The Biggest '00s Fashion Icons

The Y2K era is often maligned for its fashion choices, but the recent resurgence of '00s fashion trends speaks to the decade's underrated splendor. After all, this was the era of The Devil Wears Prada and Legally Blonde, of Sex and the City and The Hills. Love or hate the tube dresses and capris, the chunky belts and dresses over jeans, you can't deny the cultural impact of the period.

But that impact isn't really about the aforementioned chunky belts and capris—it's about the women who wore them (and, in turn, convinced us they were a good idea). The influence of these '00s fashion icons may haunt your old photo albums, but they deserve recognition all the same.

Paris and Kim

Any list of '00s style influences would be incomplete without Paris Hilton and Kim Kardashian—divisive though they may be, their debut on the red carpet scene meant that beauty and fashion would be profoundly impacted. Even beyond the decade, we love to discuss these two.

Amanda Bynes

Amanda Bynes was the unsung style hero of the '00s, both in the cult classic What a Girl Wants and the fan favorite She's the Man. Go back and review those films, and you'll see some of the best '00s trends done very well—and her red carpet style was great, too.

Jenna Dewan

The star of Step Up and then-wife of Channing Tatum, Jenna Dewan was an extremely reliable presence on the red carpet—trendy but cute, usually in extremely high heels and some really amazing hair. (Those particular qualities would extend well beyond the '00s, but this was the decade we first took notice.)

'The Hills' Stars

Ah yes. If someone asks you to recall celebrities that defined this decade, odds are good that a star from The Hills would be high on the list. These coordinating strappy dresses are very of the time, but your group of female friends dressed exactly the same way.

Katie Holmes

The breakout star of Dawson's Creek captured hearts and minds with her sweet, feminine style—both on the show and off. Katie Holmes' short bob and blunt bangs, which she debuted after the show ended, meant that she would remain a fashion and beauty influence for all of us.

Sarah Michelle Gellar

Buffy the Vampire Slayer would extend into the early '00s, and we all took note of what Sarah Michelle Gellar's character was wearing every week. Off-screen, Gellar's style was softer but equally fun; minus a few of the frills, I wouldn't mind wearing this now.

Avril Lavigne

The girl-punk aesthetic would never be the same, thanks to Avril Lavigne's pink-highlighted hair and chunky accessories. While not everyone was a fan of her aesthetic at the time, a dose of hindsight reveals how fun, edgy, and creative her style was.

Hilary Duff

For the average middle schooler, there was no more relatable teen than Lizzie McGuire. Hilary Duff, who made the character iconic, also had a youthful enthusiasm in her red carpet style that we loved. Did it always work? No, but she is working the heck out of that Coach bucket hat.

Nicole Richie

While she originally became known as Paris Hilton's BFF, Nicole Richie would revamp her persona in the late 2000s with the launch of lifestyle brand House of Harlow. That business venture would also coincide with a new, chic style that was very minimal-'00s in a way I appreciated.

The Stars of 'High School Musical'

Few people expected the High School Musical movies or its stars to be quite so much of a cultural sensation. The range of styles for high school inspo, from Gabriella to Taylor to Sharpay (with Troy as our collective boyfriend, naturally) was pretty incredible.

Jennifer Lopez

Jennifer Lopez has an impressively long trajectory in her fashion evolution—she's both innovator, as with her 2000 Grammys Versace dress that broke the internet, and chameleon. Here she channels some bad '00s trends with enthusiasm, including tracksuit and pageboy hat, with about as much success as anyone can.

Christina Milian

In the grand tradition of "everything old is new again," there's no greater signifier that the '00s is being re-appreciated as a decade than the fact that Christina Milian has starred in a bunch of Netflix rom-coms. She was our '00s style queen, and I applaud having her back on my TV!

Jessica Simpson

It is unfortunate that Jessica Simpson's brand has often been reduced to "ditsy," because she's always been both smart and stylish. In fact, her Jessica Simpson Collection of clothes and accessories is the most successful celebrity licensing brand ever—and she rebought it in 2022 to rebuild it.

Christina Aguilera

Christina Aguilera really went there in her '00s aesthetic (think: chaps pants, pageboy hats, skunk hair highlights, barely-there tops), but I actually don't think she gets enough credit for being boundary-pushing. When she did it well—like the above—it was flawless.

Gwen Stefani

The late '90s, early '00s style of Gwen Stefani—characterized by short tops, baggy pants, tons of color and sparkles, plus some wild platinum hair and a deep red lip—will go down as one of the most influential styles for young people that ever existed.

