Britney Spears’ Style Evolution — See How Much It’s Changed Since Her Rise To Fame!

Everyone knows Britney Spears is not only the Princess of Pop but also a fashion icon. From her “girl next door” vibe during her teenage years to rocking some seriously sexy ensembles as she grew up, the “Stronger” singer has worn it all.

While Britney still likes to dress up, she frequently ditches glam outfits for some stylish sweats. In September 2019, the “Slave 4 U” crooner announced she was taking a break from work. Since then, she has been dedicating herself to working out even more.

“I hope y’all haven’t forgotten about me!!!” she captioned a series of Instagram photos of herself on stage. “I’m taking this transition in my life to focus on what I really want … I’ve been working nonstop, well, since I was 8 years old in the business. Sometimes it’s good to stop and reflect!!!! Miss you all … I really do have the best fans in the world!!!”

Luckily, Brit not only has support from her fans but also from her boyfriend, Sam Asghari. The personal trainer is on board with the singer’s plan to take some time off.

“That’s a great message,” the model divulged to Entertainment Weekly in October 2019. “The same goes with me. I always take some time away from everything on myself. You gotta do that stuff in order to stay on top of your career, stay on top of your life, so you can have more to offer to your family members and people that you love the most.”

One of the things Britney and her beau bond over the most is their love for working out. In July 2019, the blonde beauty shared some of her fitness tips, and it’s not surprising she’s managed to stay in shape all these years.

“I’ve just gone 15 minutes on the treadmill,” she said in a video via Instagram. “Usually my base workout is 15 minutes on the treadmill, and then, I get off and do stretching yoga, arms, a little pilates. Then, I get back on again and do another 15 minutes. But today my challenge is to go 30. Do you think I can do it?” Of course, she did it. ~ She’s Britney, bitch. ~

Keep scrolling for all of Britney’s most memorable looks throughout the years.

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Britney Spears attending Jingle Ball in December 1998

PRINCESS OF POP

A teenage Britney attended Jingle Ball back in 1998.

Britney Spears at the 26th Annual American Music Awards

ROYALTY

Brown long curls! The princess of pop looked more like a princess than anything else at the 1999 American Music Awards.

Britney Spears wearing blue tank top and grey pants while performing

ON TREND

Remember when cargo pants were a thing?!

90’S GIRL

Not a girl, not yet a woman. The pop star unleashed her sporty side at the US Open in 1999.

DO SOMETHIN’

This is where the grown-up outfits began. Britney wore a revealing, pant romper to the AMAs in 2000.

ROCKING JEWELRY

The trend of the belly button rings began circa, mid 2000.

SLAVE FOR YOU

This is where the princess of pop unleashed her sex appeal onstage for the first time at her 2000 VMAs performance.

COLORFUL

For the 2000 Billboard Music Awards, Britney wore a long orange, robe-inspired dress complimented with a hat.

Britney Spears and Justin Timberlake in denim

NEVER FORGET

This is the iconic look that started the “matching couples” trend: Britney Spears and Justin Timberlake rockin’ denim from head to toe in 2001.

PERFORMANCE OF A LIFETIME

Britney Spears shocked everyone at the 2001 VMAs while performing with a live snake.

Britney Spears wearing a dress and jeans

ALL ACCESSORIZED

For the premiere of her film Crossroads, Britney wore a pink dress, jeans, knee-high boots, and accessorized with a hat. Hmm, only she could pull this off!

CROP TOP QUEEN

Britney rocked a pretty purple crop-top while visiting MTV’s TRL in February 2002.

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CURLY HAIR

For the 2002 Grammys, Brit wore an elegant red dress and large curls.

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TWINNING

Aww, check out these cute outfits Britney and her little sis, Jamie Lynn, wore at the 2002 Teen Choice Awards.

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LEATHER LOOKS

The star wore a cop-inspired leather outfit to the 2002 VMAs before taking the stage.

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THIS TRACKSUIT IS EVERYTHING

Other famous stars, like Kim Kardashian and Paris Hilton, were seen in these: tracksuits!

