A Timeline Of Britney Spears' Most 2000s Outfits We All Forgot About (& Really Shouldn't)

No one can deny it. Britney is simply da bomb! From the moment she exploded onto the music industry in the late '90s, Britney Spears has managed to turn heads on stage, on the red carpet, on social media, and in tabloids!

It didn’t matter if she was all gussied up for an awards show or if she was out and about on her way to Starbucks. Whatever Britney wore, it instantly became the talk of the town. The media was a bit more obsessed with her lifestyle and her quirky little outfits than with her catchy songs.

But Britney seems to be cooling her heels these days. So, fans will have to wait and see if she'll eventually snap out of it and go back to wowing them with her insane outfit choices. But as long as she's on her hiatus, let’s take a look at some of the interesting fashion choices she’s made throughout the 2000s.

Some of these iconic pieces literally defined an era. Whether Britney was rocking a "matchy matchy" velour tracksuit or extremely low rise jeans paired with an NFL cheerleader top, she always managed to look on point.

Let’s take a trip down memory lane to see some of the most bizarre outfits our beloved pop diva has worn over the years. We’re pretty sure we’ll never forget these iconic and controversial fashion choices anytime soon.

20 This All-White Bejeweled Ensemble And Purple Eyeshadow At The Teen Choice Awards

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There are fashion looks out there that only Britney herself could pull off, but the line between the late '90s and the 2000s is definitely blurry.

Crop tops, bandanas, bedazzled tops, velour pants, and everything baggy was all the rage back then.

But this little number kinda looked like someone on her style team grabbed an arts and crafts tool and a couple of beaded jewels, and glued them all over a white crop top. But hey, it still looks spectacular! There's a certain simplicity about Britney's style in the late '90s/early 2000s. But that would soon be a thing of the past because she was just getting started!

19 Back When A Scrunchie And A Double Layered Top Was All That


Talk about a major '90s throwback! Britney looked like a high school cheerleader with the double layered blue and white top and a totally adorbs scrunchie on her hair. But Brit Brit was starting to define her look slowly, and soon enough, crop tops became part of her brand. That was one gal who wasn't afraid of showing off her belly button, that's for sure!  She must have knocked everyone’s socks off when she attended the 3rd Annual Zootopia Charity Concert hosted by Z100 at the Continental Airlines Area in New Jersey. Back in the day, Britney claimed she wasn’t “that innocent,” and judging by her edgy looks, the whole world was starting to believe her!

18 Britney's Choice Of Pants For The Teen Choice Awards Defined A Whole Era, Really

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The '90s were almost over, but Britney’s stardom was just about to take off. So, at the Teen Choice Awards, she wore these flared sequined pants that genuinely defined the 2000s. Girly, shiny, bold, and cutesy was the way to go!

That night, Britney performed, presented and won, something that would end up happening a LOT for the talented gal from Louisiana.

The Teen Choice Awards picked her to introduce the show, and it was all thanks to the fact that “Baby, One More Time” was such a hit. Perhaps you wouldn't have been able to wear these pants to school, but you probably wished you could've worn them to the mall and make heads turn.

17 Brit Attended The Pre-Grammys Party With A Mesh Top And Some Teenybopper Pants

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By the new millennium, Britney shined bright like a diamond. She dropped it like it was on fire in this glitzy mesh top and teenybopper pants with some fur in the bottom. Now, stylists might look back at this ensemble and think, "wow, that was a bit of a mess," but then again, Britney was always a bit of a beautiful mess! She needed to make a splash and stand out from everyone out there, and with risky bold outfits like this one, it wasn't hard to do. We wish Britney would pop up in 2000s gear more often nowadays, but we know she's too busy rocking her Vegas residency and raising her kids. Still, we certainly wouldn’t mind seeing this outfit make a comeback!

16 A Little Galactic Outfit For Her "Oops... I Did It Again World Tour"


The goddess of pop (and pretty much everything) looked like she had been dressed by a fashion designer from outer space on her "Oops... I Did It Again" tour. Aliens must've stumbled into Britney when she was filming her music video, which was set on Mars, and gave her a few pointers because the look was an extravagant galactic little number.

But the entire Y2K era inspired other pop artists to don similar styles.

Everyone from Jennifer Lopez, Will Smith, TLC, and Sisqo were rocking some type of silver and white "futuristic" outfit. Nothing happened in the end, but at least we were left with some amazing pop videos. But hey! We're 100% down with the Y2K futuristic trend making a comeback. It was definitely a wild ride!

