Cringiest Celebrity Halloween Costumes, Ranked main image
Scroll Down To Continue

Cringiest Celebrity Halloween Costumes, Ranked

We all do it at one time or another. We pick out a Halloween costume that we just know will be epic. We plan for weeks in glee just waiting for the reactions we know we'll get. And then we get to the party and realize that our costume just falls flat once we're out in public. Sometimes it's just a misunderstood costume that needs too much explanation. And then sometimes, the costume needs no explanation at all, but an apology for how offensive it truly is. As embarrassing as it is for us, just imagine how it must be for celebrities.

They literally have cameras following them around everywhere, and when they mess up, it makes the front page of all the tabloids in American. Depending on the severity, it could reach the front page of magazines and websites all over the world

You would think, in the day and age of all things internet, celebrities would just know better. However, as you can see from this list, there were at least 30 times that celebrities made the wrong costume choices and ultimately had to make public apologies for them. Here are the cringiest celebrity costumes ranked from the cringy to the cringiest of all time.

33. Perez Hilton – Miley Cyrus

33. Perez Hilton – Miley Cyrus

Perez Hilton has never shied away from controversy. He’s always wanted to remain smack-dab in the middle of it all, which was why he went as Miley Cyrus for Halloween during one of Heidi Klum’s infamous parties. They’re all the rage, and Perez had tons of pics taken with him in this outfit.

It doesn’t help that Perez Hilton seems to constantly jab at Miley, resurfacing (or releasing) photos of her. One was even a photoshop that supposedly showed her crotch when she was getting out of a car. Yeah, he should probably just leave the young woman alone, right?  

Andrew H. Walker/Shutterfly/Getty Images

32. Mark Wright - Tekashi 6ix9ine

32. Mark Wright - Tekashi 6ix9ine

Mark Wright faced a ton of backlash in 2021 when he posed as rapper Tekashi 6ix9ine for Halloween. This comes only a few years after Tekashi was charged in 2015 for the use of a child in a sexual performance. Wright claimed the Halloween costume was inspired by his 2020 video "Goomba," but that doesn't mean it isn't in poor taste. 

Soon after the backlash started, Wright disabled comments on his photo, which was captioned "Happy Halloween" while tagging 6ix9ine in the photo. Now, he deleted it, but the internet doesn't forget. Later, he apologized for the photo and costume altogether. 

(Image via Instagram)

31. Steve-O — Sasquatch

31. Steve-O — Sasquatch

The Jackass actor posted this photo on Twitter with the caption, "Thanks so much to about 100 dudes who donated their pubes to my epic Halloween costume! Sasquatch lives!!! Woohoo!!!"

...if we were wearing other people's pubes, not so sure we'd be that excited. But to each their own, Steve-O.

(image via Twitter)

30. Katy Perry & Orlando Bloom — Vaccine & Dr. DILF

30. Katy Perry & Orlando Bloom — Vaccine & Dr. DILF

If anyone wondered where Katy Perry and her husband Orlando Bloom stood on the whole vaccine debate, they made it pretty clear on Halloween 2021. The couple dressed up as "Dr. DILF" and a "Katy & Perry" vaccine. Fan reactions were mixed.

Some loved the couple's costume and commented things like, "RELATIONSHIP GOALS" on Perry's Instagram post. Some, however, were skeptical about the inspiration behind the costume. Some questioned whether Bloom was really dressed up as "Dr. DILF" or the now-controversial figure Dr. Fauci. One user commented, "Wow how much money did you get paid for this? Lmao."

(Image via Instagram)

29. Megan Fox and Machine Gun Kelly – Obviously Church-Goers

29. Megan Fox and Machine Gun Kelly – Obviously Church-Goers

Megan Fox and Machine Gun Kelly are once again showing the world that they are the cringest couple out there. The pair had two costumes, but this costume is so cringe that it's hard to even look at it. Maybe the funniest part is that people really chewed them up. One person said, "They're unbearable now." 

