Britney Spears' Most Iconic Y2K Looks

Britney Spears may have become famous for her unforgettable pop anthems and her generation-defining dance moves, but her fashion is a considerable part of her legacy. It's been about two decades since Spears' heyday, but as an ultimate icon of Y2K fashion, young people are still trying to emulate her looks — especially now that the 2000s are back.

So what made Spears such a fashion icon? Well, she was never afraid to go big and bold with her looks, both on and off stage. It was Spears who helped usher in the crop top craze. She was also responsible for helping make low-rise bootcut jeans look like the pinnacle of high fashion. We have her to thank for butterfly clips, pale blue eyeshadow, fedoras, belts, and Y2K maximalism. As one of her designers, Alina Campbell, once told Page Six, "These looks, the belly shirts in particular, defined an era — an era that Britney ruled." As the undisputed queen of Y2K, we think it's high time we revisited some of her most memorable, history-making looks — here are Spears' best Y2K looks.

Shiny, hot pink tube-style crop top? Check. Low-rise white cargo pants — with knee pads? Check. High pigtails and shimmery makeup? Check and check! This unforgettable look from Britney Spears' 1999 "...Baby One More Time" tour (via Vogue) screams Millenium fashion, and we are utterly obsessed — and it seems that we aren't the only ones who remembered the look.

In 2021, pop sensation Ariana Grande recreated Spears' famous look while appearing as a judge on "The Voice" during the hit singing competition's '90s night. Thankfully, Grande gave us an excellent blueprint for how to update this look for many years to come. Instead of platform sneakers, Grande opted for white Giambattista Valli platform boots and paired the look with her signature high ponytail rather than Spears' iconic '90s pigtails (via Popsugar). Grande has totally inspired us to try this bold Y2K look for ourselves!

In 2000, Britney Spears showed up at the Billboard Music Awards in a genuinely unforgettable outfit (via Wonderwall). The pop star wore a long orange and purple lingerie-style jacket over a matching short set. As if this bold look wasn't enough, she paired it with maroon suede boots with pointed toes and a bright orange hat with purple details. She also wore purple fishnets and, of course, a large choker. With its many colors and materials, this look is the epitome of Y2K maximalism — and we are kind of obsessed.

However, there was a time when Spears wasn't such a big fan of the look. When asked about her "biggest fashion mistake" by Harper's Bazaar ten years after the event, she was quick to name this outfit. "I actually thought I looked hot at the time. But, um, I definitely stood out," she said. "I thought it was just a marvelous idea to wear this purple and orange outfit; it was like high school colors. I was a cheerleader for a school I didn't know. People were talking about it, but not in a good way."

Love it or hate it, this look is iconic. In fact, her jacket and shorts even went on auction in 2008 for $3,000 (via Gotta Have Rock and Roll).

When Britney Spears performed a medley of "(I Can't Get No) Satisfaction" by The Rolling Stones and "Oops!... I Did It Again" at the 2000 VMAs (via YouTube), her outfit became a key part of the show. She began the performance by wearing a black suit and matching fedora. Then, partway through the song, she ripped off the suit to reveal a barely-there rhinestone embellished two-piece consisting of a bedazzled bra and low-rise trousers.

Designers Kurt and Bart designed the infamous outfit along with David Dalrymple. Dalrymple shared on daviddalrymple.com that he believed the outfit was a "pivotal career moment" for him and Spears. And, as Billboard has noted, the outfit and performance marked a real turning point in her image, taking her from girl-next-door to global pop icon.

While you probably won't be imitating this outfit any time soon, this look has to be one of Spears' most iconic for Y2K fashion.

It would be impossible to discuss Britney Spears' impact on Y2K fashion without getting into her myriad crop tops. She was, after all, the queen of midriff-baring — and one of her greatest crop top moments took place at a 2000 Teen Vogue party (via Popsugar). The star wore a black lace-up crop top paired with a pair of incredibly shiny bright blue snakeskin print pants. With her sleek blonde bob and pale blue eyeshadow, this look had to be one of Spears' most memorable.

Even though Spears debuted the snakeskin trousers over 20 years ago, it seems that her influence is still playing a big part in fashion today. In 2018, Asos proclaimed that snakeskin pants were officially back in fashion thanks to designers like Isabel Marant. And in 2020, Bella Hadid wore a pair of bright yellow snakeskin trousers that were a total throwback to Spears' look (via The Zoe Report). Once again, it seems that Spears continues to be a huge trendsetter.

While Britney Spears may have become famous for her laid-back crop tops and low-rise jeans look when she hit the red carpet, she knew how to dress up. Her 2000 Grammys look has gone down in history as one of the most memorable red carpet moments of all time (via Fashionista).

"Britney brought a stunning '90s Marilyn moment to the Grammys this particular year with the platinum blonde hair and white gown, matched perfectly with the Oscar de la Renta scarf," 77S Studio's stylist Hannah Edge told The List. "It was elegant, classy, and the perfect gown for entering a new millennium."

Spears continues to make an impact with this all-white outfit. In fact, in 2020, R&B star Lizzo wore a white gown with a white fur wrap that was a clear homage to the pop star (via Harper's Bazaar). This Grammys outfit is undoubtedly one of the most iconic looks Spears ever gave us.

