Miley Cyrus Looks Back on Her Infamous VMAs Teddy Bear Costume: 'Made a Lot of People Angry'

"The bear reminded me of myself for some reason, I thought it was beautiful," the singer revealed in British Vogue's Life in Looks video series

Miley Cyrus is looking back at the most fashionable — and in some cases, controversial – style moments of her life.

The singer, 30, took a trip down memory lane for British Vogue's Life in Looks video series, proudly remembering some of her greatest fashion hits.

Cyrus began with an outfit from her Hannah Montana era before turning the page and seeing a photo from a performance in a club in Paris in 2010.

"I have 250 individual hair extensions," she said, seemingly still amazed before turning her attention to her outfit. "I wore this because I felt like it was protective and I also felt like it was a complete difference from Hannah Montana's style," she explained.

"This was my way of expressing myself as Miley and introducing myself as Miley to the world," Cyrus continued. "I had been a character for so long, so this was the beginning of, like, developing who Miley would be."

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Next, the "Wrecking Ball" singer turned to her infamous teddy bear costume from MTV's 2013 VMAs. Looking directly at the camera, Cyrus said the costume "was extremely controversial and made a lot of people angry. I repeat, this teddy bear costume made a lot of people angry."

She went on to explain how the ensemble came together. "This was inspired by a Todd James sculpture that I had fallen in love with. The bear reminded me of myself for some reason, I thought it was beautiful."

"I had my own custom bear by Todd James made for me that I could be inside of and be birthed [at the beginning of her performance], which was what was happening, it was a rebirth," Cyrus said.

The multi-hyphenate also chatted about her "Mother Daughter" music video that starred her mom, Tish Cyrus.

"We are both in Chanel. Me and my mom love to match. I know that's something you're supposed to outgrow, but I haven't," she said with a laugh.

She continued: "My mom is the most sexy, most powerful, most strong, smartest woman in the entire world that I know. We both are very inspired by her mom. My grandmother was a 'Glamazon.' "

One of the last photos she talked about was a two-piece chain ensemble she wore for 2021's Miley's New Year's Eve Party on NBC, in which she famously suffered a wardrobe malfunction.

"This outfit did not stay on very long because the chain in the back broke," she revealed, "but what is a live TV performance with everything going right?"

"Live TV is a tightrope walk. They wanna see you dangle, but they don't wanna see you fall. We had promoted the show as, 'It's Miley Cyrus and Pete Davidson. They're so wild. You never know what's gonna happen,' and comparably to Pete, I'm pretty classy, and the ratings were skyrocketing," she remembered, throwing her hands in the air.

"Show your boobs and you get renewed. Dolly taught me that," she said while laughing, referring to legendary country singer (and her godmother!) Dolly Parton.

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