The caption read, "On Sundays we take communion." Naturally, this sent everyone into a tizzy in the comment section, saying that the costume was disrespectful because it was mocking someone's religion. We'll just leave you with the wise words of another commenter..."Girl....get up."

(Image via Instagram)

28. Kelly Osbourne - Rachel Dolezal

28. Kelly Osbourne - Rachel Dolezal

Overall, this was just a bad decision. Rachel Dolezal by herself is offensive. She was an equal rights activist who presented herself as a black woman despite the fact that she was born to two white parents. Being that she's pretty controversial, Kelly Osbourne dressing as her for Halloween landed her in some hot water. 

It doesn't help that a week prior to that, Kelly Osbourne posted a photo of Dolezal when she was younger (with very light skin and blonde hair) next to Dolezal today. This meant that Osbourne knew what Dolezal was doing, but decided to throw on a curly wig and call it "#CallMeRcahel"

(Image via Instagram)

27. Ashley Benson – Cecil the Lion

27. Ashley Benson – Cecil the Lion

Flashback to Halloween 2015 and the uproar (pun definitely intended) was over Ashley Benson’s idea of a funny costume. When the actress posted a photo of her wearing a sexy lion costume, her original caption made a reference to the lion that had recently made headlines for being slain on protected grounds.

After several users let her know that they thought her costume idea was offensive, the Pretty Little Liars star changed the caption to just say lion. She later defended herself by saying she only wore the costume for a few minutes and took it back off.

(Image via Instagram)

26. Kylie Jenner – Eskimo

26. Kylie Jenner – Eskimo

I mean. Are we surprised that yet another Kardashian has appeared on this list? On Halloween of 2015 Kylie Jenner posted a photo of herself dressed up on Insta with the caption “Eskimo.”

She later changed it to say “Snow Princess” after she came under fire for her offensive remark, but many were not buying it. The term Eskimo is generally considered a slur, and fans did not appreciate her using it.

(Image via Instagram)

25. Gwen Stefani – Harajuku

25. Gwen Stefani – Harajuku

This one may seem like a stretch, but it really isn't (and we'll tell you why). Back in the early 2000s, Gwen Stefani went through a phase when she loved Asian culture, specifically Harajuku culture. That being said, she went a little overboard with it, turning real live people into dolls. That's why she's on this list, as she used them as part of a costume. 

Even the women, who were later dubbed Love, Angel, Music, Baby, admitted that Stefani didn't treat them with respect and that they felt more like part of a costume that fetishized their culture. For that reason, we're putting her on this list. That being said, she also dressed up in Harajuku attire, so she just overall crossed the line. 

James Devaney/WireImage/Getty Images

24. The Chainsmokers – “Ebrola”

24. The Chainsmokers – “Ebrola”

Okay, so this one wasn’t Halloween either, but it’s pretty offensive. During the 2014 Ebola pandemic the EDM-pop duo, The Chainsmokers, dressed up as “Ebrola” health care workers while playing at a frat house.

The epidemic at that point had so far claimed more than 5,000 lives and was nothing to sneer at. However, these guys found a way to turn it into a joke and never apologized.

(Image via Youtube)

23. O.J. Simpson – Gynecologist

23. O.J. Simpson – Gynecologist

Okay, so maybe this one isn’t so much controversial as just in bad taste. O.J. Simpson, formal football super-star-turned-con, is most commonly known now for having killed his wife and her lover and for the most part got away with it.

The ex-con dressed as a gynecologist named Dr. Seymour Bush. But instead of being offended by the costume, bar guests lined up for selfies and autographs.

(Image via Instagram)

22. Rihanna - Pot

22. Rihanna - Pot

Well, this isn't the worst on the list, but it certainly earned Rihanna her share of backlash. For Halloween, she went scantily clad and dressed up as marijuana. Parents who let their kids listen to Rihanna were certainly shocked, but we can't help but wonder if they should limit what their kids listen to if they have such a problem with it. 

