Love or hate her, it’s abundantly clear that Britney Spears has been one of the most talked about celebrities since signing with Jive Records in 1997. She quickly captured the attention of millions with her catchy songs, but perhaps even more importantly as far as some people were concerned, her captivating good looks.
Spears has had several moments throughout her career where she has left little to the imagination, and in the process, left your imagination running wild! And as you’ll see on our list, despite it being 2018 and Spears is now 36 years old, she remains in perhaps the best shape of her life.
But for all the amazing moments in Spears life, come moments and looks that make you curious on if she looked in a mirror prior to leaving the house. Whether it was on the red carpet when she knew everyone would be looking, or caught by the paparazzi on what seems to be some of her worst days.
These were the 10 Times Britney Spears’ Fashion Choices Were Stunning (And 10 Times She Needed Help).
20. Stunning – Showing Support For The Dream Act
There are many things in Britney Spears life that she loves to try and raise awareness for. And while she may not be the most politically active celebrity, that doesn’t mean she’s completely afraid to voice her support for the matters that matter the most to her.
One of the most politically charged topics in 2017/2018 was the Dream Act which seeks to help give immigrants the chance to gain employment in America.
You don’t have to appreciate Spears’ music to be a fan of the fact that she’s taken her platform and used it to help make a positive difference in the world.
19. Not – Being Carried Out By Paris
There aren’t many celebrities in Hollywood who have a bigger reputation for knowing how to party than Paris Hilton. So when you look at this above photo and see that it is Britney Spears that is the one that needs to be carried out of the club, you may get an idea as to just how inebriated she may have been on this night!
Making matters worse, Spears elected to leave the bra at home for this night of drinking which was an idea she also learned to later regret. Especially because once the paparazzi realized she was drunk, they definitely didn’t stop taking photos! Though if there’s any benefit here, at least Paris probably knows some pretty wonderful hangover cures. But something tells us it probably doesn’t include blasting some Britney over the loudspeakers the next morning.
18. Stunning – Celebrating 2018 On The Beach In Hawaii
Britney Spears recently wrapped up her last show in her Las Vegas Residency contract where she was performing the last few years. As a result, she had plenty of reasons to go out and celebrate. And when you’re rich and famous, you can decide to go away for a vacation whenever your schedule allows for it.
Spears, alongside her two children, jetted off to Hawaii back on January 4th, 2018; a moment that was naturally captured by all the paparazzi in attendance. Spears uploaded a photo from the day to her Instagram along with the caption, “Me and my boys enjoying the warm weather!!!”
17. Not – When She Felt She Looked Like She Was Combusting
There have been many moments in Britney Spears life where she must have felt like the most attractive woman in the entire world. But one of those moments did not come after she performed at the MTV Awards back in 2007. Expected to be a big return to form, the end results were far from that and left many people wondering if her career was over. When describing her reaction to US Magazine, a source on scene said
“She flipped out. She came running off the stage, yelling ‘Oh, my God, I looked like a fat pig! I looked like a fat pig!’ She was inconsolable.”
16. Stunning – In Her Rolling Stone Photo Shoot
As captivating as Spears’ music was at the start of her career, Spears also quickly was making a name for herself as being one of the best-looking musicians in the industry.
In 1999, the same year as her debut album, Spears agreed to a photo shoot with Rolling Stone. Perhaps poking fun at her age, she was 19 at the time, the magazine elected to pair her with a Tinky Winky teletubby doll. While the magazine did garner some backlash from people who felt she was being oversexualized, the real takeaway from the photo shoot was the seductive style of Spears that continued to become apparent throughout her career.
15. Not – In Her Juicy Couture Tracksuit
If you look back at the early 2000s, you would see that one of the most popular fashion trends was wearing Juicy Couture tracksuits. But just because it was one of the most recognized senses of style, doesn’t mean it was a good look!
Spears was one of the biggest promoters of the fashion line. While the clothing does look incredibly comfortable, is that really enough to save the look? Many people with the power of hindsight sure don’t think so!
14. Stunning – For Women’s Health Magazine In 2015
Britney Spears started her career in 1999 with the release of the album “…Baby One More Time.” As captivating as her music was, Spears has always made a name for herself as also being one of the best-looking musicians in the industry.
While she’s engaged in various photo shoots throughout her career, perhaps your favorite one came back in 2015 when she appeared in Women’s Health magazine.
When talking about her fitness routine in the past, Spears has admitted,
13. Not – When She Was Accused Of Photoshop
There is no question that Spears was probably feeling great about her beach body when she elected to share the above photo with her Instagram followers back on March 20th, 2016.
But while the photo received over 200,000 likes, it also received an incredible amount of skepticism from people who felt that Spears photoshopped the image. There are photos on our list that prove Spears is in as good a shape as she appears in the photo, but the look of the edge of the pool underneath her back still raised some eyebrows.
12. Stunning – Showing Off In Her Favorite Type Of Outfit
There are many different styles of outfits that Britney Spears has rocked throughout her life that make an appearance on our list today. But when Spears herself was asked about her favorite type of outfit to wear, she elected to go with a more casual approach.
“I love my jeans and my sweats – I’m really just a tomboy at heart. So it’s really hard for me to be like Kim Kardashian and be makeup- and hair-ready every time I go out of my house,” said Spears in an interview.
11. Not – Smashing The Car With An Umbrella
Now if we’re being completely upfront, Britney Spears could be experiencing this night in the world’s sexiest bikini and it probably still wouldn’t have been a good moment. Because no matter what you are wearing, if you are taking an umbrella to the car of someone else, you aren’t going to come off looking good.
