Jennifer Lopez at the Grammy Awards (2000)
This Versace gown was originally modelled by Amber Valletta, but the world went gaga when J-Lo wore it at the 2000 Grammys. When she presented on stage with The X-Files actor David Duchovny, he famously said: "This is the first time in five or six years I'm sure that nobody is looking at me."
Britney Spears and Justin Timberlake at the American Music Awards (2001)
If the general public needed any convincing that Britney and Justin were the It-couple to end all It-couples, this was it. The twosome attended the 2001 AMAs in matching denim outfits that are still spawning imitations.
Victoria Beckham at the Met Gala (2004)
Former Spice Girl (and future fashion designer) VB marked her Met Gala debut with this sheer Dolce & Gabbana dress, attending with Naomi Campbell as her partner.
Courtney Love at the Golden Globe Awards (2000)
Courtney Love caused a stir at practically every turn-of-the-century awards show she went to (let's not forget when she threw a shoe at Madonna at the 1995 MTV VMAs). At the 2000 Golden Globes, the singer turned plenty of heads with her risky Dior by John Galliano dress.
Paris Hilton at her 21st birthday party (2002)
Hilton's 21st dress was designed by Julien Macdonald, and is about as emblematic of the 2000s as it gets. Model Kendall Jenner even wore a dupe of the famous dress for her very own 21st birthday party in 2016.
Naomi Campbell at the Met Gala (2001)
The theme for the 2001 Met Gala was 'Jacqueline Kennedy: The White House Years'—but by the look of her outfit, Naomi Campbell might have missed the memo. She attended the event in a bold t-shirt and sheer skirt, alongside her close friend Stefano Gabbana, who wore ripped, badge-adorned jeans.
Björk at the Academy Awards (2001)
Björk turned the Academy Awards dress code on its head when she arrived at the 2003 awards in a comedic swan dress by designer Marjan Pejoski. If she wasn't a household name by then, the instantly-iconic dress helped her become one.
Lara Flynn Boyle at the Golden Globes (2003)
This ballerina-inspired mini skirt (featuring ribbon-adorned heels) was likely a Carrie Bradshaw tribute gone awry, and saw Twin Peaks actress Lara Flynn Boyle make pretty much every worst-dressed list of 2003.
Halle Berry at the Academy Awards (2001)
Berry won her first Oscar for Monster's Ball at the 2001 Academy Awards—and her risqué sheer gown was a career-making moment for couturier Elie Saab.
Hilary Swank at the Academy Awards (2005)
When Swank won the Oscar for Million Dollar Baby in 2005, her Guy Laroche dress became one of the most iconic in Oscars history. Leaving her front completely covered, the rear of the dress left her back completely exposed, in a plunging back that stopped just above her derrière.
Amber Valletta at the Met Gala (2004)
The theme of the 2004 Met Gala was 'Dangerous Liaisons' (like the famous film), so there was unsurprisingly an expectation to go above and beyond. However, supermodel Amber Valletta's take on aristocrat style—with a very fitting Dior by John Galliano skirt—is one of the most memorable in the history of the Met.
Gwyneth Paltrow at the Academy Awards (2002)
Paltrow's Alexander McQueen gown couldn't have been more different from the pink satin Ralph Lauren dazzler she wore to accept her Oscar for Shakespeare In Love in 1999. In 2013, Paltrow said: "I still love the dress itself, but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to—a little bit of punk at the Oscars."
Nicole Kidman at the Met Gala (2003)
Nicole Kidman's Gucci by Tom Ford gown was undeniably a classic, but the sheer panel across her chest nearly exposed all—and proved the perfect revenge dress after her tumultuous divorce from Tom Cruise.
Britney Spears and Christina Aguilera at the MTV VMAs (2003)
Spears and Aguilera's turns as sexy brides at the VMAs (coupled with both of them kissing Madonna on stage) led to a barrage of complaints to MTV, saying the performance infringed on family-friendliness.
Faith Hill at the Academy Awards (2002)
The early-2000s Oscars ceremonies might have been a treasure trove of zany looks, but none came quite close to Faith Hill's over-the-top Versace dress, which featured almost every colour of the rainbow.
Sarah Jessica Parker and Alexander McQueen at the Met Gala (2006)
Okay, so we know 2006 isn't the early '00s, but it would be criminal not to mention Sarah Jessica Parker's overwhelming tartan moment at that year's Met Gala, which she attended with the late, great Alexander McQueen.
Lil' Kim at the MTV VMAs (1999)
Likewise, Lil' Kim's look at the September 1999 VMAs fell a few months short of the 2000s, but set a new standard for risqué awards show dressing in the coming decade.