Oscars Dresses From The Early Aughts We'll Never Forget

The Met Gala is now considered the biggest night on the fashion calendar, but as far as awards shows go, the Oscars is where the magic happens. Events like the Grammys and the MTV Video Music Awards offer more wiggle room to experiment and have fun, but the Academy Awards ceremony is a beacon of formality and sophistication. Though there's no longer an official white tie dress code, attendees still mostly opt for elegant eveningwear — it's one of the last few events in Hollywood where you can turn up the drama in a ballgown and get away judgment-free. Naturally, the prestige attached to the Oscars has paved the way for some remarkable looks over the years. 

Thinking about the early noughties period in particular, Oscars fashion leveled up the glamour. Stars reached for archival gowns, sweeping trains, as well as those that pushed fashion boundaries in subtle ways. This was an era for polished updos (which made for some of the most iconic Y2K hairstyles), statement details, and classic silhouettes to reign supreme. The list of the best looks from this time would be endless, and we've already chronicled the worst-dressed celebs in Oscars history. So we're narrowing it down to those looks that we truly can't get out of our heads 20 years later, for better or for worse. 

Screen gods like Hilary Swank made red carpet moves that gave us whiplash in the best way, while other looks were so unforgettable because we're still trying to unpack them more than two decades later (sorry, Björk). This nostalgic era in Tinseltown history — free of Ozempic, social media, and outfits made to go viral in seconds — may be a mere memory, but thanks to the following looks, we'll have it forever. 

In 2001, Julia Roberts strayed from Oscars tradition when she wore a black-and-white Valentino column gown. It wasn't the fact that she won the award for Best Actress for her work in "Erin Brockovich" that had people talking, but that her iconic dress wasn't custom made for her, as was the etiquette at the time. It was first worn by model Helena Christensen in Valentino's AW92 couture presentation before Christy Turlington wore it in the October 1992 issue of Harper's Bazaar. Valentino Garavani himself later told The Telegraph that seeing Roberts win her Oscar in his dress made him feel "so very, very happy."

As "Bridget Jones" fans, we have always itched to see Renée Zellweger in a flawless white dress, signifying that our beloved hopeless romantic finally got her happy ending. Zellweger answered our prayers in bridal white at the 2004 Oscars, where she won an award for her work in "Cold Mountain." The distinct Carolina Herrera taffeta gown featured a simple strapless frontage with elaborate detail on the back, flowing into a Watteau train that gave it even more of a romantic feel. The "Judy" actor finished off the stunning look with a Cartier diamond choker.

In a complete 180 from the sweet pink Ralph Lauren ballgown Gwyneth Paltrow wore to the 1999 Oscars, she appeared at the 2002 event looking much moodier. The Alexander McQueen dress featured a nearly-naked sheer bodice with lace-up detail, paired with a heavy black maxi. Her smokey eye makeup and lace-style necklace gave this ensemble a gothic feel, but it was the see-through top that made this look unforgettable. Just over 20 years later, Apple Martin revived the frock for a full circle moment, making her one of the celebrity kids who inherited their parents' famous style.

Sheer dresses weren't super prevalent in the noughties, but the 2002 Oscars seemed to be the place to push buttons with this style. To accept the Best Actress award for "Monster's Ball," Halle Berry graced the stage in maroon-toned Elie Saab. The striking gown featured a transparent bodice and a heavy skirt with a dramatic train, but floral embroidery saved this look from feeling totally naked. In November 2024, Berry wowed fans when she brought the dress out of retirement to honor Elie Saab in Saudi Arabia. "There are some moments in life that just happen and they change our lives forever!" Berry wrote on Instagram. 

Not all dresses are unforgettable because they're stunning. More than 20 years later, the world isn't over Björk's Marjan Pejoski swan number from 2001. Featuring a body stocking studded with crystals, the bulk of the dress was made up by a white tulle swan wrapping its neck around the Icelandic singer's own neck. If the look itself weren't bizarre enough, Björk left a trail of eggs behind on the red carpet. "I thought it'd be very appropriate to wear a swan," she said (via BBC). "I guess they don't do those things anymore, right?" The dress was widely spoofed, but it has never been forgotten.

Kim Kardashian famously wore Marilyn Monroe's legendary sparkly dress to the Met Gala in 2022, but Charlize Theron was ahead of the game back at the 2004 Academy Awards. While she didn't wear Monroe's exact frock like Kardashian did, she did wear a Gucci piece that evoked the original gown's sheer sexiness, and styled her hair in glamorous '50s waves. While the front of the crystal-encrusted dress featured a simple plunging neckline and thigh slit, the strappy back brought a modern edge. It's no wonder she topped People's best-dressed list at the time.

Lucy Liu often flies under the fashion radar, but she's had some phenomenal red carpet moments, and her Versace look at the 2000 Oscars is the cream of the crop. The stunning one-shoulder dress was one of optical illusions, featuring sheer panels that came off looking metallic. While one X (formerly Twitter) user called it "my favorite Oscars look of all time," another summed it up adequately: "This is the best a human has ever looked." The gown wasn't shocking, but it was so exquisite that it's now seared in our minds forever.

The turn of the millennium was a huge time for Cameron Diaz, who was still riding the wave of her '90s romcoms while also embracing the "Charlie's Angels" media storm. She played the role of superstar fittingly at the 2000 Oscars, where she wore a black lacy gown from Versace. Given the fact that her underwear was on display at the prestigious award show, this inappropriate dress had everyone staring at Cameron Diaz. But fashion's in the eye of the beholder, and some critics thought the frock's simplicity made it a hit. Either way, we're not forgetting it anytime soon.

For the most part, Hilary Swank stays safe with understated looks on the red carpet. But she had us all doing a double take in 2005, when she appeared at the Academy Awards in a navy Guy Laroche design. From the front, it seemed like any other modest gown with a high neck; it was only when she turned to reveal a totally backless silhouette that we were stupefied. Originally, the "Million Dollar Baby" star had planned to wear Calvin Klein, so this high-fashion moment almost never happened. Perish the thought!

Beyoncé made her Oscars debut in 2005, when she attended to perform three songs that were nominated for the Best Original Song award: "Vois Sur Ton Chemin," "Learn to be Lonely," and "Believe," the last of which was performed with Josh Groban. She made a splash as only Bey can for her debut, draped in diamonds and a dramatic black velvet gown from Atelier Versace. Glamour was the aim of the game, and even with the many boundary-pushing looks that Beyoncé has worn since, this classic ensemble still stands out for its iconic energy.