Christina Aguilera's Y2K style rebellion still influences fashion decades later, and with Halloween in full swing, what better time to revisit her most daring wardrobe moments and trace her evolution from '90s pop princess to unapologetic rocker chic?
Some of her most iconic looks continue to be a hit for Halloween, especially among celebrities. Who can forget Halloween 2016 when Kylie Jenner famously recreated Christina's ensemble from her 2002 "Dirrty" music video, a red-and-white striped bikini top, red-and-black-highlighted hair extensions, and red leather chaps?
In 2024, Christina opened up to Glamour about the narrative surrounding her body during the height of her fame.
"When you’re a teenager, you have a very different body than when you’re in your 20s," she said. "I started to fill out, and then that was unacceptable because it was like, 'Oh, she’s getting thicker.' Then I had industry people: 'They liked your body and how you were as a skinny teenager.'"
She continued: "I have a maturity now where I just don't give a [expletive] about your opinion. I'm not going to take it on. It must be your responsibility to take up your space. Other people's opinions of me are not my business."
"Your kids trigger things in you that you don't want them to go through. And it’s almost like you're reliving this whole thing again," she added.
From her 2002 MTV Video Music Awards look to her Versace corset dress, HELLO! takes a closer look at the singer's most daring looks from the height of her fame.
© AFP via Getty Images2000 ALMA Awards
Her daring looks began early in her career.
In 2000, Xtina wore a shimmery pale-pink dress with strappy sandals to the 2000 ALMA Awards, but it was the hip-high slit that got everyone talking.
© Ron Galella Collection via Getty2001 Grammy Awards
In true Y2K style, Xtina wore a semi-sheer knit dress to the 2001 Grammy Awards that highlighted her body.
The look was completed with blonde braids for a daring finish.
© Getty Images2002 MTV Video Music Awards
One of her most iconic looks, for the 2002 MTV Video Music Awards Christina rocked a tiny denim skirt and a scarf styled as a top that showed off her toned abs.
In classic Y2K fashion, she added a white pageboy hat to the look.
© Corbis via Getty Images2004 Grammys
By 2004, gone were the textured braids, with Christina switching things up with dark black hair.
For the Grammys, she wore a plunging asymmetrical pink dress with a deep and wide set neckline, accenting her toned shoulders.
© Patrick McMullan via Getty Image2006 MTV Video Music Awards
It was another new look two years later, as the singer channeled Marilyn Monroe with a glitzy gown and Old Hollywood updo at the 2006 MTV Video Music Awards.
© Gareth Cattermole/Getty ImagesVersace dress
For the opening night of Burlesque: The Musical in 2026, Christina rewore an archival green Versace gown, 22 years after she first modeled it for a campaign.
The dress, with a sweetheart strapless neckline, visible corsetry, and asymmetrical hemline, remains daring, decades on.
