The Most Stylish Celeb Halloween Costumes of All Time

last updated 30 October 2025

I must admit that I'm not much of a Halloween person. I usually half-ass my costumes using pieces I already own mixed with cheap Party City accessories. (A striped shirt with a sailor hat has been my go-to costume for several years running.) After compiling this story, I'm feeling extra inspired this year to come up with something a bit more fun. The costumes I included below aren't scary, out-there, inventive, or silly—they're just plain stylish. They can be re-created with things you already own or items you can absolutely wear again post-Halloween.

Celebrities such as Margot Robbie and Lupita Nyong'o have worn excellent Halloween costumes over the years, and they deserve to be revisited. I also included throwback looks from Jane Birkin, Jamie Lee Curtis, and Cindy Crawford—you're welcome. Scroll down to see the most stylish Halloween costumes, according to me.

Jane Birkin as a Circus Performer

Jane Birkin dressed as a&nbsp;circus performer&nbsp;for Halloween.

Margot Robbie as Ginger Spice

Margot Robbie dressed as Ginger Spice for Halloween.

Sabrina Carpenter as Tinker Bell

Sabrina Carpenter dressed up in a Halloween costume

Emily Ratajkowski as Jennifer Lopez

Lupita Nyong'o as Dionne From Clueless

Lupita Nyong'o dressed as Dionne from Clueless for Halloween.

Cindy Crawford as Marilyn Monroe

Cindy Crawford dressed as Marilyn Monroe for Halloween.

Mindy Kaling as Elle Woods

Mindy Kaling dressed as Elle Woods from Legally Blonde on Halloween.

Jasmine Tookes as Foxxy Cleopatra

Jasmine Tookes dressed as Foxxy Cleopatra from Austin Powers for Halloween.

Olivia Rodrigo as Elvira Hancock

Olivia Rodrigo dressed as Elvira from Scarface for Halloween.

Jamie Lee Curtis as a Witch

Jamie Lee Curtis dressed as a witch for Halloween.

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Erin got her start as a Who What Wear intern in 2011—back when the site only published a single story per day. (We have since increased that number twentyfold.) She graduated magna cum laude from USC and lives in Los Angeles. In college, she also interned at Refinery29, where she was promoted to editorial assistant and then assistant editor. After nearly three years at R29, she came back to WWW in 2015, where she is now the Associate Director of Fashion News. From the Oscars to the Met Gala, she leads the site's entire red carpet coverage strategy. She specializes in celebrity and fashion news but also enjoys writing travel features and runway reports. She frequently contributes to WWW's social accounts and has a sizable following on her personal TikTok.