15 Times Katy Perry Looked Downright Ugly

When Katy Perry had her breakout moment after her hit single, “I Kissed A Girl,” the world wanted to know all about her.

When Katy Perry had her breakout moment after her hit single, “I Kissed A Girl,” the world wanted to know all about this brand new beauty on the music scene. She was able to parlay the success from her single to a number of subsequent successful songs and albums and became a staple at award shows looking for a hot performer. Her music videos became a talking point about her sex appeal and she became a celebrity to look out for whenever there was a red carpet event. Yet, with an increased amount of fame, also came an increased amount of scrutiny over her past and present. It was revealed that the album that everyone thought was her breakout moment was actually not the first time she had released a studio album. In fact, she had already got her start in the music industry when she first started out as a Christian Contemporary artist.

This previous album didn’t do well at all and Perry ultimately had to change up her entire persona in order to become the music star she always wanted to be. She ultimately became one of the most successful artists in the music industry and was even asked to perform during the Super Bowl Halftime Show in 2015. Yet, all of that fame and success can’t make the photos from the days of her early career go away and it also can’t help her from making some mistakes in her current look. Since Perry is known for being highly done up whenever she performs or goes to a red carpet event, she has unwittingly set the bar pretty high on how her fans expect her to look. Check out our list of the 15 times Katy Perry looked downright ugly and see that she has had her fair share of missteps over the years.

15 Christian Rock Album

One of the elements of Katy Perry’s professional career that may surprise fans is the fact that she previously released an album under the name, Katy Hudson. When she emerged with the breakout single, “I Kissed A Girl,” off of her 2008 album, One of the Boys, the public simply assumed that this was her debut studio album. This was a bit of a debut for Perry since it was a completely different persona from her early life. Her first album featured Christian rock music and she had a much more natural look. However, not all of the promotional photos for her first album were flattering. In this particular photo, it looks like Perry accidentally got mowed over while lying on the lawn, with the haircut to prove it. The choppy cut looks more than a bit unruly, which is a stark contrast from her practically tattooed-on eyebrows that look painted on. Her chin looks altogether too full, which makes her face look overweight and disproportionate to the rest of her body.

14 Military Look

The music industry has become increasingly volatile in recent years and it can be especially difficult for artists to make money through album sales. With digital downloads and bootleg streaming sites, people aren’t spending money on buying music like it was in previous years. It takes a truly special album for a music artist to create profit from it and it shouldn’t surprise people that an artist would want to make the most out of a successful album. Perry realized this when she reissued her successful third studio album around two years after its initial release. Teenage Dream: The Complete Confection offered devoted fans a few extras that made them want to buy it. One of the additional songs on the album was “Part of Me.” While the premise of the song was extremely empowering, Perry’s look for the music video was far from flattering.

13 The Street Walker Look

It isn’t a new concept for a celebrity to don some striking heels to go with a pair of ultra-short shorts but this photo shows that there is definitely a right way to do it and a wrong way. Typically, heels can help to amplify the glamour of an ensemble, especially if it is an outfit that shows off the legs. Yet, this look was far from glamorous. Instead, the yellow heels only made her legs look even pastier and it wasn’t the great pick to bring out the drag tones in the rest of her ensemble. To make things even worse, Perry’s hair looks like it hasn’t been washed in a few weeks and she looks more like she just rolled out of bed. This may have been an attempt at looking casually sexy but it definitely missed the mark.

12 Tribal Ensemble

When Katy Perry was dating John Mayer, the world had a number of reservations since Mayer had been previously linked to a number of celebrity starlets over the years. Yet, the couple seemed to be going strong and both of them looked like the best version of themselves whenever they were photographed together at red carpet events. However, like in any relationship, there comes a point when people start to get comfortable enough to let their true selves shine through. In Katy Perry’s case, this photo marked the beginning of the end to her relationship with John Mayer. While vacationing in Hawaii, the couple was seen playfully taking photos together and these photos of Perry were released to the tabloids. From the tribal pattern that completely washed her out to the ill-fitting cut that made her body look boxy, it’s difficult to even recognize Perry from her former red carpet looks.

