These Were the Best Red Carpet Looks From the Early 2000s, Hands Down

If you did a deep dive back into the many celebrity red carpet moments of the early 2000s, you'll be reminded that it was a wild time on that magical crimson carpet. Given the Y2K revival in fashion, these archival images are more relevant than ever. Looking through these images, it almost feels like some of them could've been taken in 2022. Hot pink, low-rise waistlines, and micro-mini hemlines abound, but there are also timeless gowns that would be on the best-dressed lists for this year's Oscars ceremony.

I dug through hundreds of red carpet images from 2000 to 2010, and while it wasn't easy to narrow it down to just 15 winners, I did my very best. Below, see what Anne Hathaway, Cameron Diaz, Jennifer Lopez, and more were wearing approximately 20 years ago, and shop early 2000s-inspired pieces that meet the moment.


Britney Spears, 2002 American Music Awards
(Image credit: Kevin Mazur/WireImage)

This hot-pink dress and matching pink heels reminds me of the Barbiecore moment we're living in. It was one of the pop princess's chicest red carpet appearances, in my humble opinion.


Jennifer Lopez, 2003 Gigli Premiere
(Image credit: Frank Trapper/Corbis via Getty Images)

Jennifer Lopez's plunging brown dress was sophisticated without being stuffy. I'd love to see her wear this exact look again.

On Jennifer Lopez: Roberto Cavalli dress


Cameron Diaz, 2003 Golden Globe Awards
(Image credit: Kevin Winter/Getty Images)

This fun, flirty Chanel look is a departure from the gowns you usually see on the red carpet, and that's why I love it.

On Cameron Diaz: Chanel Haute Couture dress


Penelope Cruz, 2000 Oscars
(Image credit: Kevin Mazur/WireImage)

Penelope Cruz's azure gown, which she paired with simple jewelry and hair and makeup was perfection.

On Penelope Cruz: Ralph Lauren dress


Rihanna, 2009 Met Gala
(Image credit: Chance Yeh/Patrick McMullan via Getty Images)

Rihanna's glammed-up tuxedo and leather gloves were ingenious at the time, and a departure from the sea of gowns that were commonplace at the Met Gala.

On Rihanna: Dolce & Gabbana suit


Blake Lively, 2009 Emmy Awards
(Image credit: Dan MacMedan/WireImage)

This was Blake Lively's best red carpet look to date, hands down.

On Blake Lively: Versace dress


Keira Knightley, 2003 Pirates of the Caribbean World Premiere
(Image credit: Lester Cohen Archive/WireImage)

I had to include this because I'm sure everyone's jaws dropped when she stepped on the Pirates of the Caribbean premiere red carpet wearing this. It was fun and unexpected, just like the film's star herself.


Anne Hathaway, 2009 Oscars
(Image credit: Steve Granitz/WireImage)

This shimmery column gown solidified Anne Hathaway as a red carpet star, which she continues to be to this day.

On Anne Hathaway: Armani Privé dress


Kate Bosworth, 2008 21 Premiere
(Image credit: Jeff Kravitz/FilmMagic)

Kate Bosworth has really racked up the great red carpet looks over the years, but this silver Chanel look really captured her fashion girl essence.

On Kate Bosworth: Chanel Haute Couture dress


Halle Berry, 2002 Oscars
(Image credit: Steve Granitz/WireImage)

The jaw-dropping sheer gown, which Halle Berry won her Oscar in, is one of the most memorable Oscar dresses of all time.

On Halle Berry: Elie Saab dress


Sarah Jessica Parker, 2000 Emmy Awards
(Image credit: SGranitz/WireImage)

This whimsical, perfectly tailored dress suited SJP to a T. Carrie Bradshaw fans everywhere rejoiced.

On Sarah Jessica Parker: Oscar de la Renta dress


Lucy Liu, 2000 Oscars
(Image credit: Wally Skalij/Los Angeles Times via Getty Images)

This stunning dress was pure Versace and pure Lucy Liu. And it holds up—it's tough to guess what year it's from—that's how timeless it is.

On Lucy Liu: Versace dress


Taylor Swift, 2008 Met Gala
(Image credit: Dimitrios Kambouris/WireImage)

Taylor Swift looked like a gilded goddess at the 2008 Met Gala. The fact that it was her first Met Gala appearance makes it even more impressive.

On Taylor Swift: Badgley Mischka dress


Michelle Williams, 2006 Oscars
(Image credit: Chris Polk/FilmMagic)

Michelle Williams took home an Oscar wearing this memorable saffron-colored dress. It's not a color you often see on the red carpet, and that's one of the things that makes it so special.

On Michelle Williams: Vera Wang dress


Salma Hayek, 2005 AmFAR Event
(Image credit: J. Vespa/WireImage)

If you're thinking that you wish you owned this perfect hot pink dress today, you're definitely not alone.

Shop Early 2000s-Inspired Pieces

Next up, the best celebrity Cannes outfits from the '90s.

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.