20 Cringe-Worthy Celebrity Halloween Costumes


Bubbling cauldrons and witches brew, moaning zombies and groaning ghosts, fright night is upon us! With Halloween only days away, many of us are running around trying to finish up our costumes, hang the last of the spider webs, and stock the candy bowls with treats! Others, however, haven’t even given Halloween a second thought. That’s what October 30th is for, right?

While most of us are on a budget for even groceries, it’s amazing to see the creativity so many have when it comes to Halloween costumes. From zombies that look like extras on The Walking Dead to Captain Jack Sparrow, many people prove that the sky is the limit whether they spend a small fortune or not. But, what about celebrities?

Despite their seemingly endless bank accounts and access to the world’s best makeup artists and costume designers, some celebrities have actually proven to disappoint when it comes to Halloween. From being lazy and offensive to tacky or boring, celebrities are not immune to horrible costumes. Don’t believe us? Well, thanks to their celebrity status, there are plenty of pictures to prove these celebrity blunders. Take a look at the 20 most cringe-worthy celebrity Halloween costumes of all time. Who has the worst? We’ll let you decide!

#20 – Angie Harmon

Hurry up! Someone call the fashion police! Actress and model Angie Harmon is no stranger to turning heads when it comes to her beauty and incredible sense of fashion but, this outfit left many scratching their heads. Did she even look in the mirror? With international fame for her roles in Baywatch Nights, Law & Order, and Rizzoli & Isles, Harmon spooked ever her most loyal fans with this costume from Halloween in 2002.

An eclectic collection of oddities, Harmon’s costume looks more like a battle between personalities (that, or she won a shopping spree to Hot Topic). With a hot pink wig, fish nets, chain suspenders, a plaid miniskirt and an unexplainable “Boy Beater” tank, we can’t quite tell what or who inspired Harmon’s look. Avril Lavigne? Britney Spears? Madonna? Either way, this costume definitely tanked!

#19 – Katy Perry, Cheeto

“Dangerously cheesy!” Known as one of the biggest names in the music industry, Katy Perry has not only sold millions of albums, she’s sold out countless venues around the globe. But, what exactly does America’s favorite “Roar” singer have in common with America’s favorite snack? Heartbreak and Halloween!

Perry stole the show at Kate Hudson’s 2014 Halloween bash when she showed up dressed as a Flamin’ Hot Cheeto! Wearing orange from head to toe and complete with a lumpy bodice, Perry’s makeshift purse from a Flamin’ Hot Cheetos bag was the only thing that hinted at the star’s costume choice. But, why a Cheeto? During her 2011 divorce from Russell Brand, Perry spent two weeks trying to cope and dulled her heartache with food (cue the Flamin’ Hot Cheetos) and liquor. Needless to say, the flamin’ hot Perry has since moved on.

#18 – Taylor Swift, Pegacorn

Not just another fearless fairytale! Speaking of big names in music, perhaps there is no bigger name right now than Taylor Swift who has successfully transitioned from country music star to pop sensation. Shattering records when it comes to tour tickets and radio hits, Swift shows no signs of slowing down. Why would she when she’s having so much fun?

Considered a queen when it comes to social media, Swift shared this picture from Halloween 2014 with her 50+ million followers saying, “Cause, darling I’m a nightmare dressed like a PEGACORN”. On the heels of Katy Perry’s debut as a Cheeto at Kate Hudson’s Halloween bash, Swift arrived dressed as her own creation, a Pegacorn. A cross between a Pegasus, the mythical flying horse that helped Hercules take down Hades, and a unicorn, we can’t help but laugh at Swift’s quirky creativity. Seriously, check out those wings and that horn! She really does live in a fairytale after all!

#17 – Tori Spelling, Peacock

Daughter of legendary Hollywood producer Aaron Spelling, Tori Spelling made a name for herself after starring as Donna Martin on “Beverly Hills, 90210”. Since then, the actress has become both a reality television star and author with her autobiography, Stori Telling, debuting as a best seller. With life in the spotlight, Spelling and her husband, former costar Dean McDermott, spend their free time keeping up appearances and supporting causes like the Children Affected by AIDS Foundation.

During the Foundation’s 17th Annual Dream Halloween party, Spelling shocked the media when she arrived dressed as a peacock. Obviously spending more time on her makeup than much else, Spelling’s costume was definitely lacking when it came to creativity. While her legs looked like the bottom half of a Blue Man Group member, the rest of the outfit was far from glamourous with what many thought should have been over the top, feathers and all.