Anne Hathaway

If you're unfamiliar, this is a still of Anne Hathaway from The Devil Wears Prada, which was a formative '00 movie for girls and women who loved style. Hathaway's character's style transformation was something we all longed for, and Hathaway's own evolving style in real life was equally cool.

Destiny's Child

Destiny's Child made dressing to match your BFFs (or, in this case, bandmates) deeply, unequivocally cool. They weren't the first "girl group" to do so, but their coordinating outfits were so on the nose in an amazing way that they redefined the concept entirely.

Beyoncé

It was always rumored that Beyoncé would go solo, but when she came into her own in the '00s, she gave us an elevated style that let us know, for certain, that she was a force to be reckoned with. And so a red carpet style icon (who wore the heck out of her signature gold color) was born.

Victoria Beckham

The Spice Girls broke up in 2001 (sheds millennial tears) and the former Posh Spice was crafting a new identity in the '00s: wife to a soccer superstar, solo singer, and fashionable presence in her own right. She would launch her own line in 2008 and would continue skyrocketing from there.

The 'Mean Girls' Girls

Some of the fashion from this movie—see also, "On Wednesdays, we wear pink!"—has been part of the reason it's had such a long cultural lifespan. The outfits that The Plastics (Lindsay Lohan, Amanda Seyfried, Lacey Chabert, and Rachel McAdams) wore will remain iconic.

Britney Spears

Britney Spears had an incredibly on-stage style, starting with schoolgirl-chic and just getting better from there. But I also liked her red carpet and casual style—she makes a jumpsuit look like a perfect shopping outfit, which is honestly hard to do.

Jennifer Aniston

Jennifer Aniston's been a red carpet presence for decades at this point. She often opts for chic and simple, going streamlined and straightforward in a way that's coherent to her personal style. And she really honed and perfected that formula in the '00s, as with this perfect red column dress.

The 'Charlie's Angels' Stars

Putting aside the debate about whether the rebooted Charlie's Angels movies were good (hot take: I liked them!), superstars Drew Barrymore, Cameron Diaz, and Lucy Liu had exceptional style in both movies. I'll ignore the fact that those heels would be tough to run in, because they're super-cute.

Janet Jackson

Janet Jackson remains under-appreciated for the impact she had on both music and style in the '00s (and beyond). Her red carpet style was impressively chic and sophisticated, but her on-stage style was graphic, edgy, fashion-forward, and highly emulatable even today.

Jennifer Garner

With the one-two punch of Alias and Daredevil, Jennifer Garner made very tight leather outfits look exceptional. I like to think of her aesthetic as "action star meets runway model," and I stand by that. She was a huge part of the reason we loved, and love, fitted jackets.

Julia Roberts

Julia Roberts is a fashion icon in her own right, excluding any movies she was a part of. But it was her Oscar-winning turn as Erin Brockovich, which gave us a lot of miniskirts, high heels, and sheer tops (and still looked amazing as heck), that brought in some joy and frivolity.

Aaliyah

The late singer and actor was just becoming a cultural and style icon when she died tragically in 2001. Her presence on the red carpet showed off just how much energy and discernment she put into her persona, with a unique edginess that she executed perfectly.

Reese Witherspoon

If you don't know, this is Reese Witherspoons as Elle Woods from Legally Blonde, which came out in 2001 and basically defined preppy-cute style for the next 10 years. (So much pink!!) It also helped define serotonin dressing and dressing to fit your personality—both impressive legacies.

Mary-Kate and Ashley Olsen

While The Row is now famous as a luxury brand, when Mary-Kate and Ashley Olsen founded it in 2006, it was seen as somewhat counterintuitive and surprising. They saw the gap in the market (luxury basics of exceptional quality) way before the rest of us.

Sarah Jessica Parker

There may be no other character—in this decade or otherwise—that left more of an imprint on fashion than Carrie in Sex and the City. It helped that the character was played by the equally iconic Sarah Jessica Parker, who wore the heck out of impressively challenging outfits, like this one, with ease.

Angelina Jolie

Playing Lara Croft in two movies just made sense for Angelina Jolie, who (at the time) was seen as Hollywood's resident bad*ss. She wore leather pants effortlessly, had a bunch of cool tattoos, and became an expert at knife-throwing on set. She really was just cooler than anyone else.

Kate Moss

The ubiquity of "festival style" might feel like a relatively new occurrence, but that's hardly the case. Back before anyone else was wearing wellies and short shorts, Kate Moss was casually attending the Glastonbury Festival as our collective fashion pioneer.