18 Must-See Photos Of Britney Spears In Her Prime

Britney Spears was the hottest thing in the world for a long, long time. If you’d like us to be more specific, Britney Spears was the hottest thing in the world from 1999 – 2006. Her debut album …Baby

Britney Spears was the hottest thing in the world for a long, long time. If you’d like us to be more specific, Britney Spears was the hottest thing in the world from 1999 – 2006. Her debut album …Baby One More Time became the best selling album from any teenager ever. Have you seen her music videos? Girlfriend may not have the best voice, but her music videos are legendary. Britney in a schoolgirl outfit? Britney in a red latex catsuit? Yep, we’re sold. Her world tours were crushin’ it. She performed during the Super Bowl Halftime show. She was on magazine covers. She earned Grammy nominations. She dated Justin Timberlake. She kissed Madonna at the VMAs. She was It.

Then, 2007 happened. If you Google “Britney Spears 2007,” you’ll know exactly what we’re talking about. It was a year that included Bald Britney and her trusty umbrella. Many people didn’t think there was any coming back from that, but Britney came back. She now has a wildly popular residency in Las Vegas that is reportedly earning her $475,000 a show. She managed to not shave her head, get arrested, or get married in the past few years. It seems that Britney is back. However, she can never truly be back. Her breakdown is something that taints her image, no matter how much effort she puts into rehabbing it. Yes, she looks great and performs with the same fire she once had, but we can all still recall Bald Brit with her umbrella.

Prior to 2007, Britney was on top of the world and there were no bat-shit crazy photos to blemish her image. She was truly perfect. That was when Britney was in her prime. Here are 18 photos to remind you just how on top of the world ol’ Britney was at such a young age.


This shirt is not practical in any regard. In fact, we’re betting that a chain mail shirt is pretty uncomfortable and quite chilly. Also, the fact that it’s only being held together by two delicate chains means Britney can’t do much in it. A slight breeze passes and Brit could be showing much more than she wanted.

Practicality aside, this photo is vintage Britney. Between the purple eye shadow and glossy lips, she is reminding us just ridiculous some of her looks were... but she still looked perfect. She actually thrives in these early 2000s styles. Oh, and her body is amazing. We’re pretty sure that belly piercings surged 200% from Brit flaunting her always-taut stomach, and belly button ring. Unfortunately, getting a belly button ring doesn’t automatically make you as hot as Britney. There is only one Britney.

8 As A Gladiator With A Belly Ring


Back in 2001, Britney struck an endorsement deal with Pepsi for a whooping $8 million. Considering how iconic the Britney/Pepsi advertisements were, $8 million was actually a steal. While they worked several different marketing spins, the most memorable is Gladiator Britney. How could you forget this commercial? Some people (totally me) would watch TV just hoping this commercial came on.

In it, Britney, Beyonce, and Pink come into a gladiator dome and sing “We Will Rock You." This is all while drinking Pepsi, of course. A mandate for casting must have been something like, “Singer with abs of steel.” All of these ladies have washboard stomachs. While Britney rocked her sexy-Gladiator look, our favorite part is that she’s still wearing her belly button ring. You can take Brit out of 2001, but you can’t take the belly ring out of Brit.


When Britney Spears first hit the scene, she really milked the wholesome thing. In fact, the “...Baby One More Time” music video was originally supposed to be cartoonish to appeal to a young audience, but Britney had a better idea. She pitched her own concept of it being at a school with lots of dancing. They obviously went for this idea, since it is now what we know as the iconic video.

Hold on, Britney is even more genius. Upon looking at the wardrobe, which was a t-shirt and jeans, she then pitched the schoolgirl idea. Again, they went for it. It gets better. She thought the uniforms were too dorky and suggested everyone tie up their shirts. Basically, Britney was the mastermind behind the whole music video, which launched her entire career and brand. People often underestimate Britney, but girlfriend is in tune with what to give the public.

This photo is from a shoot with Timothy White in 1999. She’s obviously still milking the sweet as apple pie thing, which was always part of her appeal. Britney was always both the girl next door and, uh, the type of girl who dances with a snake around her neck.

