Here They Are: The Best Oscars Looks Of All Time

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Eliza Huber
·8 min read
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Update: The Oscars were held in person on Sunday, April 26 — and the red carpet was full of top-tier fashion moments. See which looks from the occasion made our best-of-all-time list ahead.

This story was originally updated on April 23, 2021.

The finish line is in sight! A-listers have glammed up for the Golden Globes, mellowed out for the SAGs, and pulled out almost all the stops for the Grammys (albeit mostly from the comfort of their homes). But the mother of all award shows will always be the Oscars, and it's but a few short days away.

The sartorial brainstorming has begun for who’s going to be wearing what on Sunday night: Will Cynthia Erivo arrive in Valentino Haute Couture? Will we get another Vanessa Kirby in Gucci moment for the record books? Is it Oscar de la Renta for Mank's Amanda Seyfried? All we can do is wait and see.

In an effort to help pass the time between now and Sunday night, we're taking a trip down memory lane and reminiscing on the best red carpets of Oscars past. See which celebrities made the cut by clicking through the throwback looks ahead.

<h2>Audrey Hepburn, 1954<br></h2><br>It never took much to make the late Audrey Hepburn look glamorous, but in this Givenchy gown, Hepburn, glowing from winning an Oscar for <em>Roman Holiday</em>, is nothing short of perfection.<br><br><em>Audrey Hepburn in Givenchy.</em><span class="copyright">Photo: NBCU Photo Bank/Getty Images. </span>

Audrey Hepburn, 1954


It never took much to make the late Audrey Hepburn look glamorous, but in this Givenchy gown, Hepburn, glowing from winning an Oscar for Roman Holiday, is nothing short of perfection.

Audrey Hepburn in Givenchy.Photo: NBCU Photo Bank/Getty Images.
<h2>Grace Kelly, 1955<br></h2><br>Designed by arguably the most famous costumier in history, Edith Head, Grace Kelly's Oscars look was, like most Grace Kelly looks, an absolute winner.<br><br><em>Grace Kelly in Edith Head. </em><span class="copyright">Photo: Silver Screen Collection/Hulton Archive/Getty Images. </span>

Grace Kelly, 1955


Designed by arguably the most famous costumier in history, Edith Head, Grace Kelly's Oscars look was, like most Grace Kelly looks, an absolute winner.

Grace Kelly in Edith Head. Photo: Silver Screen Collection/Hulton Archive/Getty Images.
<strong><h2>Madonna, 1991</h2></strong><br>Dripping in Old Hollywood glamour, there's nothing we'd rather see Madonna wearing to the 63rd Annual Academy Awards than this Bob Mackie ensemble.<br><br><em>Madonna in Bob Mackie.</em><span class="copyright">Photo: Ron Galella/WireImage/Getty Images. </span>

Madonna, 1991


Dripping in Old Hollywood glamour, there's nothing we'd rather see Madonna wearing to the 63rd Annual Academy Awards than this Bob Mackie ensemble.

Madonna in Bob Mackie.Photo: Ron Galella/WireImage/Getty Images.
<h2>Winona Ryder, 1994<br></h2><br>Who doesn't love a Gatsby-esque gown at the Oscars? <span class="copyright">Photo: Ron Galella Collection/Getty Images.</span>

Winona Ryder, 1994


Who doesn't love a Gatsby-esque gown at the Oscars? Photo: Ron Galella Collection/Getty Images.
<strong><h2>Elizabeth Hurley, 1995</h2></strong><br>Head-to-toe white? Sweetheart neckline? Floor-length sequins? Check! Check! Check!<br><br><em>Elizabeth Hurley in Versace.</em><span class="copyright">Photo: Jim Smeal/WireImage/Getty Images. </span>

Elizabeth Hurley, 1995


Head-to-toe white? Sweetheart neckline? Floor-length sequins? Check! Check! Check!

