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15 Photos Of Britney Spears When She Looked Downright Ugly

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15 Photos Of Britney Spears When She Looked Downright Ugly

When Britney Spears first started out on The Mickey Mouse Club, no one could have guessed that she would end up as one of the world’s most well-known performers. She became known as the Princess of Pop and became beloved all over the world. There was a time when Spears was one of the hottest pop stars in the music scene, with best-selling albums and hit singles that spawned some of the sexiest music videos of her era. Yet, things weren’t always bright and sunny for Spears as she faced struggles in her personal life. Many have blamed her problems on the fact that she achieved such a large amount of fame at an early age. People have speculated that this is the main reason why she couldn’t seem to cope with all of the stress that fame brought. From constant breakups to custody battles and weight gain, Spears quickly went from a hot pop star to a hot mess in the eyes of the public.

While much of her early career in the music industry was filled with super sexy music videos, pictorial shoots and stage performances, there were also an equal amount of extremely unflattering photos that surfaced later on in her career. She was often photographed looking disheveled and completely uncaring about her physical appearance, which caused many to wonder whether or not she would ever be thought of as the once-beautiful pop star of her youth. Check out our list of the 15 photos of Britney Spears when she looked downright ugly and see how even the most beautiful music artist can have her fair share of unflattering moments in front of the camera.

15. Taco Bell And Driving

While regular people are known to partake in some fast food drive-thrus on occasion, celebrities aren’t really thought of as people that frequent fast food venues. While there have been some celebrities that have mentioned their craving for fast food items at award show red carpet events, the public doesn’t picture them actually eating greasy food in their cars. Yet, Britney Spears has been known to do just that on more than one occasion. In this particular photo, Spears can be seen chowing down on Taco Bell and it’s not a pretty sight. At one point, the photo shows her slurping up some loose cheese that is desperately trying to get away. Not only are her eating habits completely unappealing, but her disheveled look and makeup-free face isn’t helping out the situation at all.

14. Bad Hair Extensions

While hair extensions used to be a secret in Hollywood, nowadays the world knows all about the little tricks celebrities use to try and appear like they have full and luxurious hair. The Kardashians are often photographed in-between hair extension visit and Wendy Williams has been very open about her love of wigs. However, an issue that many people have regarding hair extensions is the fact that it requires an incredible amount of upkeep. Obviously, it was just all too much for Britney Spears since there have been numerous photos of her over the years with a completely jacked up look due to her bad hair extensions. It’s difficult to say why she would want to draw more attention to her jungle-like locks by putting her hair up in a ponytail but it doesn’t look like she was putting much thought into it in the first place.

13. 2007 VMA Performance

There was a time when Britney Spears was the hottest pop star to perform on stage at an award show. From her snake performance for “I’m A Slave 4 U” to the infamous onstage kiss with Madonna, there was a high standard when it came to Britney Spears performances. Yet, all of that was demolished during her 2007 performance at the VMAs. She appeared in fishnet stockings and a rhinestone bra and panty set with black detailing. While this would have been completely appropriate for Spears during her heyday, she no longer had the same physique and it wasn’t a flattering look to have so much skin revealed. Rolls of fat could be seen whenever she moved and the bottoms cut into her sides to give her a pronounced muffin top. As if that weren’t bad enough, her hair looked like a wet mop that was doused with a great deal of hairspray.

12. Overweight London Performance

Prior to Britney Spears receiving a residency in Las Vegas, she would make the bulk of her income through touring dates around the globe. However, there was quite some time that went by where Spears was no longer considered a great stage performer. When fans buy Britney Spears’ concert tickets, there is a certain standard they have in their minds regarding what the performance should look like. In 2011, Spears was performing in London and was highly criticized for her appearance during the show. She wore a pair of ripped denim shorts with pink rhinestone accents that matched the rhinestone-studded bra. While the ensemble was bad enough with a dated look and unflattering style, it was her overweight form that really stole the show. Spears looked far from her younger self onstage and many questioned what would have driven her to wear such a skimpy outfit when she was no longer in the shape to wear it.