#16 – Hugh Grant, Stag

One of the sexiest men or stags alive? Hailing from England, actor and producer Hugh Grant has stolen the hearts of many as one of Hollywood’s favorite leading men with films including Four Weddings and a Funeral, Bridget Jones’s Diary, Mickey Blue Eyes and Notting Hill. Though Grant’s silver screen career has since slowed down a bit, he’s still sharing his charming sense of humor and good looks with plenty of appearances in the public eye.

Grant made a special appearance at the star-studded 2014 UNICEF Halloween Ball to help raise money for Every Child in Danger and, thanks to his costume, we have no doubt he did exactly that. Dressed as a stag in just an oversized mask and a suit, Grant most likely won the prize for the cheapest costume at the event! Though critics praised Grant for his creativity and sense of humor, we can’t help but think this was a last minute lame purchase!

#15 – Mariah Carey & Nick Cannon, Cookies & Milk

Someone get Santa on the phone, we found his milk and cookies! Before the drama that ended Mariah Carey’s and Nick Cannon’s marriage, the power couple was actually one of the biggest and most loved in Hollywood. As the best-selling female musician of all time and the host of “America’s Got Talent”, everyone thought these two went together like peanut butter and jelly…eh, we mean, milk and cookies!

Showing off their creativity in 2008, the star couple’s costumes told the world what many already knew – these two were a perfect match. But, with Carey obviously getting the better deal when it came to costumes, we can’t help but see why the couple might have headed to splitsville. As Cannon was stuck sweating it out in an oversized cardboard milk box, Carey paraded around the party in a skin-tight latex suit with cookies glued to her body and even stuck in her bra. Perhaps Cannon didn’t have much say in this either!

#14 – Jessica Alba, Dora the Explorer

Let’s go on an adventure! Landing her first big Hollywood break at just 13 years old on “Dark Angel”, Jessica Alba has become one of Hollywood’s favorite leading ladies, not to mention an incredible businesswoman. Starring in films such as Sin City, Fantastic Four and Good Luck Chuck, Alba was also named as the Sexiest Woman in the World in 2007 but, would her title still hold true after Halloween 2009?

Attending the famous Halloween party hosted by Heidi Klum at the Voyeur Nightclub in Los Angeles, Alba arrived in full Dora the Explorer costume. Only, this Dora seemed to be far sexier than the cartoon. From her black wig to her fitted hot pink shirt and orange short shorts, Alba definitely turned the G-rated Dora up a notch. Though the costume itself is pretty simple, especially when you’ve got millions to spend, Alba and her husband, who dressed as Diego, made one heck of a pair at the biggest Halloween party of the year.

#13 – Aaron Carter, Pimp

Show me your swagger! The late 1990s and early 2000s proved to be the age pre-teen music as stars like Aaron Carter sought to make their way onto radio airwaves. With his older brother Nick as a Backstreet Boy, Carter seemed to have the upper hand on making it in the music business. With hits like “Aaron’s Party” and “How I Beat Shaq”, Carter quickly made a name for himself among pre-teen and teenage audiences with his pop and hip-hop style.

But, in 2002, the 14-year old singer showed up to a red carpet charity event dressed like a pimp. Now, when you think of someone who hustles prostitutes for cash, the first thing you think of is a 14 year old kid from Tampa, Florida, right? Well, maybe not so much. Dressed in a lush purple suit lined in leopard, Carter wore a leopard hat and dollar sign sunglasses that screamed cheap. While we could probably accept the bad costume choice, we can’t help but think that Carter as a pimp probably isn’t the best role model for this obvious children’s Toys ‘R’ Us and Mattel event.

#12 – Snooki, Pickle

When it comes to Nicole “Snooki” Polizzi, the world has MTV to thank for the star’s introduction to reality television. First appearing as a contestant on MTV’s “Is She Really Going Out With Him?”, Snooki was soon cast on the 2009 pilot for “Jersey Shore”. Quickly considered as the breakout member of the cast, Snooki became a household name whose love of partying, booze and drama made viewers tune in each week for more.

Ever the drama queen, it was no surprise when Snooki hosted a Halloween party in Las Vegas in 2010 wearing a costume tribute to her favorite snack: Princess Pickle. While many believed the 4’8” tall reality star opted for irony and dressed as the Jolly Green Giant, she quickly dispelled the rumors with a tweet, “The Pickle Princess has arrived”. Dressed in a green flapper-style dress, cape, heels and even a sparkly tiara, Snooki paraded around the party holding a scepter with a giant pickle on top. There’s no denying this star loves pickles just as much as she loves drama!