15 Britney's Purple Ensemble Kind Of Looks Like An Ode To Prince's "Purple Rain"

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Britney wore this purple ensemble to the opening of Planet Hollywood in London and let’s just say that it looks like she was playing a tribute to Prince’s “Purple Rain.” She even looked a tad nervous to be stepping out on something that looks a teeny bit "costumey."  The way she’s yanking on her top makes you wonder if the shirt ripped open or if she'd put it on backward. But hey! Back when these photos started making the rounds in Seventeen magazine (and pretty much everywhere), we didn't see anything wrong with it! In fact, we would've spent an entire year's allowance on this flashy Britney outfit. And as matter of fact, we would still pay real good money to own those pants. Ugh!

14 Cropped Jerseys And Bejeweled Belly Buttons Went Really Well Together, According To Britney

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At this point, Britney had mastered the art of turning heads. She could've worn a potato sack and a string and she still would've made headlines.

There was something so alluring about her cutesy popstar outfits that fans all over the world couldn't wait to spot her out and about. 

But even when she was meant to make an appearance on TV, the girl still managed to look bomb, like that one time she paired her gorgeous bejeweled belly button with a football jersey style shirt and low rise jeans. Sure, the look was pretty casual for Brit Brit! But she still dazzled everyone when she was invited to appear on TRL to promote “Oops!... I Did It Again.”

13 Denim While Dating *NSync's Justin Timberlake. Life Goals!


In the early 2000s, back when Jessica Biel wasn’t on Justin Timberlake’s radar yet, Britney Spears stole the NSync hunk’s heart. Look how cute they are holding hands as they head to the VMA after party! These two seemed destined for one another, and even though they’re not together anymore, we can look back to a time when these two were totally “NSync” with one another. But Britney was the one in the spotlight; finally, she was starting to realize that denim was the way to go. Her half denim jacket and her bellbottom jean pants were such a hit that she wore them on the set of her "Overprotected" video. Whatever the case may be, we would've kept them too, Britney! These are just awesome!

12 Brit Absolutely Loved Girly Girl Outfits Like This Pink Lace Little Number


In the 2000s era, everything was so exciting for Britney fans. She made everyone's jaws drop to the floor when she performed her hit song, “I'm a Slave 4 U” while wearing a python around her neck. Then there was that iconic moment between her and Madonna when they were both live on stage (who could forget?).

And yet, fame was still pretty new to Britney, so she really wanted to put herself out there.

She knew that her uber sweet outfits wouldn’t cut it, so she eventually moved on to some “super out there” pieces to define her style. But we still loved some of her more retro girly girl outfits like this one, where she looked as sweet as pie!

11 Back When Coordinated Couples Outfits Was A Thing!

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Ask any Britney fan, and they’ll probably tell you that this was possibly their number one favorite look. While she was still dating Justin Timberlake, Britney decided to stick with the denim look and wore a denim dress fit for a princess. She also had a matching denim bag that was full of glittery bling that was... well, blinding! But not as much as JT's matching denim outfit! For some strange reason, Timberlake looked absolutely great as a denim cowboy popstar. Their coordinated couples outfit could've ended up looking like a costume, but when these two showed up in matching outfits, the moment became instantly iconic. We’re pretty sure the pair managed to boost the sales price on denim clothing that year!

10 Britney Made Quite A Splash At Her "Britney" Album Release Party With This Furry Coat!


In 2001, Britney rocked this retro look at the "Britney Spears" Album Release Party at Centro-Fly in New York City. There aren’t a lot of folks who could put on a furry coat like this one and still look stunning. But Britney could do no wrong.

She looked amazing in a soft ocher furry coat, which probably kept her warm during the chilly weather back in November of that year.

Brit Brit must've felt all cozy and warm, because she still managed to don a pink dress under it, in case she got too warm once she got inside. And as her albums continued to take off, so did her fashion sense.

9 Britney Performed "Stronger" With The Kind Of Energy That Gave Us Shivers


Now this is the kind of look you see someone like Jennifer Lopez wearing on stage these days. But it is thanks in part to groundbreaking stars like Britney, who wore the most amazing outfits all throughout the 2000s era. And if you watched this performance, you know she blew everyone away with this one! She was still at the peak of her fame and a force to be reckoned with. Seriously, if there's a performance that proves she's the one and only Queen of pop, it's this one! Britney broke into a choreography routine right in the middle of her song “Stronger.” And she danced with so much energy, it's kind of giving us some nostalgic vibes. Plus, she did it all in low-rise jeans!

8 Everything About The Premiere Of Crossroads Was So 2000s


While attending the LA Crossroads premiere in 2002, Britney took color coordination to the next level. She sported a pale pink hat, a ruffled dress, and some knee-high boots. But that’s not all! She also had on some fitted jeans and a series of choker necklaces.