7 That Rolling Stone Cover


In 1999, Britney graced the cover of Rolling Stone for the first time. It would become an iconic photoshoot, both for her and Rolling Stone. This particular photoshoot really encapsulated what was so interesting about Britney. She was 18 years old and somewhere between being a girl and a woman – y’know, as she would sing about later.

The cover photo (above) showed the teenage Britney in her underwear while holding both a telephone and a Teletubby. It is rubbing both her sexuality and innocence in your face. It was about this time that the American Family Association condemned Britney. They said that the photoshoot was disturbing because of the way it mixed young innocence and adult sexuality. Uh, that was kind of the point, guys. The AFA urged people to boycott Queen Brit. Obviously, the AFA didn’t make that much of a dent on her career.

6 That Other Rolling Stones Cover


Britney Spears went on to grace the cover of Rolling Stone several times. She's worn a t-shirt and jeans on the cover, a bra and jeans, an American flag shirt and red leather pants. She also wore just underwear and what seemed like a bed sheet.

In 2003, she graced the cover in the above photo, which really, really showed off the curves of her body. 2003 was way past the days of her youth. She had already publicly broken up with Justin, supposedly for cheating on him with a back-up dancer. Britney was no longer the girl in a school uniform. She was a woman.

That year also saw the release of her 4th studio album, In The Zone. This album would produce four singles: “Me Against the Music,” “Toxic,” “Everytime,” and “Outrageous.” While everyone remembers Britney’s “Toxic” video (how could you not?), it was her “Everytime” video that really had critics talking. In it, Britney plays a star, who suffers under the stress of the media, dies, and is resurrected into a baby who was born at the hospital. It was oddly prolific considering how Britney would soon struggle under the weight of stardom.

5 No One Has Ever Looked As Good In A Green Bikini


You don’t see many green bikinis. Green can be a difficult color to pull off, especially in bikini form. Britney’s always-tanned bod and honey blonde hair makes it easy for her to look good in just about any color. Seriously, she can wear anything from a red latex catsuit to this green bikini. It also helps that her body is perfectly sculpted.

This picture is included because it is, again, vintage Britney. While she is flaunting her amazing body, her face is anything but sultry. She is wearing minimum makeup and has the wind blowing through her hair. Her mega-watt smile isn’t seducing anyone. It more looks like a carefree smile of someone about to jump into a lake. Yet, she’s still seducing anyone who looks at this photo. It’s this duality that made Britney a star. Oh, also she’s rocking her belly ring because duh.


Britney with the crimped hair was everything. She somehow pulled off crimped hair, even though no one pulls off crimped hair. This resulted in a ton of people copying her style – think of her herds of young girls who crimped their hair in the early 2000s. Little did those young girls know that Britney with crimped hair is much different than the rest of the world with crimped hair.

She rocked crimped hair at awards shows, photoshoots, and in music videos. This photo is a great example of Brit rocking something that would look good on no one else. If you ever saw a girl in real life with half-curled and half-crimped hair, you’d just think she looks... well, she wouldn't look like Britney. That's for sure.

For whatever reason, Britney looks hot. It also helps that she’s wearing a tiny jean skirt and midriff-bearing tank. Also, I spy a belly ring.


This photo may be the height of Britney doing the wholesome thing. She's just chillin’ in a field of flowers. She looks just about as youthful and innocent as anyone can possibly look. See? This was her appeal. You’d see this photoshoot, but then you’d also see Britney shimmying in a schoolgirl outfit. It was all so confusing, and all so hot.

The issue with this specific appeal is that it’s difficult for someone to keep up long-term. Britney Spears is now 35 years old. She can’t do that sweet, small town girl thing anymore. We all know Britney has been through some shit. In a genius way, Britney does dip into a mature wholesome angle through her social media posts. On her Instagram, she posts photos of her family, photos of goofy selfies, motivational quotes. Britney will even post pictures of goddamn kittens on Instagram just 'cause she thinks they're cute. It’s a new version of her wholesomeness, as she can’t play the wide-eyed young thing anymore.


We couldn’t not include this photo for several reasons. First of all, look at her. The "I’m a Slave 4 U" period was when Britney’s abs were at the top of their game. We know, we know. Girlfriend always had abs. That’s true, but at this point in her career, she was cut. There is barely any fat on her entire body.