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ROCK N’ ROLL STYLE

There’s too much going on in this outfit, but hey — when you’re Britney Spears, who cares?

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ICONIC

Alas, probably her most memorable VMAs performance to date: Britney dressed as a bride moments before kissing Madonna on stage.

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NEW HAIR

An uncommon look for the pop star, here’s Britney with a really short ‘do at the 2003 NFL kickoff.

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FUN STYLE

The singer mixed both of her go-to looks: casual and revealing.

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DARK-HAIRED BRITNEY

Brit went back to brown hair for a bit after being a blonde for about six years at this point.

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SHOWING SOME LEG

Once again accessorizing with a boyfriend, Britney arrived to the 2004 Billboard Music Awards with ex Kevin Federline and their dog.

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PREGNANCY STYLE

A pregnant Britney showed off her baby bump at the premiere of Charlie and the Chocolate Factory in 2005.

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SILKY OUTFIT

Britney Spears had even darker hair in 2007.

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SHEER TOP

For a night out, the singer wore black shorts, a see-through top, and accessorized with a grey hat and sunglasses.

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HITTING THE STAGE

After taking some time out of the spotlight, Britney made her comeback performance with “Gimme More” while wearing a sparkly two-piece at the 2007 VMAs.

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IT’S A LOOK

It’s safe to say shades were her thing for nights out back in 2007.

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SPARKLY

For the 2008 VMAs, the pop star rocked an outfit that appeared to resemble another look from earlier in her career.

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PERFORMANCE READY

For her performance of “Womanizer” at the Bambi awards in 2008, Brit embraced a black outfit with a top hat.

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KEEPING IT CASUAL

UGG boots were a big trend in 2009, and Britney gave them a California twist by pairing them with denim shorts and a crop top.

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ALL SMILES

Accompanied by both her sons, Brit wore a fun turquoise dress for the premiere of Smurfs 2 in 2015.

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SLEEK AND STYLISH

Long dresses, like the one she wore here for the 2015 Billboard Music Awards, are a rare look for Britney.

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FUN WITH FASHION

The VMAs is always an experimental event for the pop star and, in 2015, she tried out different colored hair, which gave her a fun, youthful look.

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Britney Spears before the 2016 Billboard music awards

SHOWING OFF HER CURVES

It almost looks like this was inspired by her 2002 VMAs look, except here there’s no hat, but a long cape and train, instead.

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LOOKING CHIC

In September 2018, Britney rocked a sleek, sophisticated little black dress during the announcement of her Las Vegas residency. Get it, girl!

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RED HOT

Britney looked flawless in red at the Once Upon a Time in Hollywood film premiere in July 2019.

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A DAYTIME LBD

Britney wore a sexy little black dress to accompany now-fiancé Sam Asghari to the September 2019 Daytime Beauty Awards in Los Angeles. She also rocked long brunette locks at the time.

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SUMMERTIME

2020 is all about abs for Brit. The fitness enthusiast loves flaunting her toned tummy on Instagram.

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PEASANT TOP PRINCESS

In October 2020, Britney was absolutely glowing in this dreamy crop top and flower crown look.

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SLINKY!

Britney thrilled fans while wearing a backless neon green and black snakeskin print bodysuit in a June 2021 photo, joking in the caption, “I held a snake at the VMAs one time but decided to go ahead 20 years later and become the snake myself!”

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BABY ONE MORE TIME … AGAIN!

Britney gave off some serious fashion vibes from her iconic 1998 “…Baby One More Time” music video in August 2021, wearing a white collared blouse tied just below her bust and exposing her amazing abs.

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RACY RED

Britney wowed in a red slip dress during an October 2021 Instagram selfie video. “I found my pretty little red dress and I felt like I was wearing pajamas but it’s just a slip dress! I doubt I would ever wear this out anywhere but it’s fun to play!” the star wrote in the caption, noting, “I will probably never wear it again!”

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FAIRY PRINCESS BRIDE

Following her engagement to Sam Asghari, Britney donned a pink princess gown in a November 2021 photo. But she revealed to fans, “No … this is not my wedding dress bahahah!!!! Donatella Versace is making my dress as we speak.”