. Consider it a homage to the singer’s famous look from the “…Baby One More Time” music video, which premiered just a few months before this performance. Pure pop perfection!

Old Hollywood Glamour

For the 42nd Annual Grammy Awards in 2000, Spears wore an all-white ensemble featuring a simple yet oh-so-sophisticated gown by Randolph Duke with eye-catching strap cutouts and a small train. To make the look even more fabulous, the singer paired the dress with a matching fur stole by Oscar de la Renta, a diamond necklace and an elegant makeup look. So simple but so good!

The Iconic “Slave 4 U” Performance

A round-up of Brit’s best style moments just wouldn’t be complete without including this legendary “Slave 4 U” performance outfit from the 2001 MTV VMAs.

In a clear attempt to begin distancing herself from her “teenage pop star” image, Spears wore a green bralette and super low-rise blue shorts, which were artfully embellished with jewels and scarves that swayed alongside her killer choreography. And of course, everyone will remember the yellow Burmese python she wrapped around her shoulders, an experience that she recently recalled as “even more terrifying than it appeared.” Talk about commitment!

On the “Crossroads” Red Carpet

Britney Spears’ style for the wholesome coming-of-age film Crossroads was just so 2002.

Brit looked pretty in pink as she wore a ruched light pink dress over a pair of blue skinny jeans. Taking the rose theme even further, she accessorized with a matching leather hat and finished it off with sky-high stiletto boots.

Donatella’s Muse

In 2002, Spears and Donatella Versace proved that they were a match made in style heaven.

For Versace’s runway show, Brit wore a sparkly, semi-sheer multicolour gown designed by Donatella herself. Years later, Donatella proved that the duo are still close as she shared a heartwarming congratulations message to the star when she was freed from her conservatorship in 2021. So sweet!

The Baby Tee

With a Starbucks in hand, Spears had just one message as she roamed the streets of London — and she let her outfit do all the talking.

In a look that, allegedly, came just after her split from Justin Timberlake, Brit helped birth the baby tee trend as she sported a tiny shirt adorned with two words, “dump him.” To complete the casual outfit, the singer wore low-rise sweatpants, a fur-trimmed coat and a navy suede cap with her hair styled in pigtails. You could argue that this look breaks a lot of conventional “fashion rules” yet, somehow, it all just works.

A Cheeky 2003 Performance Look

For a live Times Square performance on MTV’s TRL back in 2003, Brit chose the lowest-rise pair of pants we think we’ve ever seen.

The brown leather trousers not only showed off her ultra-toned lower torso but also revealed Spears’ purple thong as a cheeky addition to the outfit. Beyond Brit’s killer abs, the look featured a cropped, “ripped” top adorned with blue flowers and a grey fedora with a matching floral accent. Talk about a show-stopping look!

Juicy Tracksuit

Brit surely didn’t know it at the time, but this off-duty look would serve as major fashion inspo for years to come.

As she strolled around Hollywood with her trademark blonde hair in a super-cute messy updo, while sporting very 2000s-esque shades and a blue head-to-toe velour Juicy Couture sweatsuit, Britney Spears cemented her style in every ‘it’ girls memory for years to come.

Sparkling at the 2008 VMAs

After taking home three of the biggest awards of the night, Spears was all smiles at the 2008 MTV VMAs.

As she posed with her new trophies, Brit stunned in a sparkly and sequin-adorned dress that would surely fit right in with today’s ultra-popular silver clothing trend.

An Edgy 2016 VMA Look

Brit returned to the VMAs in 2016 with a stellar, high-energy performance, but before that, she walked the red carpet and showcased the quintessential Britney Spears style.

Complete with her long, layered blonde hair, Spears stunned in a cutout black dress with matching pumps, proving that even 15 years after her iconic “Slave 4 U” performance, she was (and still is) a style force to be reckoned with.