Kylie Jenner and BFF Stassi Karanikolaou Recreate Iconic Britney Spears and Madonna VMAs Kiss in Epic Halloween Costumes

Kylie Jenner and BFF Stassi Karanikolaou Recreate Iconic Britney Spears and Madonna VMAs Kiss in Epic Halloween Costumes
Kylie Jenner and Stassi Karanikolaou Shutterstock (2)


Who wore it better? Kylie Jenner and her best friend, Anastasia “Stassie” Karanikolaou, recreated Britney Spears and Madonna‘s iconic looks at the 2003 MTV Music Video Awards for their Halloween costumes.

Jenner, 22, shared a video of herself and Karanikolaou, 22, on her Instagram Story sporting their ensembles after a J Balvin concert in Los Angeles on Saturday, October 26.

The Keeping Up With the Kardashians star transformed into the Queen of Pop with a blonde wig tucked back into a bun and an all-black outfit. Meanwhile, Karanikolaou channeled Spears with a white corset top, white skirt and matching gloves.

Kylie Jenner and BFF Stassi Karanikolaou Recreate Iconic Britney Spears and Madonna VMAs Kiss in Epic Halloween Costumes
Stassi Karanikolaou and Kylie Jenner Courtesy of Kylie Jenner/Instagram

In the video, the pals dance along to Madonna’s “Like a Virgin” before going in for a quick peck on the lips — a tribute to Spears and Madonna’s headline-making kiss on stage at the VMAs.

Earlier that day, Jenner teased her costume in a video clip of the Kylie Cosmetics CEO listening to Spears’ 2007 hit “Piece of Me.”

This isn’t the first time Jenner has paid homage to an early 2000s pop culture moment. In 2016, she dressed as Christina Aguilera during her “Dirrty” era.

Britney Spears and Madonna VMAs Kiss
Britney Spears, left, and Madonna kiss during the opening performance of the MTV Video Music Awards at New York’s Radio City Music Hall on August 28, 2001. Julie Jacobson/AP/Shutterstock

The makeup mogul has been all about the fun following her recent split from Travis Scott. Jenner attended Drake‘s 33rd mobster-themed birthday bash on Wednesday, October 23. A source told Us Weekly that she was “never too far away” from the rapper at the event.

“She spent the most time near Drake and his friends,” a source told Us.“Kylie was rapping to songs and dancing with her friends while she was next to Drake, but they weren’t dancing together, they seemed to have a connection though.”

A second source told Us, “They seemed to be enjoying each other’s company. They were joking around and Kylie was laughing. She seemed to be really happy and in a great mood and her and Drake seemed very comfortable with each other. There seemed to be an attraction there.”

Earlier this month, Jenner became a viral sensation when a clip of her singing “rise and shine” to her 20-month-old daughter, Stormi, took over the Internet. Celebrities such as Miley Cyrus, Ariana Grande and Cody Simpson got in on the fun with their renditions of the lyric. Jenner even created merch with the phrase, which she put up for sale in her Kylie Shop.

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