This particular performance was at the 2001 MTV Video Music Awards. We could focus on how hot she is, because duh. Instead, let’s talk about what a performer she is. Girlfriend went on live television with an albino python on her shoulders. I probably wouldn’t put an albino python on my shoulders… like ever, especially not on live television. Britney is a badass, who is willing to do anything to give fans a show. This is why she has endured as one of the most successful singers of all time.


Britney’s performance with the snake outshined the "I'm a Slave 4 U" music video. I mean, she was carrying a snake around on live TV. There was obviously a ton of buzz around that. However, the music video is not to be overlooked.

Britney pumped out several iconic music videos in her time, but this may be the sexiest of all her videos. First, there’s her body. Like we said, this was the top of her ab game. There is also the fact that everyone is dripping in sweat in the video. It looks like a hot yoga studio. If you think about it too much, it’s not actually very sexy with all the sweat, but at face value it's hot. The sweat was apparently tasty too, since someone straight up licks Britney’s face in the video. Lastly, sweaty Brit was wearing her underwear outside of her pants. That may not have been all that practical, but she was sex on a stick.

If you had to show an alien one music video to describe what “sexy” is, it would be this video.


This picture has so much Britney going on, it’s amazing. First of all, her half-crimped hair again – YES! We don’t know who kept telling her to rock this hairstyle, but we’re so happy about it. Also, we have no idea what her shirt is doing. It’s pink and see-through. In fact, you can see her bra though it. We’re not even sure why she’s wearing a shirt. Half the time, she’d be in bikini top, so what’s up with the see-through shirt? We don’t know. Okay, moving on.

We’re super into whatever denim she’s rocking below. It looks like it’s folded down, so it may be shorts, a skirt, or jeans. We have no idea. Does it matter? Nah, not really. She still looks hot. Finally, we have her famous belly ring. It may be the most famous belly ring in all of history. No, seriously. Has anyone ever rocked a belly ring more? We don’t think so.

Oh, and the lips necklace! What is that! It's so bad and so Britney. We love it.

4 Covered In Toilet Paper... And Still Hot


What is this picture? We don’t know. There are the two things making Britney almost unrecognizable – her head is turned. We know it’s Brit (in 2016), but we are only getting the side profile. The second thing is the lack of the belly ring. Where is her famous belly ring? Was she like, ‘Oh, I’m mature now. I better take my belly ring out, even though I’ve been photographed with it in for, like, a decade’? We don’t know her thought process and we’re slightly disappointed that she doesn't have her belly ring in. It’s the hottest stomach piercing in history.

Moving beyond that, her body still looks phenomenal. Like, absolutely amazing. As good as in her prime. However, who the hell styled her? Why is she wearing a bunch of fabric wrapped around her body? She looks like a girl who wrapped toilet paper around herself so she could be a mummy for Halloween. She’s so hot that she still looks good with fabric dripping off of her body.

3 A Very Cropped Crop Top


Alright, this might be the hottest Brit. This was after she shed her good girl image. She didn’t go full-on X-Tina, aka Christina Aguilera circa Dirrty. Also, have we ever uncovered the mystery as to why X-Tina spelled "dirty" as "dirrty"? Why the extra R? The X-Tina era was a drastic change. What was so fascinating about Britney was that she shifted into womanhood all while still being Britney. Much of her brand was still the same, but she has just shaken free of the schoolgirl we were introduced to in 1999.

If any picture shows Britney fully indulging in her sultry, southern side, it’s this photo. She’s wearing the most cropped crop top of all time. She’s still sporting her signature tanned skin, blonde hair, and tight stomach. Oh, and of course – her belly ring! Yas, queen of belly piercings. We love it. Her denim shorts are super short and unbuttoned. We get it, Brit. You’re sexy. Your necklace is longer than your shirt. You're a woman now.

2 When Britney Won The Super Bowl


There was nothing better than Britney in 2001. Between her Pepsi deal, her hit albums, and the fact that she was the hottest thing in the world, Britney had it all in 2001. All included the Super Bowl Halftime Show.

