The Most Iconic Britney Spears Outfits of All Time

So many fedoras, so little time!

britney spears outfits
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Britney Spears has given us gems such as "Oops I Did It Again" and "Lucky," the song that was responsible for a lot of scream-singing in my childhood bedroom. And let us not forget her historic (to me) Hollywood movie, Crossroads. I mean, we have Britney to thank for a lot of amazing stuff. But with all of her artistry, sometimes her iconique fashion moments aren't the hottest topic of discussion when bringing up Brit. That might need to change. Britney has given us outfits of glamour and some more casual, chic looks. Her range is impeccable. Yes, I'm referring to her vocals, but ALSO the outfits. For someone who’s been in the spotlight as long as Britney Spears has, there’s bound to be a LOT of nostalgia-inducing ensembles. Ahead, a look back at Brit’s most iconic outfits of all time. And, yes, Justin Timberlake does make some minor appearances. You're welcome.

britney spears in concert
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This Matching Tube Top/Knee Pad Combo

Immediately Googles "white pants with built-in knee pads." Sorry not sorry, I'm obsessed.

southern style st bernard project event with ambassador britney spears
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Neon Bodycon Dress

Brit is glowing! Maybe it's the bright bodycon dress or her radiant smile. Whatever it is, she's rockin' the look.

britney spears
Dave BenettGetty Images
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All Embellish Everying

This photo was snapped at a Crossroads press event can tell. The low-rise denim with the sheer wrap on top is a) gorgeous and b) a sign of the times.

44th annual grammy awards
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Red Hot Grammy's Red Carpet Look

"That's why her hair's so big. It's full of secrets."

the 42nd annual grammy awards
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White Gown + Floofy Shawl


britney spears sighting in los angeles   june 22, 2009
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The Early Aughts Called

Just sink into this outfit and let it take you back. The french manicure, the huge boho bag, and the oversized round sunglasses create the ultimate early-2000's vibe.

21st annual elton john aids foundation academy awards viewing party   arrivals
Maury PhillipsGetty Images
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Stunning and Sparkly

Photos of brunette Britney are few and far between, but j'adore this one of her with a stunning dark and sparkly gown to match her equally dark do.

britney spears presents her dessous collection 'the intimate collection'
Sascha SteinbachGetty Images
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Office Barbie

Okaaaaay Ms. Britney showing us up with some white party realness. And that lil' bob?! Trés cute.

2016 mtv video music awards   arrivals
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Sexy! Cutouts!

There's a lot of skin happening here and I...don't hate it.

london celebrity sightings    september 28, 2016
Neil MockfordGetty Images
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Incognito Chic

I'll give it to her, Brit sure knows how to slay the accessories game. Matching her hat, sunglasses, jacket, and over-the-knee boots, she's bringing some chic AF vibes to her wardrobe.

ama '98
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Your Junior High Dream Dress

A sheer slip dress? Check. A bejeweled headband? Check. Extra-strappy heels? Check.

britney spears in hoodie and bucket hat
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Casual Britney FTW

Bucket hat Britney was peak Britney, IMO.

britney spears
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No Shoes, No Problem

Here, Brit poses in a closet (casual) in a striped tank and baggy jeans. Looks like she has no shortage of sneakers, though!

britney spears photo by steve granitzwireimage
Steve GranitzGetty Images
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Pretty in Pink

Here’s Britney at the very first Teen Choice Awards. And there are big sequin paillettes on her pants, which take her 'fit to a whole new level.

britney spears
Time & Life PicturesGetty Images
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Texture, Texture, Texture

There is just so much going on here, but perhaps best of all is the frosted eyeshadow? Okay, or the marabou-feather hemline on Brit’s silk pants. I just can’t decide!

Britney Spears arriving for the 1999 MTV Music Video Awards in NYC 09/10/99.
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This Sheer Top!

More dramatic eyeshadow circa the 1999 MTV Video Music Awards. Also, there are more marabou feathers on the sleeves of this epic see-through top.

britney spears
Ron GalellaGetty Images
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This Metallic Lewk

TBQH, it’s like Britney and Melissa Joan Hart (remember, Brit and Melissa both starred in the “(You Drive Me) Crazy” music video alongside Adrian Grenier) had a competition to see who could look more ’90s. They both win!

mtv europe music awards ceremony in dublin, eire   1999, britney spears at the european mtv music awards in dublin, ireland at the european mtv music awards in dublin, ireland photo by brian rasicgetty images
Brian RasicGetty Images
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Black Is the New Black

Belly chains and skirts over pants! You love to see it.

britney spears
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Hot Pink Lace

Surprisingly, her square-toe aqua shoes are VERY much in right now. Who would have guessed the trend would make a comeback?

britney spears paris
Dave HoganGetty Images
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Le Crop Top

Just a cute photo of Brit in a crop top and platforms in front of the Eiffel Tower. So fashun.

britney spears photo by james devaneywireimage
James DevaneyGetty Images
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Neon Pink Cowboy Hat? Yep!

I have never seen so much going on with an outfit, but wow, do I love it. Britney’s commitment to statement headwear is impressive, y’all.

britney spears
Chris WeeksGetty Images
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Orange and Pink and This Hat

This is iconic and not just because of the hat. It’s Britney at the 2000 Billboard Music Awards, and never has anyone ever dressed better for the red carpet.

ron galella archive   file photos 2010
Ron Galella, Ltd.Getty Images
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Bring Back Patent-Leather Pants!

Here, Britney performs in a lace-up crop top and patent-leather pants with a buckle belt at Dodger Stadium in Los Angeles.

2001 mtv video music awards   show
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A Snake Accessory

Behold: Britney Spears at the 2001 MTV Video Music Awards. The look of the century!

no tabloids    britney spears and jennifer lopez during 2001 mtv video music awards   audience and backstage at the the metropolitan opera house at lincoln center in new york city, new york  photo by kevin mazurwireimage
KMazurGetty Images
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Sophisticated Lace

Look, she’s even serving hats by osmosis! Any excuse for a good J.Lo photo; this is from the 2001 MTV Video Music Awards, but it could just as easily be from last year's.

britney spears photo by kmazurwireimage
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I Heart This Look

And when she’s not wearing hats, she’s rocking bandannas, like this yellow one tied around her short hair, with an “I Love Punk” shirt, distressed jeans, and colored sunglasses.

375090 39 pop star britney spears, winner of choice female artist attends, august 6, 2000, at the 2000 teen choice awards in santa monica, ca photo by chris weeksliaison
Chris WeeksGetty Images
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Pink Fringe Is V Surf Vibes

Brit picked up a Teen Choice Award in a fringed pink mini and strappy heels. Sidenote: I wonder where people actually store these surfboards?!

no tabloids    britney spears and justin timberlake during the 2000 mtv video music awards at the radio city music hall in new york, ny  photo by kevin mazurwireimage
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Date Night Lewk

This chunky knit turtleneck was a major menswear moment, and Britney’s choker is cute too.

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Statement Tee

Remember when we all wore shirts like this? Although no one can wear a crop top that says “Control Freak” quite like the pop star can, TBH.

exclusive, premium rates apply britney spears and justin timberlake photo by kevin mazurwireimage
KMazurGetty Images
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Starry Print

Justin and Britney are back again, this time in contrasting outfits. Brit went with a classic zip-up dress with stars and metallic details, while JT looked like he just auditioned for The Matrix. What a time.

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