Kylie Jenner and Her BFF Were Madonna and Britney Spears for Halloween

From Harper's BAZAAR

  • Kylie Jenner dressed up as a Madonna while her best friend Anastasia Karanikolaou dressed up as Britney Spears at the 2003 VMAs, where the two pop stars kissed onstage.

  • Jenner recreated Madonna's all-black outfit with a top hat, microphone, and blonde wig.


Years after she famously dressed up as Christina Aguilera, Kylie Jenner honored another pop icon this Halloween: Madonna. To make the tribute even sweeter, Jenner's best friend Anastasia "Stassie" Karanikolaou dressed up as Britney Spears, and the pair recreated the singers' looks—and performance—from the 2003 VMAs.

{% verbatim %}

View this post on Instagram

Britney and Madonna

A post shared by Kylie Jenner News (@kyliesnapchat) on Oct 27, 2019 at 12:48am PDT

{% endverbatim %}

At the infamous '03 award show, Madonna, Britney, and Christina Aguilera took the stage together for a steamy, wedding-themed performance of "Like a Virgin" and "Hollywood." The set ended with Madonna making out with both of her costars onstage—an iconic moment in pop culture history.

Photo credit: J. Shearer - Getty Images
Photo credit: J. Shearer - Getty Images

Jenner and Karanikolaou nailed their looks as their respective pop personas this weekend. The beauty mogul donned Madonna's all-black outfit and even wore a blonde wig and darkened her eyebrows to look identical to the singer. Meanwhile, Stassie copied Britney's lacy white outfit, with coordinating boots and gloves. The BFFs carried microphones while dancing and lip syncing to "Like a Virgin" in their costumes, and sealed the impromptu performance with a quick kiss.

Some of Kylie's recent Halloween costumes include a pink butterfly (she matched with her daughter Stormi) , a skeleton, a Victoria's Secret Angel, and a literal angel. Back at home this weekend, Stormi Webster paid tribute to her mother by wearing a mini version fo Jenner's Met Gala outfit this year.

You Might Also Like