20 of the most daring looks of the 2000s

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.

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'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."

"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."

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.

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.

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.

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.

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.

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.

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

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.

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.

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."

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.

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. 

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.

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

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.

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