11. Bald And On The Attack

This umbrella moment with Britney Spears is unforgettable in the minds of fans since it showed her in a completely broken down state of mind. With a clean-shaven bald look, she can be seen on full attack of one of the cars owned by the paparazzi at a gas station. She began attacking the car with the infamous green umbrella and was reportedly screaming expletives while she did it. It’s difficult to say what the ugliest elements were in this moment. While her sweat suit-style ensemble was bad enough and the bald head definitely put it over the top, the fact that she could go into a full-on meltdown made her look even uglier. To be fair, this moment in February of 2007 was an extremely difficult time for Spears since she was in the middle of a bitter custody battle with Kevin Federline. However, she is undoubtedly still kicking herself for letting the paparazzi get the best of her in these photos since they will live on in infamy for the rest of her career.

10. Shopping At The Mall

While going to the mall is a regular occurrence for some people, others dread the experience and avoid it as much as possible. Although there isn’t an established guideline on how people have to dress, the general rule is that the people should look somewhat ready to be seen by others walking around and shopping. Britney Spears must have missed the memo and she decided to walk the shopping area wearing gigantic oversized sweatpants and a tank top with a “Rehab” motif. It’s obvious that she’s not wearing a bra beneath her ill-fitting white top and from the dangerously low cut of her pants, she may not be wearing underwear either. Her hair is pulled back in a sloppy ponytail and she doesn’t seem at all embarrassed by the fact that she looks like a hobo in the pictures. Instead, she seems completely unbothered and is even seen partaking in a few store sales while she roams the mall.

9. Grabbing A Frappuccino

While it’s nice to see a celebrity doing something so regular like going out to get some Starbucks, this photo shows a shocking moment in 2010 when she looked downright ugly. It’s hard to say what is truly going on with her hair since it could easily be a tangled mess of weave atop her head. However, it could also just be that she hadn’t run a comb through it in quite some time. Whatever the case, fans would have been much more satisfied to see her in a hat rather than reveal the bird’s nest on her head. Yet, the worst part of her look was the facial expressions she used while walking. While the world doesn’t expect her to have a plastered smile on her face the entire time, some of the expressions she chose to don were very unflattering. Perhaps she was wearing a scantily clad ensemble to try and bring the attention away from her face and hair but that was almost impossible.

8. Walking With Kevin Federline

Britney Spears’ fans always seem to hold the years of her dating Justin Timberlake close to their heart, which is probably why there was so much animosity towards her relationship with Kevin Federline. Timberlake famously alluded to Federline being the reason why his relationship with Britney broke down and fans didn’t like seeing her with this new boy-toy backup dancer. Yet, that wasn’t the only reason why fans aren’t too big on the Kevin Federline phase of Britney Spears. While they were only married for two years, many of the photos of Spears during that time weren’t very flattering. In this particular photo, Spears looks completely disheveled as she walked with Federline and the two looked almost comical in their outfit choices. This is not the Britney Spears that fans were used to and it definitely wasn’t a good look for the Princess of Pop.

7. Every Trend At Once

When it comes to the latest in fashion trends, celebrities always seem to have the inside scoop on what the hottest new fad will be. This is especially true since designers often send new products to celebrities to try and get them to be photographed with it and thus helping with product sales. Yet, not all celebrities can pull off certain style trends and not all of them know how to put together a correct ensemble on occasions. This photo is a prime example of that since Britney Spears chose to throw as many trends into one outfit as possible. While the Bohemian chic style can be extremely flattering, this frilly white dress isn’t exactly giving off that vibe. Instead, it’s extremely ill-fitting and could stand to be jazzed up a bit. Rather than keep her hair flowing and flirty to go along with the dress, she tucked it into a hat with a bold purple ribbon to make it stand out even further. The pièce de résistance are the Uggs that bring down the entire look. While she may have been trying to look like a trendsetter in her style, she wound up looking more like a hot mess.

