Britney Spears' 25 Most Iconic Fashion Moments

Britney Spears' 25 Most Iconic Fashion Moments

From newsboy caps and low-slung jeans to sheer catsuits embellished with rhinestones, Britney Spears has blessed us with some of the most memorable looks in fashion history. Whether posing on the red carpet, performing onstage, or dancing in a music video, Britney Spears always exudes confidence and sex appeal, and her style choices are similarly edgy, provocative, and boundary pushing.

On the heels of her return to the MTV Video Music Awards stage after a nine-year hiatus, take a look back at some of the most unforgettable outfits the Princess of Pop has rocked through the years. It's Britney, b**ch!


Image via FeatureFlash/Shutterstock

  • Flesh-Toned Number at the 2000 MTV VMAs


    When Britney opened the 2000 MTV Video Music Awards, audiences found her straddling a chair in a sequin-adorned black blazer and slacks paired with a white button-down blouse and a black fedora. As she sang the Rolling Stones' "Satisfaction," Brit rose from her chair and walked across the stage, eventually diving into her "Oops ... I Did It Again" hit. In one fell swoop, she shed her drab "business" clothes, revealing a risqué and totally ravishing nude-toned bra and matching low-slung pants ensemble adorned with sparkly rhinestones. She did it again!

  • Flight Attendant Flyness in 2001's "Toxic" Video


    A photo posted by Billboard (@billboard) on

    Audiences were totally on board with Britney Spears's flight attendant getup in 2004's "Toxic" music video. A sexy riff on the 1960s Pan Am stewardess uniforms, Brit's blue minidress featured a cleavage-flaunting center cutout, silver piping along the neckline and cinched-in waist, and a capelet with structured wing sleeves. The matching hat was the perfect finishing touch, making the outfit fly high through the friendly skies.

  • Biker Babe at the 2002 MTV VMAs


    A photo posted by Billboard (@billboard) on

    A year after mesmerizing us with her snake-assisted "Slave 4 U" performance at the Video Music Awards, Britney had a leather and lace moment at the awards show. Her biker-inspired ensemble consisted of a sleeveless, figure-hugging, button-up leather vest top; a stretchy mini skirt with a sheer side panel; elbow-length, black lace, finger-less gloves; a leather hat; and knee-high caged stiletto heels. Talk about finding a theme and going full throttle with it!

  • Schoolgirl Outfit in "...Baby One More Time" Video

    Image via YouTube/BritneySpearsVEVO

    Britney played into every man's naughty schoolgirl fantasy in her debut video, "...Baby One More Time." Wearing a pleated plaid skirt, knee-high socks, a white-button down tied into a knot (to reveal her toned midriff, of course), and a gray cardigan, she swayed her hips in between rows of lockers while giving the camera her most lustful looks. The pink ribbons and pom-pom accessories in her two braids completed the Lolita-esque look.

    More from CafeMom: Kim Kardashian's 9 Most Ridiculously Boob-Tastic Outfits

  • Ringmaster Jacket for the 2009 'Circus' Tour


    A photo posted by Billboard (@billboard) on

    Brit was the world's sexiest ringmaster during her worldwide "Circus" tour. Night after night, the Princess of Pop took to the stage in black fishnet tights, black knee-high lace-up boots, black leather micro shorts, and a red ringmaster jacket designed by Dan and Dean Caten of DSQUARED and featuring a tailcoat, gold braided details, royal blue cuffs, and fur-trimmed shoulders. Forget Barnum & Bailey: This was the greatest show on Earth!

  • Head-to-Toe Denim at the 2001 VMAs


    Back when Justin Timberlake and Britney Spears were pop's reigning power couple, they showed up at the 2001 MTV Video Music Awards in matching all-denim ensembles. For her part, Brit rocked a floor-length, strapless denim dress and accessorized with a low-slung, silver-toned chain-link belt, a wide choker necklace filled with shimmering gemstones, and a bejeweled denim frame purse. The outfit became so iconic that Katy Perry strolled down the red carpet at the 2014 VMAs in a similar jean dress ensemble, with rapper Riff Raff playing the Justin to her Britney. Imitation is the sincerest form of flattery, right?