It isn't exactly like Rihanna's music is kid-friendly. This one comes to us from 2012, but Ri-Ri didn't leave it there. Recently, in 2021, she dressed up in a "joint dress" for the 30th Anniversary of Dazed magazine. We get it, but now it's getting to be a little on the nose, right?

(Image via Instagram)

21. Ashley Tisdale – Sugar Skull

21. Ashley Tisdale – Sugar Skull

This one is still debatable. In 2016, when High School Musical alum, Ashley Tisdale, attended gal pal Vanessa Hudgens's Halloween bash dressed up as a sugar skull, the Internet was set on fire immediately.

Many were angry at the actress for cultural appropriation. Still, many defended the actress, stating that it was considered a costume in Mexican culture as well.

(Image via Instagram)

20. Kate Hudson - Wild Wild Country Cult

20. Kate Hudson - Wild Wild Country Cult

Kate Hudson got some major backlash after she dressed up for Halloween as the Rajneeshees. It is a cult that was featured in the Netflix documentary, Wild Wild Country. She posted the Instagram picture with the caption from the cult's leader, "Don't be worried about the future. Live this moment so totally that the next moment comes out of it golden."

As you can imagine, people weren't a fan. Critics accused Hudson of being insensitive and noted that the cult has committed several crimes over the years, including poisoning local townspeople. Emulating a group that's committed bio-terrorism just isn't okay, Kate. Then, quoting the man as if he was a good person? That's gonna be a no from us. 

(Image via Instagram)

19. Jeff Ross – Joe Paterno and Company

19. Jeff Ross – Joe Paterno and Company

Okay so this wasn’t for Halloween, but it’s pretty controversial. Jeff Ross showed up to Roseanne Barr’s comedy roast dressed as Jerry Sandusky—or more commonly known to Penn State fans as JoePa—with two boys dressed in nothing but towels and football helmets.

The comedian, who admitted his costume was controversial, claimed that he was making a statement. We think the statement may have been lost, here.

Gregg DeGuire/WireImage/Getty Images

18. Scott Disick – Sheik

18. Scott Disick – Sheik

In 2014, then honorary Kardashian, Scott Disick thought it would be fun to play Arab Sheik for Halloween. He posted a pic of himself in costume with the caption “We getting Arab money tonight.”

While many didn’t see any harm in the costume, there were many who were disappointed with the reality star’s choice of cultural appropriation. Disick never apologized for the costume, but eventually Khloe Kardashian did once she realized their faux pas.

(image via Instagram)

17. Kenya Moore - Native American "Warrior Princess"

17. Kenya Moore - Native American "Warrior Princess"

We're not sure what's worse about this one: the fact she did it at all or the fact it happened on TV. Kenya Moore, famous for her role in The Real Housewives of Atlanta, went on the show dressed as a "warrior princess." It was complete with a full outfit and a headdress. 

Later, after she was called out, she posted a Twitter post that stated, "I want to apologize for inappropriately wearing the Native American headdress as a costume. I now realize that this was both disrespectful and insensitive." Wait, she needed to be told that it was awful to do? 

(Image via Bravo)

16. Shaun White – Simple Jack

16. Shaun White – Simple Jack

In 2018, Olympic gold medalist, Shaun White, attended a Halloween party dressed as Simple Jack from the 2008 film Tropic Thunder. Almost immediately the Special Olympics blasted the Olympian for setting a bad example. They made a statement to Huffpost.com, “…Disability is not a joke, nor should it be a punchline…”

The three time Olympic champion apologized almost immediately. His response was, "I owe everyone in the Special Olympics community an apology for my poor choice of Halloween costume the other night," White said in a statement on social media. "It was a last minute decision. It was the wrong one. The Special Olympics are right to call me out on it."

(Image via Instagram)

15. Tia Mowry – Geisha

15. Tia Mowry – Geisha

In 2013, Tia Mowry decided to dress as a traditional Japanese Geisha for her Halloween party. Many of her Insta followers were not impressed. One user commented “My race and the races of others are not a costume for a cheesy holiday.”