6. Handkerchief Top

The world of the rich and famous is usually filled with dining at all the hotspot locations and shopping for luxury brands. The paparazzi are always getting snaps of celebrities holding their designer handbags and appearing ultra glamorous but that definitely wasn’t the case for Britney Spears in this particular photo. While shopping in Los Angeles, Spears had her picture taken while looking ultra pale. Although it was taken on a sunny day, Spears looks downright pasty in her skin tone and it doesn’t help that she’s wearing a white and khaki ensemble. It only washes her out even further and the cut of the top is completely unflattering. The strapless style makes her breasts look saggy and her upper body flabby. She completed the ensemble with a pair of black flip flops and a disheveled hairstyle.

5. Shaving Her Head

While everyone remembers the 2007 incident involving Britney Spears going crazy on the car of the paparazzi with an infamous green umbrella. Yet, the photos showing her actually getting her head shaved can sometimes be forgotten. At one point, Spears can be seen taking the razor in her own hands and shaving off her hair to a completely bald state. There were a few different theories regarding her reason for wanting to shave her head so it’s up to the public to decide for themselves. One excuse was that the years of extensions and hair clips had destroyed her hair and she wanted to start off fresh with a completely even cut to ensure healthier hair. Another reason that floated around was that she was trying to get rid of any drug evidence that might come up during the custody battle she was facing at the time. Fearing that her hair would be tested for drug use, it was alleged that she shaved her head to get around the drug testing. Others believe that she shaved her head because she was going through a mental breakdown and wasn’t thinking clearly. Whatever the reason, the photos of her taking a razor to her own head with a maniacal smile on her face were nightmare-worthy.

4. Picking Her Nose

Britney Spears has been caught doing a number of questionable acts in cars over the years. From her unappetizing moments scarfing down fast food behind the wheel to getting out of the car without panties to her baby riding in the car without a car seat, there should be nothing that would surprise the public regarding Britney’s driving habits. However, this photo has taken her driving habits to a whole new level. While the public may want to believe that this nose-picking photo is just an isolated incident, there were actually court documents that referenced Britney’s alleged regular nose-picking habits. In 2011, Britney’s former bodyguard, Fernando Flores, filed a lawsuit against Spears and mentioned a number of things he allegedly witnessed while in her employment. He reportedly claimed that she constantly picked her nose, frequently skipped showering and even alluded to drug use.

3. X-Factor Judge

When The X-Factor was trying to create a successful series in the United States, there was a lot of pressure for them to achieve the same kind of viewership that the series has in the UK. In the pursuit of trying to garner a huge audience, Britney Spears was asked to participate as a judge. While there were some episodes where Spears looked pretty healthy and almost back to her former beautiful state, there were many other times where she appeared nothing like a pop star. In this particular photo, Spears looked incredibly old and rundown. Her complexion appeared orange-like in its tone, her dark roots made her hairline appear strange and her lips seem practically non-existent. To make things even worse, her makeup has a smoky-eyed look only on the bottom so she looks extremely tired rather than glamorous and beautiful.

2. Ranch Uggs

Britney Spears is generally thought of as a blonde, even though she’s donned a number of different hair colors over the years. She’s had a number of brunette moments during her personal life and has been almost every color in music videos. Yet, the times when she had darker hair weren’t exactly a favorite amongst her fans. In this particular photo, her dark hair had a bit of an auburn tone but it wasn’t very flattering against her skin tone. To make things even worse, she had a ranch-like ensemble that made her look like a spare farmhand rather than a pop star. The denim shorts were ill-fitting and had a fringe cut on the bottom that made them look like something cheaply purchased at Walmart. To complete the ensemble, she sported the entire outfit with her signature Uggs.

1. The Ugly Cry

While no one expects celebrities to look drop dead gorgeous when they’re in the middle of crying, it is a little surprising when they go into the full-on “ugly cry.” Oprah Winfrey once talked about this when she was referencing how emotional some of her episodes were on her talk show and Kim Kardashian has quite a lot of memes that feature her “ugly cry” moments. In this particular photo, Spears is obviously having a bad day and she’s not exactly looking her best. To be fair, the paparazzi constantly hound celebrities and often provoke them to try and get a picture out of them that will garner the best results for the purpose of selling tabloids. It’s obvious that she was being hounded by someone since she can be seen sticking her tongue out in one photo and bawling crying in another. In any case, she’s probably wishing she stayed home on this particular night because these photos definitely didn’t do her public persona any favors.

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