This ensemble has to be one of Britney Spears' most legendary looks of all time. During Spears' 2001 VMA performance of "I'm a Slave 4 U," the wily pop princess wore an unforgettable gauzy green fabric bra that wrapped around her torso. She paired the eye-popping bra top with a set of blue bedazzled booty shorts that featured draped fabric, feathers, and shiny trinkets, which dangled from her hips. She coupled her loosely tousled hair with a live snake as if this bold outfit wasn't enough. As snake handler Michael Hano later told Today, "At first she was scared and uncomfortable with it, but she pushed herself with it and did really well, I gotta say."

In 2017, this famous outfit, along with a few others, was put up for auction at a staggering $50,400 bid on eBay (via Footwear News). If that's not iconic, what is?

Britney Spears once again made fashion history at the 2001 MTV VMAs — this time, with a high-end navy blue mini lace dress courtesy of designers Dolce & Gabbana. While Spears opted to skip her signature crop top with this look, she did choose to wear only a set of matching navy blue underwear underneath. 

Clearly, the dress has served as inspiration for other stars over the years. In 2012, Mel B (aka Scary Spice) made headlines for wearing the same dress on a night out in London (via Daily Mail). And in 2021, Kourtney Kardashian also recreated the famous look, this time pairing it with black lace fishnets (via Page Six). It's apparent that we weren't the only ones who were hooked on this lacy, see-through look — which seems to resurface on the hottest celebrities and entertainers every 10 years or so!

One of Britney Spears' most iconic music video outfits came from her video for "Overprotected (Darkchild Remix)." In the video, Spears took aim at the media's constant criticism of her risque clothing by proudly wearing a gorgeous see-through lace green crop top over a pink bra and paired it with pink shorts and matching knee-high boots.

"Of all the things I created for Britney, this is by far my favorite," said designer Alina Campbell in an interview with Page Six. "I actually met Britney in person for this one. Kurt and Bart had me stop by her dance rehearsals for the video — which, by the way, was an incredible thing to see in person — and she tried the top on right after. It was lacy, sheer, had big slitted sleeves and was originally white."

Campbell explained that designers Kurt and Bart suggested it should be green. "Even when it was white, though, I could tell Britney loved the top and was excited to wear it," Campbell added.

While Britney Spears may be the unofficial Queen of the Crop Top, she also knew how to branch out with less revealing looks. For instance, one of the pop singer's greatest Y2K looks came in the form of a jumpsuit that she wore to the 2000 American Music Awards. The jaw-dropping grey jumpsuit featured full-length trousers, a rhinestone-lined halter neck, and a very, very deep cowl neck that dropped all the way down to her belly button.

At the time, Spears was still relatively new to the pop music scene. In fact, she ended up winning the award for "Favorite pop/rock new artist" that year. But, as Wonderwall pointed out, this mature, sexy outfit was the perfect way to introduce herself as a grown-up star — and a future fashion icon. She would only go on to wow her fans more as the years went by.

In addition to her era-defining fashion on the red carpet and on stage, Spears was also a fashion icon on the screen — particularly in her film "Crossroads." One of the most iconic pieces? Her "Crossroads" bucket hat. As Vogue U.K. noted, it was the perfect finishing touch for her character's sweet all-American vibe.

"Being a Britney fan myself from a child, 'Crossroads' is one movie that I loved and still love," Edge told The List. "The iconic bucket hat was an inspiration into my wardrobe in the early 00s, and almost every outfit I would style together, a bucket hat was always set as the perfect accessory. But as fashion recycles itself, bucket hats are still a staple on any summer trip for a casual beach day." That's right — according to a professional stylist, you can imitate this look today and still look like the height of fashion!

While Y2K darling Britney Spears began her career channeling sweet, girl-next-door vibes, she soon began going down a new route. By 2002, Spears was not afraid to come across as a bit of a bad girl — and this ultra-cool look (via Vice) was the perfect way to spice up her image. At the 2002 VMAs, Spears wore a striking all-black look consisting of leather and lace: an asymmetrical leather mini dress with a studded V-neck and a lace patch on one thigh paired with a leather Newsboy cap, rather Madonna-esque fingerless gloves, and knee-high lace-up boots.

This striking look is still remembered today. In fact, in 2016, Perrie Edwards from Little Mix apparently appreciated Spears' iconic look so much, she channeled the famous Y2K leather and lace getup when she donned a saucy leather Newsboy cap of her own (via Mirror).

During the 2002 Grammys, Britney Spears' good girl image was back in full swing. The singer appeared on the red carpet in a stunning bright red floor-length gown with a halo of tight curls in her hair. This was one time when Spears opted for some old school glamour instead of her usual Y2K look.

As the singer told Harper's Bazaar, it ended up being one of her favorite looks of all time. When asked by the magazine what her best look was, she described this look. "It wasn't short and saucy; it was a long red dress," she said. "That dress was fun." In 2021, the star posted a photo of herself in the dress on Instagram. "I got to hair and makeup in jeans and a sweatshirt and I left like this!!!!" Spears wrote. "It's taken me 19 years to realize that I was Julia Roberts in Pretty Woman.'"