Another commented, “Please do some research on cultural appropriation. Geisha costumes are not cool, girl.” However, the actress wasn’t daunted because she never removed the post nor apologized for it publicly.

(Image via Instagram)

14. Chrissy Teigen – Native American

14. Chrissy Teigen – Native American

In 2008, Chrissy Teigen and John Legend attended a Halloween party, Legend as a cowboy and Teigen in full Native American regalia. This immediately sparked outrage across the interwebs.

Although it sparked controversy, Teigen stated that, “It was, to me, very cute, but now thinking back I’d never do it again. Bad idea, Chrissy, bad idea!”

Michael Tullberg/Getty Images Entertainment/Getty Images

13. Hillary Duff and Jason Walsh - Native Americans

13. Hillary Duff and Jason Walsh - Native Americans

In 2016, actress Hilary Duff and then boyfriend, Jason Walsh, donned sexy matching Pilgrim and Indian costumes. Pretty insensitive at the time, considering that the North Dakota pipeline protests were growing more and more volatile.

They won the prize for being the first celebrities to apologize for a Halloween costume faux pas in 2016 considering they released their apologies on their separate Insta accounts on All Hallows Eve.

Michael Kovac/Getty Images Entertainment/Getty Images for Casamigos Tequila

12. Nicky Hilton – Native American

12. Nicky Hilton – Native American

Ummm. Like… Duh. Apparently big sister didn’t learn from little sister’s mistake from 2010 because in 2015, Nicky dressed up as a Native American at the 2015 Casamigos Halloween Party.

You would think that with the world becoming more multiculturally diverse and aware that celebrities (who are supposed to be role models) would be a little more sensitive to the subject.

Amy Graves/Getty Images Entertainment/Getty Images

11. Ellie Goulding – Native American Chief

11. Ellie Goulding – Native American Chief

In 2014, singer Ellie Goulding made a faux pas by not only dressing as a Native American, but also by posting a now deleted photo of herself on Instagram dressed up with the caption saying, “Chief.” She then posted a second now-deleted photo wearing a large tribal headpiece that included beading and feathers.

Her followers were quick to criticize the star and she quickly deleted the photos. She then defended herself, saying, “I only wore that beautiful unauthentic headpiece for about 5 minutes,” but then also agreed to donate to a Native American charity.

Christopher Polk/Getty Images Entertainment/Getty Images

10. Chris Hemsworth - Native American

10. Chris Hemsworth - Native American

Just days before Halloween in 2016, Chris Hemsworth shared his biggest costume faux pas — his Native American costume. This came during a post with Taika Watiti where he held a sign saying he "stands with those at Standing Rock." In the description of the post, he brought up when he attended a "New Year's Eve" party that was themed after the Lone Ranger.

He admitted, "I was stupidly unaware of the offence this may have caused and the sensitivity around this issue. I sincerely and unreservedly apologise to all First Nations people for this thoughtless action." At least he told everyone about it before we pulled it up from the dust. 

(Image via Instagram)

9. Heidi Klum – Goddess Kali

9. Heidi Klum – Goddess Kali

Super-model Heidi Klum has become sort of a Hollywood legend for her extensive and ornate Halloween costumes over the years. As a matter of fact, most of the time you can’t even tell who is behind the makeup or masks.

However, Heidi’s idea to dress up as the Goddess Kali fell flat as Hindus around the world took offense in 2008. Hmmm... Maybe it was the severed heads, or the knife-wielding that did it...

Joe Corrigan/Getty Images Entertainment/Getty Images

8. Bill Maher – Dead Steve Irwin

8. Bill Maher – Dead Steve Irwin

Just barely more than a month after Crocodile Hunter, Steve Irwin, was killed by a stingray while filming on the Great Barrier Reef, Bill Maher decided to shock the world by dressing up as Irwin.

While dressing up as the zoologist might not have made headlines, the fact that it was a bloody costume with a stingray tail sticking straight out of his chest. And what made it worse? The comedian refused to apologize for the costume because he figured Irwin may have “been doing something” to the stingray that he shouldn’t have been.

