All of Britney Spears's Most Underrated Y2K Looks

There’s no doubt that Britney Spears’s style is the stuff of pop culture legend: the bright red catsuit from Oops. . . I Did It Again, the schoolgirl outfit in . . . Baby One More Time, Toxic’s blue flight attendant ensemble. Each has launched a million Halloween costumes, perhaps the ultimate barometer for whether someone’s style is emblazoned on pop culture iconography.

The list of Spears’s legendary looks, whether on the stage, in a video, or on the red carpet (never forget the matching denim-on-denim with JT) is endless. What’s less talked about is how Spears popularized a number of trends that now define Y2K style, like the bubblegum vibrancy of the color palette and bedazzled, glitter-strewn embellishments.

What’s unique to Spears are the elements of ’70s boho style that wove their way into many of her looks, although always with a Y2K spin. The early 2000s saw Spears in crop tops with bell sleeves, baby tees worn under shearling coats, low-rise flare jeans, and fringe pieces in multicolor hues. There was something about Britney’s happy-go-lucky, unpretentious style that made it appealing, and its vibrant youthfulness always retained a sense of fun that never took itself too seriously.

Ahead, we’ll review some of Spears’s more underrated looks that further cement her as one of the great style icons of the past 20 years.

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We could never say to no to a neon moment, particularly when paired with a patterned miniskirt.

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Yes she dared to rock the crop top with a low-rise skirt, as she should.

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(Image credit: Dave Hogan/Getty Images)

Sequined top? Check. Sequined pants? Check.

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The sleeves, the buttons, the color… this top is total Y2K eye candy.

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These long, fur-trimmed cardigan-coats need to make a comeback. And yes, we see the butterfly boots.

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(Image credit: Chris Weeks/Getty Images)

Boldly taking orange where few dare to tread.

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LBD, but make it quintessentially Britney Spears.

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(Image credit: Kevin Mazur/Getty Images)

Black-tie glamour from Ms. Spears.

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Snakeskin pants in aqua blue? Don’t mind if we do.

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(Image credit: Ron Wolfson/Getty Images)

Deep cowl necklines are a repeated motif in Spears’s 2000s looks.

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(Image credit: Barry King/Getty Images)

The purple fringe, the teal necklace—we love it all.

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(Image credit: Dave Hogan/Getty Images)

A more pared-back moment for early-2000s Britney.

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This fuschia color is so stunning, but the beading takes it to the next level.

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(Image credit: Kevin Mazur/Getty Images)

The halter neckline, layered chain belt, and acid-wash flare jeans make this the outfit of our preteen dreams.

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(Image credit: Lalo Yasky/Getty Images)

We could never say no to a corset dress. This gorgeous lacy-blue number with the floral shawl is perfection.

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(Image credit: Dave Benett/Getty Images)

Spears turns the bedazzled meter up to ten.

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The corset top trend had a huge moment in the early 2000s.

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There’s just something about the pink-on-pink with the cargo pants.

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Those boots! Spears ventured into neutrals more than expected in the 2000s.

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The pageboy cap and dress-over-jeans combo is too nostalgic.

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You don’t need to layer when the coat speaks for itself.

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The sheer organza jacket is such a whimsical detail. Side note, who didn’t love Spears's short bob moment around 2000.

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Tracksuit, but dress it up. The orange shades are also a must.

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Sabrina Paparella