#11 – Ellen DeGeneres, Nicki Minaj

Can you hear that boom, boom-badoom? With 13 Emmys and 14 People’s Choice Awards, it’s no surprise that Ellen DeGeneres is one of the most talented comedians in Hollywood. First launching her career in the 1980s and quickly catching Johnny Carson’s eye, Ellen’s career skyrocketed. From having her own sitcom in the 1990s to joining the talk show circuit in 2003 with “The Ellen DeGeneres Show”, America quickly fell in love with the quirky dancing comedian.

But, dancing isn’t all that Ellen enjoys. With a knack for surprises, Ellen had more in store for her October 2013 audience than just a quick dance down the aisle when she revealed her Halloween costume. Typically dressed conservatively in slacks and a suit jacket, jaws dropped as Ellen came out on stage dressed like singer Niki Minaj. In an almost unrecognizable costume, Ellen truly bared it all with fake breasts, a fake butt, leather pants and a long blonde wig. Looks like even Ellen knows something about the Super Bass

#10 – Matt Lauer, Pamela Anderson

The second daytime television host on our list, Matt Lauer has been a television journalist with NBC’s “The Today Show” since 1997. With experience as a news anchor in New York City as well as a local talk show host and ESPN sideline reporter, Lauer’s experience has helped him establish his credibility as a trustworthy news source for many Americans. But, Lauer has also proven that he has a wicked sense of humor.

With morning news shows known for their shenanigans to lighten the early morning moods of their audiences, Lauer’s 2013 debut as Pamela Anderson on “Baywatch” shouldn’t have been all that surprising. But, it was and we really (really) wish we could erase it from memory! Dressed in full costume complete with a long blonde wig and fake breasts, Lauer was a good sport as he ran in typical “Baywatch” babe slow motion. If the sight of him in a bathing suit doesn’t get to you, knowing he had to use tape to keep everything in place should do the trick!

#9 – Chris Brown, Taliban

When isn’t Chris Brown in the news? Widely considered as one of the most controversial artists in history, it’s undeniable that Chris Brown is also one of the biggest stars in music. First starting out with hits like “Run It!”, Brown continues to release hit records despite his ongoing run-ins with the law. With a knack for finding trouble and welcoming drama with open arms, Brown’s 2012 Halloween costume was in poor taste even for him.

When Rihanna threw her Hollywood Halloween bash in 2012, she probably didn’t expect her ex to steal the show. Dressed as members of the Taliban, Brown and his crew shocked even their closest friends with their offensive costumes. Wearing head to toe Taliban gear with a fake beard and robe to even a chain of bullets, Brown quickly learned that people could in fact hate him even more.

#8 – LeAnn Rimes & Eddie Cibrian, White Trash

You can move the girl out of the country but you can’t take the country out of the girl! Hailing from Jackson, Mississippi, LeAnn Rimes first turned heads in country music at just 13 years old. With a voice resembling that of Patsy Cline, the teen became one of the youngest musical stars of all-time with hits like “Blue” and “How Do I Live”.

The now 33 year old country singer turned even more heads in 2011 but not for her heartfelt lyrics and killer voice. Alienating some of her country fan base, Rimes and husband, Eddie Cibrian, dressed up as a “White Trash’ couple complete with bad tattoos and camo. In true spirit of a Southern shotgun wedding, Rimes was a very pregnant bride with beer in hand as her husband, dressed in a cutoff tux and white washed jeans, held her baby bump. Though we can’t help but give them an A+ for execution, we can only imagine that some of her Southern fans noticed the uncanny resemblance.

#7 – Lucy Hale, Jagicorn

Moving to Los Angeles at 15 years old with the hopes of landing a record deal, Lucy Hale finally caught her big break as one of five winners on “American Juniors”, a spin-off of “American Idol”. With an obvious on-stage presence and likability, it didn’t take long before ABC Family cast the young hopeful as Aria Montgomery on the hit series “Pretty Little Liars”.

Even with a busy schedule filled with taping the series and recording an album, Hale still manages to enjoy the small things, even Halloween. Following similar fashion to Taylor Swift’s Pegacorn costume earlier on our list, Hale proudly debuted her Jagicorn costume in 2013. Though we aren’t quite sure what the mix is, our best guess is that Hale meant to look like a pink jaguar and unicorn. Aside from the footie pajamas, this costume is a definite fail as it looks more like a tragic ending for a lonely pajama party.

#6 – Tom Brady & Gisele Bundchen, The Cowardly Lion & Dorothy

Just stick to throwing touchdowns, Brady! When people ask, “Who’s the greatest NFL quarterback of all time?”, to most, the answer seems obvious: Tom Brady. With four Super Bowl wins, there’s not much to argue with as the New England Patriot has earned his fame by setting countless records and leading his team to incredible victories on the field.