But this was a huge deal for Britney: she wasn’t just rooting for the film because she liked it, she was promoting it because she was in it.

The movie is about three childhood friends and a guy they meet along the way. The friends take a road trip that cements their bond and allows them to find themselves. That’s seriously so Britney!

7 Brit Brit Couldn't Choose Between A Sheer Sarong Or A Low Rise Pair Of Jeans

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Britney was in quite a pickle in 2002. She couldn’t decide between a translucent sarong or a low-rise pair of jeans. Then she realized, she’s Britney! She can wear whatever she wants, right? So rather than flipping a coin and trying to pick, she decided to wear both to the Crossroads Press Junket. Most people would be too afraid to wear something that looks like a tablecloth over a pair of jeans. But Britney made the look so fashionable that some of us probably wondered why this wasn’t a thing before Britney wore it. Seriously, can we make this a thing?

6 Britney Showed Up With This Black Biker Leather Ensemble

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It’s one thing to see her wearing a quirky denim dress or a girly girl pink outfit and fur coat, and a completely different thing to go full on leather. But then, look who we’re talking about!

Everyone was picking their jaws off the floor after Britney showed up in a black biker leather outfit that was a far cry from her usual cutesy popstar outfits.

But maybe this was her way of letting everyone know that behind the Mickey Mouse Club "good girl" exterior was a confident young woman waiting to come to the surface. Only Britney could make a leather cap, lace gloves, and lace-up shoes look cool!

5 Britney Started Off The Year By Wearing This Iconic Juicy Couture Velour Tracksuit


This might look like something you’d see the Real Housewives in, but this Juicy Couture velour sweat tracksuit was worn by none other than our very own pop princess. By this point, she and Timberlake were dunzo, and he had already released “Cry Me A River,” which was basically a diss track. So, we honestly can’t blame the pop diva for sporting leisurewear while she was out and about. She was still reeling from the breakup! And this was probably comfortable and therapeutic as her heart mended in time for her next potential heartbreaking relationship. We personally love post-breakup Britney outfits!

4 She Was Advertising Perez Hilton's Blog From Back In The Day


In 2003, Britney decided that fedoras were cool again. So she stepped onto the red carpet with one and, bam! They were an instant hit. But that wasn’t the most impressive part of her look. She wore on a ripped crop top, a diamond belly-button ring, and a mini-skirt that put a whole new meaning to the term hip huggers.

Ironically, Perez Hilton’s blog was named Page Six, so we’re assuming that the Six, Six, Six on her top was designed to avoid issues.

But most people were probably too busy gawking at her printed Patricia Field leggings to notice the similarity in the cropped top’s name.

3 Britney's Surely "Got That Boom Boom" And A Pretty Sassy Outfit At TRL

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Once again, Brit Brit decided to put a fedora on as she performed on TRL’s Brand Spanking New. She also wore a crop-top that looked like it had run into a tiger’s claw and lost. We’re sure this drew plenty of attention. The pop star also showed her pride in her amazing abs by baring them again, making this a regular thing at this point. The overall look is a combination of stretched fringe and “pleather,” but she obviously “Got That Boom Boom” going while she was on stage, performing a song by the same name. By this point, Britney fans knew this gal was going places.

2 No One Expected To See Her In This Bubblegum Pop Little Number

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In November 2003, Britney was given the honor that most celebs only dream of getting from the moment they head to Hollywood. She received a star on the Hollywood Walk of Fame. So, what did our pop diva wear on for this momentous occasion? Was it a top full of bedazzling beaded jewelry? No.

Spears decided to embrace her love for pink once again and wore a pink top under a furry looking pink coat and a pair of loose-fitting bellbottom jeans.

Just when you thought Britney had locked in the bad girl look, she went off and did this. We just loooooved how unpredictable she was!

1 Britney Glammed It Up At The NRJ Awards


By 2004, Britney had figured out how to mix classy and modern and make the front cover of every magazine out there. She looked ravishing in this dress that seems like something you’d expect to see in a dance competition. If you had asked what we thought about this look back in the day, we would have given Britney an A+ all around. Sure, it was a little showgirl-ish but it totally went with her whole style. We’d have to say she did a mighty fine job when she chose this stunning ensemble for the NRJ Music Awards. Now can anyone bring these outfits back? We're dying for 2000s fashion to make a comeback. It's about time, don't you agree?

Sources: Cosmopolitan, VH1, Bustle, Popsugar, Harper's Bazaar

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