Combining the shaved head with the baggy sweater and you’re left with what was probably one of the worst moments of Spears’ life. There were many people who thought Spears would never be able to rebound from her meltdown, but as is shown from the stunning side of this list, she absolutely has!
10. Stunning – Praising The Paparazzi For This Swimsuit Snap
We’re sure that if the paparazzi never existed, that the world would have a very different view on Britney Spears. But sadly for her, they’ve always seemed to be there when she was going through some of her worst moments. She did, however, give some credit to the paparazzi for snagging this photo of her walking on the beach in a pink swimsuit.
Spears went as far as to actually upload the photo to her Instagram account, captioning it,
“The paps actually got a cool pic of me”
9. Not – Caught Looking Bad In A Grocery Store
If you were listing different clothing items that a woman could wear that would rev your engine, one of your dress shirts may be pretty high up on your list. But for Britney Spears, she definitely isn’t looking her best in our next entry.
It’s evident by the look on her face, that she definitely wasn’t prepared for her trip to the grocery store to become a new photo opportunity. Talk about a quick way to make sure you lose your appetite! Perhaps the biggest faux pas of the outfit comes not with her shirt, but the pink boots that she used to complete the look. At least her feet were probably pretty cozy?
8. Stunning – Embracing The ’70s For Pepsi
Kendall Jenner had hopes that when she appeared in the Pepsi commercial back in 2017, that she would find the same success as past celebrities who have stepped on board with the company. None of whom may have been more successful than Britney Spears who appeared in several high-profile ad campaigns for the company.
The above photo which features a festival-esque Britney was taken from an ad that ran during the Super Bowl and saw Pepsi being enjoyed through different decades (the above one symbolizing the 70s). While we don’t know how plentiful Pepsi was at events like Woodstock, if Britney was there selling it, we wouldn’t be stunned if there would be a lineup of people to get some!
7. Not – Taking The Bedroom To The Red Carpet At 2002 VMAs
It’s hard to wonder what kind of look Britney Spears was trying to go for back in 2002 when she attended the VMAs. Perhaps she was inspired by the fact that her music video for “I’m a Slave 4 U” was nominated that night for Best Female Video. The song was also featured as a single on Spears’ 3rd album, “Britney”.
And while Spears may have dressed for the attention, she may have wanted to disappear from the public eye after she ended the night empty-handed after losing to Pink. The loss didn’t exactly derail the career of Spears, but it’s probably not the most positive memory and doesn’t make this outfit any better.
6. Not – She Has The Golden Ticket (But Not The Outfit!)
We are sure that if Britney Spears had a time machine, that she would have definitely done things differently when it came to her relationship with Kevin Federline. And if she could really be picky, she’d also probably make sure this outfit got deleted from existence.
Worn to the premiere of Charlie and the Chocolate Factory, the decision to pair a silky skirt with that top was not one that many people found appealing. That being said, she was pregnant and we’re sure was just looking for relief in any way it could be found.
5. Stunning – Wanting You To Talk Nerdy To Her
If you had to guess which type of “man”, Britney Spears was into, you may guess that she likes men who are a little bit stronger. After all, she is dating Sam Asghari, who just happens to be a personal trainer. But just because Asghari seems to love hitting up the gym, doesn’t mean that he doesn’t have an intellectual side to him as well.
If he doesn’t, judging from this photo which Spears uploaded back on January 11th, he might want to start! We’re sure many of the 500,000+ fans who have already liked the photo would love to be able to talk nerdy to Spears.
4. Not – Crying On The Sidewalk After A Fight
Britney Spears had plenty of amazing memories with her former manager Sam Lufti. But she definitely had her fair share of awful moments, including him accusing her of a rampant addiction to amphetamines that led to her public breakdown. One of the tougher nights between the two of them occurred in 2008 and sadly for Britney, just happened to be captured by paparazzi.
Following an argument with Lufti in the car, Spears was photographed sitting on the sidewalk with tears streaming down her face. Her outfit wasn’t the best, but the situation made things go from bad to worse. We’re sure the fact that she had her puppy with her didn’t make the situation all the better, but at least she had someone with her to give her non-judgemental love!
3. Stunning – Showing Us Her Gym Body
There are many factors that go into being a successful musician. If you’re Britney Spears, you know that your ability to perform on the stage is going to be just as valuable as the music you release in the studio.
Which means that as much time as is spent making music, she better make sure she spends the same (if not more) time to make sure her body is in as good a shape as it needs to be in to get through a show. If the above photo (and her abs!) is any indication, it definitely looks like Spears and fitness are two things that go together very well. No wonder she’s able to do so much dancing and singing on stage!
2. Not – Inspired By The ’70s For Billboard Awards In 2000
Britney Spears is definitely familiar with people judging her for how she looks. So perhaps when the 2000 Billboard Awards rolled around, she just wanted to make as colorful a statement as she possibly could. And if that was her intention, it’s hard to say she failed at it. But instead of coming away with a stunning look, many people may feel like they’re experiencing some type of bad hallucinogenics if they stare at her outfit for too long.
She may have thought it did, but the matching hat does not help. Maybe she was just having a bad hair day? The similarly shaded undergarments may also not be doing a great job of selling people on the overall idea.
1. Stunning – Awarded Style Icon At Teen Choice 2015
Britney Spears had to feel a tremendous amount of pressure to be looking her best when she attended the Teen Choice Awards back in 2015. Especially when you consider she was later awarded the honor of being the biggest Style Icon. And standing on the stage with that award in your hand is definitely not when you want to have people talking about your awful fashion sense that night.
While sometimes the spotlight can produce some horrific outfits from Spears, that definitely didn’t seem to be the case on this particular night. Adding some fun color to her hair also helped her stand out, but in a way that didn’t look like she was trying too hard.
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