So when fans heard that Brady wanted to be a lion, Detroit couldn’t help but get excited. Unfortunately for them, it was all for nothing. Dressed as the Cowardly Lion in 2013 with his wife, supermodel Gisele Bundchen, as Dorothy, the couple earned a collective and heartfelt “aw” from fans as they had yet another reason to love their favorite quarterback. Go ahead and calm down, Detroit, there’s no chance this lion is cowardly enough to leave New England.

#5 – Kate Upton, Skeleton Marilyn Monroe

Easily one of the most recognizable models in the world, Kate Upton gained notoriety in 2011 after her first appearance in the Sports Illustrated Swimsuit Issue. Named Rookie of the Year as a result, Upton has since been the cover model for the 2012 and 2013 issues and has graced countless other covers including Vanity Fair, all while trying her hand at acting.

With her blonde hair and flawless beauty, Upton has often been compared to Marilyn Monroe, which inspired her 2012 costume. Obviously with a flair for the dramatic, Upton revealed her modern fright-night version of Monroe, skeleton and all. Tiptoeing between life and death, Upton’s portrayal of Monroe was complete with the iconic white dress, red lips and curly hair but proved to be extra scary with skeleton makeup on her arms and legs. It looks like this Marilyn might’ve come straight from the grave!

#4 – Jason Biggs, Dorothy

“There’s no place like home!” Gaining instant notoriety for his infamous love…of…pie in the 1990s hit American Pie, Jason Biggs has found ongoing success in Hollywood. Most recently known as the voice of Leonardo in Nickelodeon’s “Teenage Mutant Ninja Turtles”, Biggs has also starred in “Orange is the New Black” and The Wizard of Oz…ok, so maybe not!

If you thought Tom Brady looked silly as the Cowardly Lion, then think again! Dressed up as Dorothy for a Halloween party in 2005, Biggs took crossdressing to an entirely new level. Wearing a blue checkered dress and long pigtails, Biggs bared his hairy legs and even carried around Toto in a picnic basket. Though we’re impressed with his dedication to the character, we’re a bit disappointed that he didn’t wear real ruby red slippers! Maybe next time!

#3 – Heidi Klum

We’ve already met one cover girl from the Sports Illustrated Swimsuit Issue, so why not meet another? German model Heidi Klum is not only a frequent cover-feature model, she’s also a Victoria’s Secret Angel and host on “Germany’s Next Top Model” and “Project Runway”. Yet, somehow Klum manages to make time for her favorite holiday, Halloween.

Klum could actually have her own wing in the Hall of Fame for Oddest and Strangest Halloween Costumes. Each year, Klum hosts one of the biggest Halloween parties and invites all of her celebrity friends. Not wanting to be outdone by her guests, the pressure is always on for Klum. For her 2015 bash, the model dressed as Chupacabra, an Indian goddess who looks more like a female Transformer. Possibly the weirdest of Klum’s costumes, the supermodel is unrecognizable in what must have been the strangest costume of the night!

#2 – Perez Hilton, Miley Cyrus

Another celebrity guest to Heidi Klum’s annual Halloween Party, Perez Hilton is the only person on our list who became famous from blogging. Starting PageSixSixSix.com, Hilton made a name for himself after featuring photos of celebrities with his own doodles and snarky comments. Despite being one of the most loved and hated personalities in Hollywood, the big name in the entertainment news world still gets invited to even the hottest Halloween bashes.

Did we mention Hilton loves to make snarky comments? In 2013 when Miley Cyrus was all the rage, countless people parodied the artist by dressing up as her for Halloween. Among those was Hilton who walked the red carpet at Klum’s party in full Cyrus costume. Complete with a latex bra and underwear, Hilton bared his hairy legs and completed the famous look from MTV’s Video Music Awards with red lipstick and fangs. While we’re impressed with the look, we definitely didn’t need a Cyrus repeat!

#1 – Julianne Hough, Crazy Eyes

Didn’t you know that orange is the new black? At just 27 years old, Julianne Hough got her first taste of fame after being partnered with Apolo Anton Ohno on the fourth season of “Dancing with the Stars”, which the pair won. Since then, Hough has continued to dance while also pursuing a career in acting with roles in films like Footloose and Rock of Ages.

Having recently returned to “Dancing with the Stars” as a judge, Hough has proven to be controversial both on and off the dance floor. With quite possibly the worst celebrity costume ever, Hough dressed as Crazy Eyes from “Orange is the New Black” for a Halloween party in 2013. While the idea itself isn’t bad, Hough offended many as she wore blackface to complete the costume. Thankfully for Hough, the real Crazy Eyes, Uzo Aduba, wasn’t all that worried and said, “I think maybe it was an unfortunate event, but she apologized and I feel like we can all move on.” But please, no more blackface, Julianne!