Dating back to the history of portraiture, the rich and famous have commissioned great artists to paint their portraits. If you were a 19th century socialite trying to impress your friends, you probably commissioned a portrait painter like John Singer Sargent to paint you in quiet repose. Now, if you are a celebrity or influencer aspiring to It Girl status in the digital age, you probably spend at least part of each year planning an elaborate Halloween photo shoot with a professional photographer like Amber Assaly, Greg Swales, Jacob Webster, or Edwig Henson. You'll probably spend at least part of it.

To be clear, I'm not talking about the obligatory step-and-repeat photos celebrities take outside Heidi Klum's annual Halloween party or the candy photos they take with their kids before trick-or-treating. I'm talking about the Halloween glamour shots that are specifically reserved for showing off a transformed look, many of which are custom designer-made and intended to be taken off as soon as they are put on.

Henson has been dreaming up eye-popping Halloween costume shoots with “Have Mercy” vocalist Chloe Bailey since 2021, and his depictions of Bailey as Betty Boop and Lola from “Shark Tale” each received over one million “likes” on the site.

“It's like a competition to see who can do it best,” Henson says of the trend. 'If all the celebrities don't pop up, it's not given. I know it's all a friendly game, but the girls really get into this."

”It's a lot of fun.

Like many trends, the celebrity Halloween photo shoot tradition seems to have started with Kim Kardashian. More specifically, she dressed up as Elle Woods from Legally Blonde, Betty Rubble from The Flintstones, and a giant glow worm in 2019. Hailey Bieber has transformed into Britney Spears, Carmen Electra from Scream, and Cady Heron from Mean Girls in Halloween portraits that she has taken with Asari every year since 2020.

For Jacob Webster, it was shooting Doja Cat's Halloween costume portraits in 2021 that led him to become her full-time photographer today. Since then he has expanded his Halloween portfolio to include Megan Fox dressed as Pamela Anderson, Keke Palmer as the Bride of Frankenstein, and Saweetie as Kimora Lee Simmons from the Y2K Baby Phat advertising days.

“In working with various artists, I realized that Halloween was a time for them to step out of their usual roles,” Webster explains. It's a chance for them to be free to have fun in a way they wouldn't be able to in their professional lives,” Webster explains. Many celebrities use Halloween to try out ideas they have always wanted to try or to pay homage to iconic pop culture moments that shaped them as artists”

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Webster initially noticed a surge in demand for Halloween photography when celebrities took on the challenge of commemorating Halloween in a different way, as party attendance became more restricted. The reasons for their establishment are more subtle.

In a world where both beauty and fashion aesthetics are flattened at every turn, Halloween offers a rare opportunity for celebrities to exercise complete creative autonomy. And what they do with that freedom says more and, strangely, feels more real than any red carpet look.

Perhaps the most beautiful women in Hollywood just want to bug out for the night.