Elizabeth Hurley in Versace.Photo: Jim Smeal/WireImage/Getty Images.
<strong><h2>Winona Ryder, 1996</h2></strong><br>While we're used to seeing '90s-era Winona Ryder donning all-black ensembles, it was an unexpected surprise to see her donning this champagne-colored vintage gown.<br><br><em>Winona Ryder in a vintage champagne gown. </em><span class="copyright">Photo: Jim Smeal/WireImage/Getty Images. </span>

Winona Ryder, 1996


While we're used to seeing '90s-era Winona Ryder donning all-black ensembles, it was an unexpected surprise to see her donning this champagne-colored vintage gown.

Winona Ryder in a vintage champagne gown. Photo: Jim Smeal/WireImage/Getty Images.
<strong><h2>Courtney Love, 1997</h2></strong><br>The queen of grunge got all dolled up by Versace for the 1997 Academy Awards — and we support it 100%.<br><br><em>Courtney Love in Versace. </em><span class="copyright">Photo: Jim Smeal/WireImage/Getty Images. </span>

Courtney Love, 1997


The queen of grunge got all dolled up by Versace for the 1997 Academy Awards — and we support it 100%.

Courtney Love in Versace. Photo: Jim Smeal/WireImage/Getty Images.
<h2>Sharon Stone, 1998<br></h2><br>We would normally advise against wearing Gap at the Oscars — but when it's combined with Vera Wang and draped on Sharon Stone, it's hard <em>not</em> to be convinced that the casual brand right where it belongs.<br><br><em>Sharon Stone in Gap and Vera Wang.</em><span class="copyright">Photo: Mychal Watts/WireImage/Getty Images. </span>

Sharon Stone, 1998


We would normally advise against wearing Gap at the Oscars — but when it's combined with Vera Wang and draped on Sharon Stone, it's hard not to be convinced that the casual brand right where it belongs.

Sharon Stone in Gap and Vera Wang.Photo: Mychal Watts/WireImage/Getty Images.
<strong><h2>Celine Dion, 1999</h2></strong><br><br>A suit on the red carpet is hardly a nuanced idea in 2021. But, in 1999, and worn backward of all things, well, let's just say our fashion minds were blown upon seeing Celine Dion in this John Galliano set.<br><br><em>Celine Dion in John Galliano.</em><span class="copyright">Photo: SGranitz/WireImage/Getty Images. </span>

Celine Dion, 1999



A suit on the red carpet is hardly a nuanced idea in 2021. But, in 1999, and worn backward of all things, well, let's just say our fashion minds were blown upon seeing Celine Dion in this John Galliano set.

Celine Dion in John Galliano.Photo: SGranitz/WireImage/Getty Images.
<strong><h2>Gwyneth Paltrow, 1999</h2></strong><br><em>Pretty In Pink</em> might have starred Molly Ringwald, but Gwyneth Paltrow (that year's Best Actress winner for <em>Shakespeare in Love) </em> looked the part in this bubblegum pink number by Ralph Lauren.<br><br><em>Gwyneth Paltrow in Ralph Lauren. </em><span class="copyright">Photo: Frank Trapper/Corbis/Getty Images. </span>

Gwyneth Paltrow, 1999


Pretty In Pink might have starred Molly Ringwald, but Gwyneth Paltrow (that year's Best Actress winner for Shakespeare in Love) looked the part in this bubblegum pink number by Ralph Lauren.

Gwyneth Paltrow in Ralph Lauren. Photo: Frank Trapper/Corbis/Getty Images.
<h2>Queen Latifah, 2000<br></h2><br>Blue is <em>definitely</em> Queen Latifah's color.<br><br><em>Queen Latifah in a blue dress. </em><span class="copyright">Photo: Steve Granitz/WireImage/Getty Images. </span>

Queen Latifah, 2000


Blue is definitely Queen Latifah's color.

