19 of the boldest Halloween costumes celebrities have ever worn

Katy Perry Cheat

Katy Perry will be seen at Kate Hudson’s annual Halloween party on October 30, 2014. Chinchilla / Bauer-Griffin / GC Images / Getty Images

  • Halloween is the perfect time for celebrities to abandon their glamorous style and wear something wild.

  • Over the years, stars like Paris Hilton and Kylie Jenner have chosen bold and clear looks.

  • Others like Rihanna went a different path and completely changed themselves.

  • For more articles, please visit the Insider homepage..

In 2003, Mariah Carey made a bold mermaid look at her Halloween party. Her outfit included a shell-shaped bra and a low-rise skirt with a wide slit in front.

Mariah Carey dressed as a mermaid at the Halloween party in October 2003.

Mariah Carey will attend her private Halloween party on October 31, 2003 in London. David Westing / Stringer / Getty Images

Demi Lovato was unrecognizable at his party ten years later. She wore a long-sleeved dress with a torn bottom, white face paint with dark make-up, and fake blood.

2013 Halloween Demi Lovato.

Demi Lovato at the Halloween Party in California on October 31, 2013. Christopher Pork / Getty Images

Rihanna abandoned her attractive style in 2014 to dress up as the Teenage Mutant Ninja Turtle. Her outfit included green face paint, metal bustiers and leather gloves.

Rihanna dressed as the Teenage Mutant Ninja Turtle at Halloween 2014.

Rihanna poses with her friends in New York City on October 31, 2014. NCP / Starmax / Getty Images

Katy Perry took a quirky route that year, dressed as a cheat. I wore a red bodysuit and matching sneakers under a snack-inspired costume.

Katy Perry Cheat

Katy Perry arrives at Kate Hudson’s Halloween party in California on October 30, 2014. Chinchilla / Bauer-Griffin / GC Images / Getty Images

At the 2015 Halloween party, Heidi Klum transformed into Jessica Rabbit. She wore a strapless red gown with bold slits, a prosthesis on her chest and face, purple latex gloves, and red pumps.

Heidi Klum dressed as Jessica Rabbit at Halloween 2015.

Heidi Klum at the Halloween Party held in New York City on October 31, 2015. Nicholas Hunt / Getty Images

At the same party, Emily Ratajkowski dressed as Marge Simpson. But instead of wearing a yellow dress under a green minidress, she painted her whole body from head to toe.

Emily Ratajkowski at the 2015 Heidi Klum Halloween Party.

Emily Ratajkowski at Heidi Klum’s Halloween Party on October 31, 2015 in New York. Andrew Toss / Getty Images

Kylie Jenner looked exactly like Christina Aguilera in 2015, dressed in a costume inspired by the 2002 “Dirty” music video. She paired a striped bikini top with red shorts and leather chaps. Jenner also wore a blonde wig with black stripes.

Kylie Jenner dressed as Christina Aguilera at Halloween 2016.
Kylie Jenner dressed as Christina Aguilera on Halloween 2015. Splash news

Winnie Harlow channeled RuPaul in 2018 wearing a red latex corset-style leotard. She also wore thigh-high boots, a blonde hairstyle, and a black fur coat.

Winnie Harlow dressed as RuPaul for Halloween 2018.

Winnie Harlow will pose in New York City on October 31, 2018. Gilbert Crow Squilo / Getty Images

At another party that year, Kendall Jenner dressed as a Fembot in the “Austin Powers” series. She wore a blonde wig, pink gloves, and feathered heels in a see-through babydoll dress.

Kendall Jenner 2018 Halloween

Kendall Jenner at the Halloween Party in Las Vegas on October 31, 2018. Brian Stephy / Stringer / Getty Images

Jessica Biel and Justin Timberlake wore cubic outfits transformed into Harley Quinn and Robin Lego to trick or treat their children.

Jessica Biel and Justin Timberlake for Halloween 2018.

October 31, 2018, Jessica Biel and Justin Timberlake in New York City. Robert Camau / Getty Images

Frankie Grande appeared unrecognizable that year when dressed in silver paint and brilliance to dress as the “Troll” franchise Guy Diamond. He also wore a metal wig, a green nose, and platform shoes.

Frankie Grande dressed as a troll at Heidi Klum's 2018 Halloween party.

Frankie Grande at a party held in New York City on October 31, 2018. Taylor Hill / Getty Images

In 2019, Khloé Kardashian added a bold twist to the classic Cruella de Vil costume. She wore a black-and-white dress with huge shoulder pads, a plunged neckline, and thigh-high slits.

Chloe Kardashian Cruella Costume


Bella Hadid wore a bikini version of Fred Flintstone that year. She also added bone-shaped earrings and a dark pixie haircut.

Bella Hadid dressed as Fred Flintstone for Halloween in 2019.

Ashley Graham wore a maternity version of the Jessica Rabbit costume. Her appearance included a red wig, purple gloves, and a strapless latex gown with thigh-high slits.

Ashley Graham dressed as Jessica Rabbit for Halloween in 2019.

Jordyn Wood and Megan Thee Stallion wore a crucifix bikini in 2019 in costumes inspired by Tekken and Street Fighter. Woods added fishnet tights to her look and Megan wore thigh-high boots.

Jordyn Woods and Megan Thee Stallion dressed up for Halloween.

In 2020, Bella Thorne dressed as Little Red Riding Hood. Her costume included a red cloak, thigh-high tights, and a latex mini dress with a wide open chest.

Bella Thorne dressed as the 2020 Halloween Red Riding Hood.

Paris Hilton added a twist to the classic nurse costume of the year and wore a white dress with a deep square neckline. It also included a snug skirt, pointed pumps, and Chanel gloves.

Paris Hilton dressed as a nurse on Halloween 2020.

Paris Hilton will be dressed as a nurse on October 31, 2020 in Los Angeles, California. Mega / Getty Images

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