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.

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

Layer this under neutrals to bring in a fun burst of color.

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

You can never have too many ribbed sweaters, and this one looks so comfortable.

Sequined top? Check. Sequined pants? Check.

Cowl necks have seen a resurgence, and we completely understand why.

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

Spears's outfits often incorporated fun nods to Western style. This suede belt is a chic way to channel the look.

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

This style comes in all sorts of fun colorways, including a metallic blue.

Boldly taking orange where few dare to tread.

Embrace bold color. These stretch flare pants come in multiple lengths, too.

LBD, but make it quintessentially Britney Spears.

Black-tie glamour from Ms. Spears.

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

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

The metallic detailing on this is so subtle and gives such a pretty sheen.

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

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

The halter neckline and side cutouts give this a subtle Y2K feel.

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

The tie-details on the straps, the wrap skirt—everything about this dress is stunning.

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

The slight wide legs on these are so chic.

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

So many Miaou corsets to covet, so little time.

Spears turns the bedazzled meter up to ten.

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

We love how Spears mixed jeans with a formal look—we think these jeans do something similar.

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

Because you can never have too many pockets.

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

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

You can't have a Spears-inspired shopping roundup without a pageboy cap.

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

This coat adds an instant cool-factor to any outfit.

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

This comes in every color imaginable and we want them all.

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

These just need a crystal butterfly on the lens and we'd be right back in 2003.

Up next, these are the Y2K fashion trends we're still wearing.

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