The Most Iconic Best Actress Oscar Winner Dresses Of The 2000s, Ranked

Hollywood's biggest night also happens to be one of fashion's. The evening in question is, of course, the Academy Awards. Cinephiles and fashion obsessives alike are glued to their phones and TVs — the latter are eyeing the red carpet to clock who's wearing what, why, and how well. The Oscars are a major style night, especially for the Best Actress nominees who could be about to make history. And, oh yes, there will be photos. The 2000s, in particular, produced a host of amazing films and some iconic red-carpet looks. After all, we were ushering in a new millennium, and thus, a new era of fashion.  

The worst-dressed celebs at the 2026 Oscars tended to miss the mark due to a lack of polish or because they just didn't seem to meet the moment. As a whole, the Oscar winners of the 2000s showed up much better. But if we're considering dresses that people are still buzzing about two decades later, some were more successful than others. We ranked the best looks by their iconic appeal.

When Kate Winslet won the Best Actress Oscar for her role in "The Reader" in 2009, she accepted her award in a gray Yves Saint Laurent gown that left much to be desired. The silvery shade is classic and we love the beaded skirt, but for the 81st annual Academy Awards, something punchier would have been more befitting a movie star and nominee. This is the dress a PR girl working the red carpet wears so she doesn't steal focus. Not our favorite, but Winslet is always an icon.

At the 79th Academy Awards in 2007, Dame Helen Mirren aptly took home the Best Actress Oscar for portraying Queen Elizabeth II in "The Queen." We couldn't think of anyone better suited for the role, but the fabrics used in the Christian Lacroix gown didn't quite work together. The royal inspiration was clear, and the beaded top is ornate is totally gorgeous, but it loses some of its luster up against the print of the skirt, which would have been more at home in a daytime look than in evening wear.

It's rare that Charlize Theron doesn't bring it with her red carpet looks, and the 76th Academy Awards in 2004 were no exception. The South African actor looked stunning in Gucci when she accepted the Best Actress Oscar for her role in "Monster," a crowd favorite. Theron opted for a beige-colored gown covered in stones that was perfectly pretty but lacked that oomph. But a special shout-out to the Old Hollywood finger waves and the bleached brows. So good. 

When she won the best actor Oscar for "Walk the Line," Reese Witherspoon donned vintage Dior to the 78th annual ceremony in 2006. The classic A-line and the gorgeous, ornate detailing was a great choice for a Southern belle and America's sweetheart. Witherspoon's Oscar gown was lower on our list only because it felt a little dated — there's a way to make vintage feel fresh again — but more than that, it was too mature for a then-30-year-old actor. Maybe more modern styling could've helped the whole look read younger.

There are plenty of casual ways to style your favorite little black dress, but at the 75th annual Academy Awards in 2003, Nicole Kidman showed us how to elevate it for a formal event without losing that dark glamour. When she won the Best Actress Oscar for playing Virginia Woolf in "The Hours," Kidman wore a sheer, light-as-air Jean Paul Gaultier dress. The intricate straps and the ethereal draping offered tons of interest — your eye can't help but dance around. 

For the 72nd Academy Awards in 2000, the first of the Y2K era, Hilary Swank made us swoon in a Randolph Duke ballgown that perfectly encapsulated that lovely little sliver of time when the fashion of the late '90s was morphing into that of the early 2000s. Note the straight strapless neckline, the draped full skirt, the gothic green fabric, and the statement necklace — relics of both periods. On that night, Swank took home the Best Actress Oscar for her groundbreaking role in "Boys Don't Cry." 

In 2001, when Julia Roberts nabbed the Best Actress Oscar for the titular role in the biopic "Erin Brockovich," she reached for vintage Valentino. She told People in 2017, "I guess the one that gets the most commentary is probably my look for the Oscars for 'Erin Brockovich.'" And for good reason. Her gown for 73rd annual Academy Awards featured delicate white stripes overlaid onto velvety black and subtle, expertly-placed bits of sheer fabric — it all came together for a look that oozed elegance and Hollywood glamour, and one that's etched in our fashion memories.

For the 77th annual Academy Awards in 2005, Hilary Swank took home her second Best Actress Oscar; this time for "Million Dollar Baby." For the ceremony and to the Vanity Fair after-party, Swank donned a deceptively simple Guy Laroche backless gown to rival all backless gowns. Some might think it was too plain, but it breached the top 3 because it's a masterclass in quiet elegance and understated glamour. The color is beautiful, and the fit is sublime —and without a back panel! That right there is deserving off all the gold statues.

French actor Marion Cotillard brought the playful energy of the Grammys to the 80th annual Academy Awards in 2008 , and it totally worked. The Oscars, steeped in history and tradition, doesn't tend to be the event where the most fashion risks are taken, but Cotillard's sea-worthy gown, courtesy of Jean Paul Gaultier, expertly blended whimsy and elegance. Cotillard took the stage to accept the Best Actress Oscar for her lead role in "La Vie En Rose" covered in glitter-trimmed scales and serving full-on majestic mermaidcore.

At the 74th annual Academy Awards in 2002, Halle Berry made history in more than one way. She won the Best Actress Oscar for her portrayal of Leticia Musgrove in "Monster's Ball," the first Black woman to win an Oscar in a leading role. Berry accepted the award in an iconic Elie Saab gown. With its mesh top, pretty petal embroidery, draped ball skirt, and regal Bordeaux color, it's securely situated on most people's lists of the best Oscars dresses of all time. And it was definitely a catalyst for the stunning style transformation of Halle Berry.

To settle on placement on the list, we, of course, looked at the beauty and design of the dresses. From there, we considered uniqueness, appropriateness for the event, and how much risk was taken by the actors. Also, we took into account our collective memory and the cultural impact of the gown and of the moment.