If anyone has the resources to pull off a truly great Halloween look, it’s a Hollywood star. They’ve got access to skilled tailors, the best makeup artists in the world, and the money to spend on fantastic props (or set wardrobes to raid). In many cases, they’ve been on set with some of the very characters many of us ordinary people choose to emulate. With all of that in mind, though, it’s remarkable just how many A-listers have managed to get Halloween so wrong.
A brief investigation of the world of terrible celebrity costumes shows that most blunders fall into one of few categories; when they’re not culturally appropriating or being accused of racism, they’re out of touch with real world issues, or simply a tad cringe. We’d also add an honourable mention for all the times, for reasons unbeknownst to the general population, that they’ve dressed up as food.
From The Rock’s ill-fitting lion’s mane to Snooki’s love of the pickle, here’s a ranking of the worst celebrity Halloween looks of all time.
20. Hugh Grant
The award for the world’s laziest costume is easily won by Hugh Grant’s appearance at UNICEF’s annual Halloween Ball in 2015. Grant is one of the most successful British stars of our time, famed for his charisma and romcom-hero style, but you wouldn’t think so judging by this ill-fitting onesie and bizarre shaggy hood. At least he looks happy.
19. Paris Hilton
“In the real world, Halloween is when kids dress up in costumes and beg for candy. In Girl World, Halloween is the one day a year when a girl can dress up like a total sl*t and no other girls can say anything else about it.” Cady Heron, 2004
18. Snooki
Snooki loves pickles so much that she became one. As far as pickle costumes go, we’re willing to defend this one on grounds of creative flair. The Jersey Shore star wore a dress made of what looked like sliced pickles at a Halloween party in Las Vegas in 2010, accessorised with a satin green cape.
To avoid confusion, she also carried a massive gold spear with a pickle on top. Snooki later tweeted that she chose the costume hoping someone would give her a free pickle subscription. We admire the hustle.
17. Katy Perry
Hot Cheetos have consistently been hailed as the USA’s favourite snack. According to a recent a study, 77 million Americans consumed at least one bag of the crisps in 2020. Whether this information makes Katy Perry’s 2014 costume any more palatable is yet to be determined. Bonus points, though, for the matching shoes.
16. Kyle MacLachlan
Sticking with the theme of dressing up as food items, Kyle MacLachlan’s chose to dress up as kale for Halloween 2016. While the leafy vegetable has become somewhat of a “superfood” in recent years, sticking random bits of kale on your head and body is an insult to smoothie connoisseurs everywhere. The actor later revealed the costume referenced director David Lynch’s nickname for him.
15. The Rock
Mufasa is turning in his grave at this abomination. We’re yet to see a celebrity take on the lion costume and succeed. The Rock is out of the running with this poor attempt from 2020, which looks like it was bought from a children’s section.
14. Scott Disick
That time Scott Disick dressed up as an Arab Sheikh. “Happy halloween! We getting Arab money tonight,” he wrote on Instagram.
13. Tia Mowry
The actor caused an uproar in 2013 when she shared an Instagram post of herself wearing extremely fair makeup and dressed up as a Japanese geisha.
12. Princess Beatrice
The only royal here, Princess Beatrice earns a spot on the worst dressed list for this bizarre and lacklustre costume from 2016.
We’d argue that no one over the age of 10 should be dressed up as a unicorn for Halloween, but if you are so inclined, a purple wig and plastic headpiece is hardly sufficient.
11. Ashley Benson
Pretty Little Liars actor Ashley Benson sparked controversy in 2015 when she shared a now-deleted photograph on social media of herself wearing a “Cecil the Lion” costume.
Cecil was a male African lion who was lured out of a protected area in the Hwange National Park in Zimbabwe and killed by Walter Palmer, an American trophy hunter.
10. Ashley Tisdale
The High School Musical star was criticised for wearing face makeup reminiscient of skull decorations displayed on Día de los Muertos, a Mexican celebration that pays tribute to deceased loves ones.
Tisdale paired the skull makeup with a sheer black top, which her critics said “sexualised” the holiday.
9. Taylor Swift
“Can’t talk right now, I’m doin hot squirrel s***.” Though famed for leaving countless easter eggs for her fans, Swift sadly left no hidden messages in this Halloween look from 2021. She’s literally just dressed like a squirrel.
8. Katy Perry and Orlando Bloom
Katy Perry and Orlando Bloom are often hailed as “couple goals”, but this matching look from 2021 – a doctor and the Covid-19 vaccine – left fans divided. Some cringed at Bloom’s “Dr Dilf” ID badge, while others praised the pair for raising awareness around the vaccine drive.
7. Chrissy Teigen
The list of celebrities who have worn Native American headdresses on Halloween is long. Chrissy Teigen wore the look in 2008, and later told Sports Illustrated she was both her favourite, and most regrettable costume.
“The best costume I ever wore was actually something I forced John to wear,” Teigen said. “I made him a cowboy and I was an Indian, so we were ‘cowboys and Indians.’ It was, to me, very cute, but now thinking back I’d never do it again. Bad idea, Chrissy, bad idea!”
6. Ellie Goulding
The singer dressed up as a Native American in 2014. She responded to criticism on Twitter, writing: “I wore that beautiful unauthentic headpiece for about 5 minutes.”
5. Hilary Duff and Jason Walsh
The Lizzi McGuire star and her personal trainer boyfriend made headlines in 2016 when they attended a Halloween party in Beverly Hills dressed as a pilgrim and Native American.
In an apology shared to Twitter, Duff wrote: “I am SO sorry to people I offended with my costume.It was not properly thought through and I am truly, from the bottom of my [heart] sorry.”
4. Heidi Klum
When it comes to Halloween, no celebrity is quite as revered for dressing-up as Heidi Klum. We’ve seen various show-stopping tributes over the years, from her take on Shrek’s Fiona in 2018 to Jessica Rabbit in 2015. Unfortunately, Klum badly missed the mark and faced widespread criticism in 2008 when she opted to dress up as Kali, the Hindu goddess of death and time.
3. Julianne Hough
A number of Hollywood stars have worn blackface makeup to dress up as Black characters and celebrities; Julianne Hough on Halloween 2013 when she dressed up as Orange Is the New Black’s Crazy Eyes, Jimmy Kimmel when he dressed up as basketball player Karl Malone in 1999, and Jason Aldean, when he dressed up as Lil Wayne in 2015.
2. Jason Aldean
A photograph shared by Nashville Gab in 2015 showed Jason Aldean dressed up as Lil Wayne and wearing blackface makeup on Halloween.
The singer later defended the costume, telling Billboard that people are “so sensitive that no matter what you do, somebody is going to make a big deal out of it”.
“Me doing that had zero malicious intent … I get that race is a touchy subject, but not everybody is that way. Media tends to make a big deal out of things. If that was disrespectful to anyone, I by all means apologise. That was never my intention. It never crossed my mind.”
1. Harry Hamlin
Harry Hamlin faced fierce backlash in 2015 when he wore a T-shirt bearing the Nazi swastika as part of his Halloween costume. Hamlin and his wife, Lisa Rinna, dressed up as Sex Pistol’s star Sid Vicious and his girlfriend, Nancy.