Of course, Aerosmith and N Sync were the headline performers. But, for the finale, Britney, Mary J. Blige, and Nelly joined them to perform “Walk This Way”. Some of the performers she shared the stage with are legendary, but look at her abs! This was 100% Britney. She had random braids in her hair, a cut up shirt and shiny NFL pants on. OH, and she also rocked a random sock on her one forearm. It was weird, but Brit pulled it off. The best part was that this was while Britney and Justin were dating. If you watch the performance, she even smiles every time he sings. Was there ever a cuter couple?

Also, belly ring!


We’d love to post the entire "Oops!... I Did It Again" video, because it was epic. Britney. In a red latex catsuit. Say no more. She also rocked a white, cropped turtleneck outfit too, which was totally hot. No one remembers the white turtleneck number, though, because the red catsuit was everything. Apparently, the catsuit was Britney’s idea. See? We told you that she had a sixth sense about what would hit. Per Brit’s orders, the costume designer had to stay up all night to make her catsuit. Uh, thank heavens they did, because it will go down in pop culture history.

This video was also at the edge of her wholesome image. With lyrics in this song like "Oops! You think I'm in love/That I'm sent from above/I'm not that innocent" Britney was both indulging her audience in sweetness but easing us into her sexy transition.


Here is Britney Spears looking hot as hell. Slightly past her wide-eyed, innocent phase, she was embracing the sultry side, all while wearing a cardigan. Of course, she forgot to button her cardigan, whoopsies! Her shorts (or skirt?) was the shortest thing in the world. She could have been wearing underwear. Her body was flawless. And, you know what we’re totally going to point out right now, right? Her belly button ring! Always and forever. Forget The Beatles. The best group in history is Britney, her abs, and her belly ring.

Also, here is a prime example of how Brit mixes the sweet and sexy today. She posted this photo on her Instagram recently, with a caption that read: "My friends sent me this picture today... and it's weird because I just realized it's one of the only pictures I've ever taken upside down!" The photo is hot, but the caption said something about how goofy it is because it's upside down. That’s Britney – she posts something smokin’ hot but is like, ‘Golly gee, y’all, I’m upside down!’

1 When She Was Like, "Hey World, I'm A Woman!"


While this picture gives you the gist of the performance, if you haven’t seen it, check it out. Britney comes out wearing a suit and singing “(I Can't Get No) Satisfaction.” She then removes her suit to reveal a nude, sparkly outfit and sing "Oops!...I Did It Again." Her performance is flawless. Does she have the pipes that some of the other greatest pop stars have had? No, not by a long shot. But try, just try, to take your eyes off the screen as Britney performs. She is entertainment at it’s finest.

Also, can we talk about how genius Britney was? She used this performance to rebrand herself. Before this, she was the schoolgirl from “...Baby One More Time.” She was bubble gum. She was southern sweetness. She was apple pie with a belly ring. This was her saying, “I’m a woman and I'm sexy.” She was done with being seen as the good, little girl.

Using a VMA performance to rebrand would be a move that Miley Cyrus stole from Brit. Why did Miley follow in Brit’s footsteps? Because it friggin’ worked. No one thought Britney was a sweet, young girl after watching this performance. She was powerful, sexy, commanded the stage, and owned everything she touched.


We’ll finish with this photo, taken before her 2000 VMA performance.

It’s the most perfect example of the Britney paradox. It’s both innocent and remarkably sexy. She is wearing a pink tee shirt that's tied up. With the addition of her black, leather pants and tight stomach, she’s walking sex. However, her face is fresh and happy. She isn’t batting her eyes at the camera. She’s smiling like it’s the goddamn prom. This is what Britney Spears tapped into in a way that no one will ever be able to tap into again. It was a different America. It was an America that was reeling from the Bill Clinton/Monica Lewinsky affair. Sex was not being served up in such a blunt way, especially by a teenage girl. Then came Britney Spears.

Since Britney, we’ve had different versions of pop stars. Taylor Swift taps into the wholesome aspect, but fails to be even a teardrop as sexy. Lady Gaga can do theatrics like Britney, but nothing about Gaga is ever wholesome. Katy Perry is sexy and rocks bubblegum pop tunes, but taps into a pin-up vibe instead of innocence. This mixture of sexy and sweet is what made Britney so desirable and entertaining in her prime. While we still love Britney, nothing will ever top Britney in her prime. It was truly lightning in a bottle.

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18 Must-See Photos Of Britney Spears In Her Prime