11 Sans Makeup Tweet

When Katy Perry and Russell Brand became romantically linked, it seemed like it would be a long-lasting marriage (or at least by Hollywood’s terms). They seemed to have similarities that would make for a good union, so fans were pretty surprised when Brand filed for divorce in 2011 after only 14 months of marriage. There was a bit more insight into what led to the demise of their marriage in the documentary film, BRAND: A Second Coming, since it showed how Brand wanted his life to mean more than what the celebrity lifestyle had to offer. Yet, anyone that follows Brand on Twitter could tell you that the start of the end was when he tweeted a photo of Perry without any makeup. This was definitely a moment that should have stayed between husband and wife and he undoubtedly caught a huge amount of flack once Perry realized the photo was sent to the entire world.

10 Promoting Eye Makeup

In 2015, Katy Perry launched her eyelash collection in California. The Eylure lashes were supposed to promote full and beautiful lashes and Perry was supposed to be the perfect representative since she had already solidified herself as one of the hottest artists in the music industry. Yet, the look she chose for the launch event was far from depicting her as a super hot music artist. While the public had already seen Perry with turquoise hair, the different shades combined with the retro style was a bit much. To make things even worse, she completed the look with a completely blue toned ensemble. People dubbed this look akin to Smurfette and the only way it could have gotten any worse was if she donned a cross-eyed facial expression. It’s ironic that this is the pose she took in order to promote a beauty product for eyelashes.

9 Alien Look

When Katy Perry sought out to make her third album stand out from the success from the previous album, One of the Boys, she was undoubtedly under a lot of pressure not to be considered a one-hit-wonder. The album was released in 2010, which was during a time when Lady Gaga was garnering huge attention for her over-the-top ensembles and stage performances. Whether it was Perry’s attempt at trying to put herself in the same category of Lady Gaga or it truly was her way of transmitting her artistic expression, the video for the fourth single from the album showed Perry as a scary-looking alien. Although the song was entitled, “E.T.,” that didn’t necessarily require her to look similar to something seen from an Alien film.

8  8.  Photo Session In 2002

Prior to Katy Perry becoming the highly glamorized music artist that the world has become accustomed to seeing, she was actually quite plain in her everyday look. In fact, this photo shows that she didn’t even put much effort into her appearance when attending a photo session at a recording studio. This particular photo was taken in 2002 and shows Perry with an ultra-shaggy hairstyle that looks more greasy than styled. Her face is left looking natural but it only helps to highlight the darkness around her eyes and the flat tone to her complexion. From the ratty t-shirt to the Joker-like grin, this seems more like a photo of the unpopular kid trying to earn an invitation to the party rather than the glamour girl she has become.

7 Christian Contemporary Performance

When Katy Perry was first starting out in the music industry, she wasn’t the same pop artist that she has become today. Instead, she went the route of Christian Contemporary and she actually made it pretty far in that path. In fact, her debut studio album was in that genre and she performed on a variety of stages under the name Katy Hudson. In this particular photo, she can be seen performing on stage and she looks like a completely different entertainer than the world is used to seeing. Holding a guitar and performing with a band, Perry has never appeared as a folksy type of artist like this ever since she first “Kissed A Girl.” While the strange tie-like scarf and polka-dot top are bad enough, it’s the mop-like hairstyle that truly makes her look downright ugly.

6 Religious Met Gala Look

Every year in May, the Metropolitan Museum of Art Costume Institute holds a black-tie benefit to raise funds and awareness for the Costume Institute. This is a fashion extravaganza that celebrities are only too happy to attend but not all of the outfits wind up on the “Best Dressed” lists. For the 2013 Met Gala, Katy Perry attended wearing an ensemble from the fashion designer, Dolce & Gabbana. The designers were reportedly inspired by Sicily’s Cathedral of Monreale when designing the dress and it can be seen in the mosaic patterns and gold tones. While the dress really isn’t that bad for Met Gala attire, it was her hair and makeup that made the look unflattering. Her hair features some straightened portions and frizzed out ends to give the appearance of something similar to a poodle and the makeup was so dark that it made her appear scary rather than glamorous.

