20 of the most daring looks of the 2000s

20 of the most daring looks of the 2000s

While stars turned heads with their bold fashion choices in the '90s, the new millennium introduced us to looks more daring than ever before.

Stars including Jennifer Lopez, Lil Kim, Katy Perry, and Christina Aguilera wore jaw-dropping outfits to red-carpet events, while trends including mega-low-rise jeans and deep-V necklines gained momentum.

Here are 20 of the most daring looks of the noughties, or early 2000s.

Pink's spiky hair and ultra-low-rise pants are just some of the reasons her 2000 VMAs look was one for the books.

Pink at the 2000 MTV VMAs.
Pink at the 2000 MTV VMAs.Ron Galella/Getty Images

At her first VMA appearance, Pink certainly made a name for herself. In 2015, MTV called this busy, eccentric look a "very loud statement."

In a hot-pink, spiky hairdo, the singer wore a shiny jacket lined with fur; a high-necked, gold, cropped tank top; gold chains draping over her very low-rise jeans; and large hoop earrings.

The 2000 VMAs proved to be a night full of daring looks — Christina Aguilera wore a revealing sequin outfit.

Christina Aguilera in 2000.
Christina Aguilera in 2000.Michael Ochs Archives/Getty Images

At the 2000 VMAs, Christina Aguilera wore a black, sparkly dress that exposed her torso. Her thong was also visible, adding another daring element to the look.

According to i-D, this look is exemplary of how the VMAs often features "the music industry's most outrageous (and most iconic) red carpet looks."

Sarah Jessica Parker tied tulle around her arm while wearing a feathered dress at the 2000 Emmy Awards.

Sarah Jessica Parker at the 2000 Emmy Awards.
Sarah Jessica Parker at the 2000 Emmy Awards.Steve Granitz/Getty Images

Sarah Jessica Parker's ultra-feathery pink dress at the 2000 Emmy Awards was designed by Oscar de la Renta.

In a 2014 essay for The Hollywood Reporter, Parker honored the late fashion designer and discussed the public's mixed reactions to her look.

"I remember the first time I was invited to Mr. de la Renta's office and asked if he might build a dress for me for the 2000 Emmys," she wrote. "It turned out to be a pink dress with a feathered skirt that people had a lot of opinions about — mostly because I tied a big piece of tulle on my arm."

Jennifer Lopez wore a Versace gown at the 2000 Grammys that was daring enough to inspire the creation of Google Image search.

Jennifer Lopez in 2000.
Jennifer Lopez in 2000.Scott Gries/Getty Images

"Daring" might be an understatement when it comes to J-Lo's 2000 Grammy's gown, which had a neckline that plunged down to her navel.

As Insider previously reported, the dress "sent the internet into meltdown," and the public's reaction was a catalyst for the image-search feature on Google.

Eric Schmidt, the former executive chairman of Google, explained in a 2019 essay published on Project Syndicate, "At the time, it was the most popular search query we had ever seen. But we had no surefire way of getting users exactly what they wanted: J.Lo wearing that dress."

As a result, Schmidt said, "Google Image Search was born."

In what might be the most iconic couples' red-carpet look of the 21st century, Britney Spears and Justin Timberlake rocked denim outfits at the 2001 American Music Awards.

Britney Spears and Justin Timberlake wearing all denim outfits.
Britney Spears and Justin Timberlake in 2001.Jeffrey Mayer/Getty Images

The couple, who started dating in 1999 and split in 2002, "made blue-jeans history with this version of the Canadian tuxedo," Insider's Tayler Adigun wrote. She named it one of "the most iconic celebrity couple looks of all time."

In 2014, Katy Perry and Riff Raff replicated the look, and Spears tweeted at Perry in appreciation of the tribute.

"Just when I thought the denim dress had retired....you bring it back!" she wrote.

At the 2001 Hip-Hop Music Awards, Lil Kim wore a bra top that left her chest exposed.

Lil Kim in 2001.
Lil Kim in 2001.KMazur/Getty Images

With nothing but stick-on, bedazzled stars covering her chest, her barely there two-piece set was just one of the rapper's many daring red-carpet looks.

Spears wore an all-lace, long-sleeved mini dress to the 2001 VMAs.

Brittany Spears in 2001.
Spears in 2001.KMazur/Getty Images

The lacy mini dress that exposed her undergarments wasn't Spears' most shocking appearance of the night. After the red carpet, she performed "Slave 4 U" while holding a live snake, in what is considered one of the pop-star's most iconic performances.

Aguilera rocked an ultra-mini skirt and a scarf-shirt at the 2002 VMAs.

Gwen Stefani in 2002.
Gwen Stefani in 2002.Jeff Kravitz/Getty Images

In addition to her tiny, low-rise denim skirt and the top E! News referred to as "racy," she wore a white hat and tall black boots.

