As far back as the history of image-making goes, the rich and famous have been commissioning great artists to capture their likeness. If you were a nineteenth century society beauty trying to impress your friends, you probably would've called upon a portraitist like John Singer Sargent to paint you in quiet repose. Now, if you're a celebrity or an influencer gunning for It-girl status in the digital age, you're likely spending at least part of every year planning an elaborate Halloween photo shoot with a professional photographer like Amber Asaly, Greg Swales, Jacob Webster, or Edwig Henson.
To be clear, I'm not talking about the obligatory photos celebrities take on the step-and-repeat outside Heidi Klum's annual Halloween bash, or the candids they snap with their kids before trick or treating. I'm talking about the Halloween glamour shots they book to showcase especially transformational looks—many of which are custom, designer, and intended to come off just as soon as they go on.
Henson has been dreaming up eye-popping Halloween costume shoots with "Have Mercy" singer Chlöe Bailey since 2021, when his renderings of Bailey as Betty Boop and Lola from Shark Tale racked up more than a million likes each.
"It's almost like a competition to top yourself and see who can do it best," Henson says of the trend. "All the celebrities gotta pop out or it's not giving. I know it's all a friendly game, but the girls really go in on this."
Like so many trends, the celebrity Halloween photo shoot tradition seems to have originated with Kim Kardashian. And more specifically, her 2019 triple-costume turn as Elle Woods from Legally Blonde, Betty Rubble from The Flintstones, and a giant glow-worm. Hailey Bieber's annual Halloween portraits, which she's been taking with Asaly since 2020, have seen her shape-shift into Britney Spears, Carmen Electra from Scream, and Cady Heron from Mean Girls.
For Jacob Webster, shooting Doja Cat's Halloween costume portraits in 2021 led to becoming her full-time photographer today—a "breakthrough" for his career. He's since expanded his Halloween portfolio to include the likes of Megan Fox in costume as Pamela Anderson, Keke Palmer as the Bride of Frankenstein, and Saweetie as Y2K Baby Phat ad-era Kimora Lee Simmons.
"From working with various artists, I've noticed Halloween is a time for them to step outside their usual roles," Webster explains. "It’s a chance to let loose and have fun in ways they might not be able to in their professional lives. Many celebrities use Halloween to experiment with ideas they've always wanted to try or to pay homage to iconic pop culture moments that shaped them as artists."
Many celebrities use Halloween to experiment with ideas they've always wanted to try or to pay homage to iconic pop culture moments that shaped them as artists.
Webster initially noticed a spike in demand for Halloween shoots after pandemic restrictions on party-going challenged celebrities to commemorate the holiday in a different way. The reason they've stuck around is more nuanced.
In a world where aesthetics across both beauty and fashion are being flattened at every turn, Halloween offers a rare chance for celebrities to exercise total creative autonomy. And what they do with that freedom feels more telling—and strangely, more real—than any red carpet look ever has.
Maybe, at their core, the most beautiful women in Hollywood just want to be worms and bugs for a night.
