But 20 years before Kendall Jenner, Florence Pugh, and their ilk normalized these “naked outfits,” another style icon was paving the way for the risqué aesthetic: Britney Spears.

In the early aughts, Spears hadn’t yet been legally defined by a conservatorship — that started in 2008 — so she had agency over her outfits, with creative input from the designer duo Kurt Swanson and Bart Mueller, AKA Kurt and Bart.

In her new memoir, The Woman In Me, she writes, “I never knew how to play the game. I didn’t know how to present myself on any level. I was a bad dresser — hell, I’m still a bad dresser.”

So with Kurt and Bart’s help, the princess of pop experimented with unusual looks in the early aughts. Many of those have become today’s ubiquitous trends, such as exposed lingerie and sheer dresses — and this was in a less welcoming, more controversial environment.

Her signature look from the decade was the divisive whale tail, which has had a 2023 revival as well. Spears did it early and often.

Continue scrolling for six of Britney Spears’ most risqué outfits from the early 2000s. Much like her music, her fashion choices often stand the test of time.

A Bedazzled, Built-In Whale TailKMazur/WireImage/Getty ImagesJeff Kravitz/FilmMagic, Inc/Getty Images

At the 2000 MTV Video Music Awards, Spears wowed the crowd with a mashup of “Oops!… I Did It Again” and the Rolling Stones’ “Satisfaction.” Her outfit was nearly as memorable.

She started the performance in a black bedazzled pantsuit, which she ripped off to reveal a saucier look underneath: a crystal-encrusted bra with matching flesh-tone, low-rise pants. The sheer bottoms came equipped with a built-in whale tail, marking one of the first of many exposed thong looks she’d wear.

See-Through Lace & Visible UndiesKMazur/WireImage/Getty Images

The following year, Spears returned to the award show in similarly revealing outfits. First, on the red carpet, she rocked a see-through mini dress made of black lace, featuring a peekaboo black bra and underwear. (Over a decade later, she recreated the look at the 2016 Billboard Music Awards.)

The exposed undies look has seen a resurgence in 2023, with celebs like Dua Lipa, Beyoncé, and Gwyneth Paltrow testing out the racy style.

A Bra & A Live SnakeFrank Micelotta Archive/Getty Images Entertainment/Getty Images

She swapped out the lace dress for a skin-forward performance outfit, which would cement her in pop culture history.

To sing “I’m A Slave 4 U,” Spears wore a green bra and barely-there bedazzled shorts, and she upped the ante with her accessory: an albino Burmese python named Banana. Because what’s more risqué than using a real snake as a scarf?

Spears considers this one of her all-time “favorite” performances, but as she recalls in The Woman In Me, it was also “terrifying.” She writes, “All I knew was to look down, because I felt if I looked up and caught its eye, it would kill me.”

A Peekaboo Whale TailJim Smeal/Ron Galella Collection/Getty ImagesJim Smeal/Ron Galella Collection/Getty Images

In 2001, Spears joined her then-beau Justin Timberlake at a launch party for *NSYNC’s Celebrity album. She may have been a guest, but sartorially she stole the show, pairing a teeny corset with dangerously low-rise jeans. The real star of her look, however, was the beige G-string poking out from her pants — a major 2000’s whale tail moment.

An Exposed Thong MomentKMazur/WireImage/Getty Images

In 2003, Spears performed for MTV TRL’s Brand Spankin New Music Week in a look that’d be used 20 years later as inspiration for the return of low-rise pants.

She wore a long-sleeved cropped shirt with brown leather pants, which featured a V-shaped waistband that dipped past her undies. The metallic purple G-string was a fitting accessory for the cacophony of the venue: Times Square.

Free The NippleFrazer Harrison/Getty Images Entertainment/Getty Images

Even though freeing the nipple has “wound people up” in 2023, according to Florence Pugh, the trend dates back to at least the 1940s. Even so, it hasn’t always been socially acceptable.

In 2003, the singer sported the look at an event at Utah’s Sundance Film Festival. She wore low-rise, flared pants with hip cut-outs — classic Spears — with her pièce de résistance: an off-the-shoulder, see-through top.

22 Years Ago, Britney Spears Rocked A Whale Tail At An *NSYNC Party

With Julia Fox, Kim Kardashian, and Dua Lipa as ambassadors, the whale tail’s controversial comeback is showing no signs of slowing down. And there’s one person to thank for catapulting the trend into existence in the first place: Britney Spears.

Back in the early aughts, few stars were bold enough to rock the whale tail; even fewer dared to wear it repeatedly. The “Toxic” singer, however, was a trailblazer who donned the look several times. (Oops!…She did it again.)

Spears made the risqué, undies-flaunting style her signature look in the 2000s, sporting it on stage, at events, and at one of her then-boyfriend Justin Timberlake’s parties.

Britney’s Glam/Grunge Look

In 2001, when Spears and the former boy band member were still a couple, she attended the launch party of Celebrity, *NSYNC’s fourth studio album. At the West Hollywood event, Spears outfitted herself in her signature saucy outfit combo: a tiny top and dangerously low jeans.

On top, the pop princess wore a deconstructed corset crafted from bits of silver and gray fabric. The front featured exaggerated criss-crotch stitching that added to the intentionally haphazard effect.

Jim Smeal/Ron Galella Collection/Getty Images

Meanwhile, Spears donned purplish-gray leggings that hung extremely low on her hips. Like silhouettes of yore, the fitted low-risers flared out at the bottom. On brand with the undone look, her pants were equipped with ruffles and exposed seams.

A Red Carpet Whale Tail

It wasn’t until the Crossroads actress turned around that the star of her ensemble was revealed: her champagne-colored thong. The slinky undies peered out of her pants in infamous Y2K whale tail fashion.

Jim Smeal/Ron Galella Collection/Getty ImagesBritney’s Bedazzled Belly Button Ring

Spears’ crop-top-and-low-rise combo left her waist utterly bare. The “Toxic” singer utilized the real estate by accessorizing spicily, as she is wont to do.

She wore a bedazzled belly button ring with a diamond-encrusted star that dangled past her navel. The nostalgic piercing was another detail that captured the essence of the ’00s. (And much like the whale tail, it’s also making a comeback.)

Jim Smeal/Ron Galella Collection/Getty Images

Elsewhere, she accessorized with equally glitzy pieces, including a pair of skinny earrings, a crystal-encrusted choker, and a bracelet-slash-ring combo.

Iconic.