(Image via HBO)

7. Bill Murray – Jimi Hendrix

7. Bill Murray – Jimi Hendrix

In 2010, Bill Murray hosted the Crossroads Guitar Festival in Bridgeview, Illinois on June 26th, 2010. Unfortunately, he chose to show up dressed as Jimi Hendrix in full blackface.

Although this took place before celebs were shamed across social media, when the photo of Bill as Jimi did make it’s rounds on the interwebs, the backlash was minimal and many took it in the spirit in which Bill probably intended in the first place.

Kevin Mazure/WireImage/Getty Images

6. Chris Brown – Terrorist

6. Chris Brown – Terrorist

As if he didn’t have enough controversy in the media already at the time, in 2012, Chris Brown made headlines once again. This time it was for his choice of Halloween costume.

Brown and a bunch of his friends thought it would be cute to dress up as Muslim terrorists for Halloween in 2012. The internet did not agree.

(Image via Instagram)

5. Jason Aldean – Lil Wayne

5. Jason Aldean – Lil Wayne

In 2015, Jason Aldean dressed up as Lil Wayne, complete with blackface, dreadlocks, and bling and headed out on the town in Nashville with a group of friends. The Internet reacted swiftly and angrily.

Eleven months later, the country singer issued an apology that was not an apology at all. “In this day and age people are so sensitive that no matter what you do, somebody is going to make a big deal of it… If that was disrespectful to anyone, I by all means apologize.”

(Image via Twitter)

4. Colton Haynes – Kanye West and Mahatma Gandhi

4. Colton Haynes – Kanye West and Mahatma Gandhi

Colton Haynes of Teen Wolf fame has a long history of intricate Halloween costumes, sometimes they’re weird, sometimes they’re funny, and sometimes they’re just downright offensive.

In 2011, Haynes thought it would be cute to wear a long, gold chain, black sweat suit, and gold rimmed sunglasses, complete with blackface to dress as Kanye West. Then he turned around the next year and put on blackface again to dress up as Mahatma Gandhi! Celebs just never learn…

(Image via Instagram)

3. Jimmy Kimmel - Karl Malone

3. Jimmy Kimmel - Karl Malone

Comedians definitely risk crossing the line, but something like this should have been obviously bad. Jimmy Kimmel — yes, the late-night TV show host — once dressed up as famous basketball player Karl Malone during a skit on The Man Show. Even back then we knew that blackface was poor taste, so why did he do it?

We're sure that people threw out the excuse of "boys will be boys," but that's not really gonna fly here. Kimmel apologized for his skit, but he honestly never should have done it in the first place. That's just a line you don't cross comedically or otherwise. 

(Image via Comedy Central)

2. Macklemore - Um...This

2. Macklemore - Um...This

So the Jewish people aren't really unfamiliar with being treated awfully, but this? This has gone too far. Many Jewish fans have come out to criticize Macklemore for his anti-Semitic caricature. There's zero excuse for this move. Macklemore said he "chose the costume pieces at random" in an attempt to surprise fans.

Well, he certainly shocked a lot of his fans. There was no way that these pieces were chosen at random. We don' know if it was a joke gone badly or what, but Macklemore decided to defend his position. Although, eventually he did apologize for offending anyone. Just look in the mirror before walking out on stage, man. 

Suzi Pratt/FilmMagic/Getty Images

1. Julianne Hough – Suzanne “Crazy Eyes” Warren

1. Julianne Hough – Suzanne “Crazy Eyes” Warren

In 2013, Orange Is the New Black hit Netflix and the world had a new obsession. Apparently, Julianne Hough was also obsessed and decided to portray one of her favorite characters of the show for Halloween that year—complete with blackface makeup.

Another celeb who arrived at the party at the same time tried to get to Hough quickly to tell her to take off the blackface makeup before photos were taken, but alas, she was too late. The photos of the celeb in blackface quickly made the rounds on social media and Hough was forced to post a formal apology the next day.

(Image via Twitter)