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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