  • Rainbow Hair at the 2015 Teen Choice Awards


    Britney Spears dressed the part when she picked up her Candie's Style Icon award at the 2015 Teen Choice Awards. Wearing a silver Mikael D dress with a plunging neckline, side cutouts, short cap sleeves, and a high-low hemline, the Princess of Pop sparkled on her big night. The green-and-purple tips of her hair, meanwhile, added just the right amount of pizzazz and attitude to the look. 

  • Gothic Romance at the 2016 Billboard Music Awards Red Carpet


    Though her stage outfit at the 2016 Billboard Music Awards stole the show, Britney made jaws drop on the red carpet when she showed up in this black lace Reem Accra number. The sheer long sleeves, high neckline, micro romper-style shorts, crocheted bodice, and long sheer train all created a vampy, dramatic, and undeniably sexy look. The knee-high, caged, peep-toe boots, meanwhile, added a fun S&M element to the outfit.

    More from CafeMom: 16 Revealng Red Carpet Looks That Made Jaws Drop

  • Glamorous in White at the 2000 Grammy Awards

    Image via Splash News

    One of the most iconic Marilyn Monroe fashion moments involved her exiting a limousine in a white satin column gown, elbow-length gloves, and a white fox fur stole. Madonna gave Monroe's famous look her own spin in 1991, when she arrived at the Grammys arm-in-arm with Michael Jackson. In 2000, it was Britney's turn to channel old Hollywood glamour as she walked the red carpet in a simple white halter dress with a white fur stole.

  • Sporty & Spunky at the 2001 Superbowl


    A photo posted by Billboard (@billboard) on

    When she joined Aerosmith onstage at the 2001 Superbowl Half-Time Show, Britney looked ready to party like a rock star, wearing a cleavage-flaunting, midriff-baring Aerosmith band T-shirt, sporty football-inspired white pants with a lace-up front and vertical side stripes, and a tube sock that had been transformed into an arm warmer.

  • Underwear as Outerwear in the "I'm a Slave 4 U" Video

    Image via YouTube/BritneySpearsVEVO

    Low-rise jeans were barely a phenomenon until 2001, when Britney started wearing them everywhere — including in her sweaty, super sultry "I'm A Slave 4 U" video. What better way to show off her perfectly toned midriff than with a fuchsia wrap-around bustier crop top and the most low-slung jeans ever made? But the real shock factor came from the pink panties she wore over her jeans, kickstarting yet another wave of the underwear-as-outerwear trend. 

  • Sexy Tuxedo Dress at the 2013 iHeartRadio Music Awards


    Britney turned the 2013 iHeartRadioAwards into a black-tie event (sort of!) when she showed up in a black tuxedo dress by Olcay Gulsen. But this was no ordinary penguin suit! Brit's tuxedo jacket dress featured an ultra-short hemline, no sleeves, and a plunging neckline that allowed her to reveal the lacy black bra underneath her frock. Ever the trend-setter, Brit predicted that chokers would make a major comeback and accessorized her dress with a black velvet ribbon choker necklace.

    More from CafeMom: 19 of the Most Shocking Red Carpet Looks Ever

  • Red Latex Catsuit in the "Oops, I Did It Again" video


    Black Widow and Storm may have looked great in their superhero jumpsuits, but they couldn't quite reach the heights of fashion greatness achieved by Britney Spears — or actor Kevin Bacon — in a red latex catsuit. Bacon famously wore a similar catsuit from Britney's "Oops! ... I Did It Again" video for an Apple Music ad that co-starred Britney, which shows just how iconic that outfit has become.

  • Newsboy Hat Moment at the 'Crossroads' Premiere

    Image via Splash News

    Britney wore a lot of newsboy caps in 2002 — a lot! Perhaps her most memorable cap-flaunting moment was when she attended the premiere of her film Crossroads with then-beau Justin Timberlake, a beige leather newsboy hat matching her shirred pink tunic top and pink high-heeled suede boots.