At the 2002 Oscars, Halle Berry wore a partially sheer dress with flower details that covered her chest.

Halle Berry at the 2002 Oscars.
Halle Berry at the 2002 Oscars.Jeff Kravitz/Getty Images

The top of her red Elie Saab dress was made of sheer mesh, but embroidered flowers allowed her chest to stay covered.

In this gown, she accepted the Academy Award for best actress, becoming the first Black woman in history to receive the honor.

Avril Lavigne added daring details to a casual outfit at the 2002 VMAs.

Avril Lavigne in 2002.
Avril Lavigne in 2002.Jim Spellman/Getty Images

In 2002, Avril Lavigne showed up to the VMAs in a casual, yet unique, outfit. In lieu of a necklace, the pop artist hung a tie — featuring the Canadian flag — loosely around her neck. She wore baggy, low-rise, camouflage cargo pants that exposed the band of her underwear, and she completed the look with spiky wristbands.

Wearing a similar punk, camouflage look, Gwen Stefani rocked a unique, studded leather skirt to the 2002 VMAs.

Gwen Stefani in 2002.
Gwen Stefani in 2002.KMazur/Getty Images

The skirt Gwen Stefani wore with her otherwise simple outfit had tiers of studded leather hanging from a buckle between her legs.

In 2002, Paris Hilton paired an off-the-shoulder shirt that read "Savage Art" with a torn mini skirt.

Paris Hilton in 2002.
Paris Hilton in 2002.Christopher Polk/Getty Images

Under a fur coat, Hilton wore a white, two-piece set, with a top that read "Savage Art" over a leopard-print background. Her skirt appeared torn at its end.

She wore the unique look, which she completed with a fluffy white bag, to a Pussycat Dolls performance in Hollywood, according to W Magazine.

Aguilera struck again at the 2003 VMAs sporting an entirely different style.

Christina Aguilera in 2003.
Christina Aguilera in 2003.Stephen Lovekin/Getty Images

Although her pink, feathery mini dress offered more coverage than her VMAs look from the year prior, she still went for a bold red-carpet look.

Ashley Tisdale seemed to have worn just about everything in her closet to the premiere of "Ice Princess" in 2005.

Ashley Tisdale in 2005.
Ashley Tisdale in 2005.Jon Kopaloff/Getty Images

Disney Channel star Ashley Tisdale layered a gold sequin skirt over a pair of jeans, and a white graphic T-shirt over a blue tank top. She completed the look with gold flats, a chunky turquoise necklace, and a clutch that looked like piano keys.

In an 2019 essay for Garage, writer Emma Specter wrote, "As Tisdale's style demonstrates, sometimes wearing everything you've got, all at once, is the move. Frankly, our current muted, neutral-hued Instagram monoculture could use a little more of it."

Hilary Duff mixed patterns, colors, and textures at the 2003 Nickelodeon Kids' Choice Awards.

Hillary Duff in 2003.
Duff in 2003.Jeffrey Mayer/Getty Images

In a mesh, flowery top, a mini skirt with ruffles that appeared to be made of lacy handkerchiefs, and heeled boxer boots, the "Lizzie McGuire" star certainly showed the audience her playful side at the Kids' Choice Awards.

Katy Perry wore giant eyeballs on her chest at the 2008 MTV Europe Music Video Awards in England.

Katy Perry in 2008.
Katy Perry in 2008.Mark Cuthbert/Getty Images

Putting a twist on an otherwise simple red-carpet look, the "I Kissed a Girl" singer's dress featured a pair of green eyeballs in place of a traditional bodice.

Rihanna's corset was covered in spikes at the 2008 American Music Awards.

Rihanna in 2008.
Rihanna in 2008.Jon Kopaloff/Getty Images

Silver chains hung from Rihanna's black leather corset, which was full of spikes that matched the shape of the two awards she won that night: favorite pop/rock female artist and favorite soul/R&B female artist.

White diamonds protruded from the dress Lady Gaga wore to the 2008 Jingle Ball in New York City.

Lady Gaga in 2008.
Lady Gaga in 2008.Kevin Mazur/Getty Images

Lady Gaga, whose debut single, "Just Dance," was released earlier that year, paired her spiky dress with white gloves.

In 2009, she wore another three-dimensional look to a red-carpet appearance.

Lady Gaga in 2009.
Lady Gaga in 2009.Jason LaVeris/Getty Images

The then-up-and-coming artist took geometric patterns to a whole new level in this angular, all-black, 3-D look, which she wore to 102.7 KIIS-FM's Wango Tango in Irvine, California.

Rihanna wore a puffy-sleeved suit to the Met Gala in 2009.

Rihanna at the 2009 Met Gala.
Rihanna at the 2009 Met Gala.WWD/Getty Images

She paired the Dolce & Gabbana suit, which featured exaggerated shoulder pads, with plain black heels.

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