5 Silk On Silk

There are far too many things wrong with this photo to point out, which is probably why Perry hasn’t ever thought to repeat the look. The neutral tone to the top completely washes out her complexion and the straps seem to be digging into her shoulders while the rest of it balloons outward. Not only is it unflattering to her figure but the material obviously makes it impossible to keep free of wrinkles. She paired it up with a pair of silk pants that may have looked nice with a more fitted top but it’s impossible to tell. Her hair is put into a messy style that only highlights the choppy cut to her bangs and her makeup looks like someone stamped her cheeks with a bright pink stamp. Apparently, she must have been going for the baby doll look in this photo since the blush she used is electric compared to the rest of her face.

4 Mop Hair And Bad Part

Back when Katy Perry was starting to make the transition from her former Katy Hudson persona to her new more provocative look, there was a period where she hadn’t yet made the switch. She was stuck in a period of limbo and it wasn’t the best time for her physical appearance. She soon found out that the best look on her is “Go big or go home,” which is evident in this photo. The outfit actually isn’t that bad since it is reminiscent of her retro style that she tends to gravitate towards nowadays but she didn’t match it up with her hair and makeup. Instead, her makeup is minimal and her hair looks like it hasn’t been washed or combed in months. The part on the side of her head looks more like a bald spot and the bangs are so unruly that it looks like someone used a Sharpie to paint them on her forehead.

3 Boy Band Hair

Katy Perry has had a number of different hairstyles over the years and has even donned a few short haircuts that have become hugely popular. However, ever since she obtained breakout fame from her first hit single, “I Kissed A Girl,” she hasn’t cut her hair shorter than a long bob. This particular photo shows her long before her success as Katy Perry the pop star and shows her with a boy-band hairstyle. The bob cut is more than just a tad choppy and features even shorter layers toward the top. The bangs can’t seem to make up their mind if they want to be swept to the side or just drape over the forehead. Yet, the most disturbing part of the photo is the way Perry looks when she smiles. This was a common look for Perry before she got the hang of her more stoic look and the mix between a toothy grin and a tight-lipped smile really wasn’t doing her any favors.

2 Black Highlights

Katy Perry is a music artist that is known for being adventurous in her hairstyles and has probably changed her hair color more than any other artist in the music industry. Everyone seems to have their favorite look for Katy Perry, whether it’s her Bettie Page look or her turquoise hair. Yet, not all of her hair choices have been hits. During the early part of her career in music, Perry had a dirty blonde hair color that she paired with big black highlights. While it was trendy to have black highlights in the ‘90s and Gwen Stefani was able to add a few black tones to her blonde hair in recent years to create a signature look, this photo shows how badly it came together for Perry. While the Brady Bunch outfit is bad enough, the choppy haircut and chunky black portions of her hair look off-putting to say the least.

1 Corpse Look

Katy Perry has been known to seek out bold colors in her hair and makeup over the last few years but she usually gravitates towards lighter tones. From electric blue to turquoise to hot pink, she has flourished whenever she has turned to bold and light tones. Yet, this look is something completely different for the “California Gurls” singer. Her dark violet lip shade and darkened circles under her eyes make her look more like a corpse than a fresh-faced beauty and it is only further highlighted by the caked on foundation all over her face. There is almost a grey tone to her complexion and her hair looks stringy and unkempt. She completed the look with a black blazer that only made people think about what someone might wear to a funeral, which was completely adequate to describe this particular Katy Perry look.

Sources: Complex, Huffington Post, Page Six

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15 Times Katy Perry Looked Downright Ugly