Throughout the years, celebrities have tried to be crowned the best dressed of Halloween, yet few actually wore costumes that have stood the test of time.

From film characters to out-of-the-box creations, though, some musicians, actors and models went above and beyond, flexing their strengths as creatives. Their costumes portrayed various characters and concepts that broadcast their artistry, demanding eyes to be on them.

Troye Sivan as Addison Rae in the streets of Los Angeles pretending to read a book (2024)

This costume will only be understood by the chronically online. Troye Sivan’s niche look brought him a lot of attention when he recorded a TikTok with Charli xcx and Addison Rae.
Walking down the streets of L.A., Addison Rae was “reading” Britney Spears’ memoir “The Woman in Me.” The paparazzi caught her leaving a cafe in Beverly Hills and took pictures, begging the question: Was it candid or plan-did?

The Australian singer used his sense of humor and was able to create the perfect costume. His Rae look consisted of a braided wig, a cropped tank top, some short shorts and the final touch: Spears’ memoir. With every detail in place, Sivan was among the best-dressed for Halloween that year.

Cardi B as Marge Simpson (2022)

Back in 2022, Cardi B did multiple looks, including Marge Simpson from “The Simpsons” in her iconic outfit, but instead of a dress, it was a revealing corset. Painting herself all yellow, she went all out and even recreated the set of the animated sitcom from the opening credits. Cardi’s authenticity brought the costume home, paying homage to the character while adding a twist in her style. Her Marge was feminine with a touch of sexy that only Cardi B could bring.

Translating beloved TV and film characters from the screen to a costume often goes sideways because it can seem like a cheap copy, but Cardi B stamped her own brand into the beloved character.

Justin Timberlake as LEGO Robin (2018)

Dressing up as Robin from the “Batman” series is already an interesting choice, but Justin Timberlake thought outside the box, bringing his LEGO Robin costume to life. His costume featured a life-sized, accurate LEGO Robin figure with his red hair and the claw-like hands characteristic of the LEGO brand.

Timberlake was not alone in this endeavor, as his son dressed as LEGO Batman and wife, Jessica Biel, as LEGO Harley Quinn, adding to the dedication to the costumes. The three were photographed in New York City trick-or-treating, giving people a wholesome family moment.

Lizzo as a Dubai chocolate Labubu (2025)

TikTok’s term “brain rot” has become popular among Generation Alpha and Generation Z, referring to words or concepts that do not make sense in any context other than memes on the Internet.

Dubai chocolate Labubu is one of these concepts; while Dubai chocolate and Labubus exist, the combination of the two does not. Lizzo took it to the next level this year, combining the trendy objects into one brain rot term and giving the people what they want.

The songstress has been obsessed with Labubus, referencing them in one of her freestyles and performing with people dressed as them onstage. The devious-looking Labubus have become popular among collectors, so it is fun to see a big name like Lizzo source the toy as inspiration for her viral costume.

Heidi Klum as a worm (2022)

Saving the best for last, Heidi Klum constantly brings her A-game when it comes to Halloween to the point where People crowned her the “Halloween Queen.” Every year, she raises the bar as each costume tops the next, from a peacock to a futuristic alien. However, there is one that takes the cake: her 2022 worm costume.

Worn at her 21st annual Halloween bash, every minute detail of the costume felt impeccable, straight out of a horror film. The worm’s prosthetic designer, Michael Marino, has worked on multiple cinematic and television productions, most notably Colin Farrell’s penguin transformation in “The Penguin” and Sebastian Stan in “A Different Man” (2024).

Unmatched, Klum’s dedication to the holiday makes each year’s costume a performance, rather than just a simple outfit. Every year, publications run to see what Klum will do next — including the Daily Trojan — cementing her as the holiday’s ambassador. Will another celebrity surpass the queen of Halloween?