Queen Latifah in a blue dress. Photo: Steve Granitz/WireImage/Getty Images.
<h2>Renée Zellweger, 2001</h2><br>A long way from donning PJs all day and micro-minis at work in her role as Bridget Jones, Renée Zellweger classed up for the red carpet in a vintage yellow frock by Jean Dresses.<br><br><em>Renée Zellweger in a vintage dress by Jean Dresses.</em><span class="copyright">Photo: Chris Weeks/Getty Images. </span>

Renée Zellweger, 2001


A long way from donning PJs all day and micro-minis at work in her role as Bridget Jones, Renée Zellweger classed up for the red carpet in a vintage yellow frock by Jean Dresses.

Renée Zellweger in a vintage dress by Jean Dresses.Photo: Chris Weeks/Getty Images.
<h2>Halle Berry, 2002</h2><br>To become the first Black woman to win Best Actress, Halle Berry eliminated her competition — both on the red carpet and the stage — in this Elie Saab gown.<br><br><em>Halle Berry in Elie Saab.</em><span class="copyright">Photo: Kevin Mazur/WireImage/Getty Images. </span>

Halle Berry, 2002


To become the first Black woman to win Best Actress, Halle Berry eliminated her competition — both on the red carpet and the stage — in this Elie Saab gown.

Halle Berry in Elie Saab.Photo: Kevin Mazur/WireImage/Getty Images.
<h2>Charlize Theron, 2004</h2><br>Is Charlize Theron ever not glowing?<br><br><em>Charlize Theron in Dior.</em><span class="copyright">Photo: Jeff Kravitz/FilmMagic/Getty Images.</span>

Charlize Theron, 2004


Is Charlize Theron ever not glowing?

Charlize Theron in Dior.Photo: Jeff Kravitz/FilmMagic/Getty Images.
<strong><h2>Beyoncé Knowles, 2005</h2></strong><br>There to perform not one, not two, but three songs, Beyoncé went with a black velvet number that was made for her. <em>Thanks, Atelier Versace! </em><br><br><em>Beyonce Knowles in Atelier Versace. </em><span class="copyright">Photo: ROBYN BECK/AFP/Getty Images. </span>

Beyoncé Knowles, 2005


There to perform not one, not two, but three songs, Beyoncé went with a black velvet number that was made for her. Thanks, Atelier Versace!

Beyonce Knowles in Atelier Versace. Photo: ROBYN BECK/AFP/Getty Images.
<strong><h2>Michelle William, 2006</h2></strong><br>Accompanying her then-boyfriend, the late Heath Ledger, Michelle Williams was a shining ray of light in this yellow number by Vera Wang.<br><br><em>Michelle Williams in Vera Wang.</em><span class="copyright">Photo: Frazer Harrison/Getty Images. </span>

Michelle William, 2006


Accompanying her then-boyfriend, the late Heath Ledger, Michelle Williams was a shining ray of light in this yellow number by Vera Wang.

Michelle Williams in Vera Wang.Photo: Frazer Harrison/Getty Images.
<strong><h2>Nicole Kidman, 2007</h2></strong><br>Nicole Kidman in Balenciaga would hardly be our first choice in 2021, but after seeing the Oscar-winning Australian actress in this red hot gown, we promise to never doubt the combination again.<br><br><em>Nicole Kidman in Balenciaga.</em><span class="copyright">Photo: Frazer Harrison/Getty Images. </span>

Nicole Kidman, 2007


Nicole Kidman in Balenciaga would hardly be our first choice in 2021, but after seeing the Oscar-winning Australian actress in this red hot gown, we promise to never doubt the combination again.

Nicole Kidman in Balenciaga.Photo: Frazer Harrison/Getty Images.
<strong><h2>Anne Hathaway, 2009</h2></strong><br>Is it just us, or does Anne Hathaway look like an actual Oscar in this fitted Armani Privé dress?<br><br><em>Anne Hathaway in Armani Privé.</em><span class="copyright">Photo: John Shearer/WireImage/Getty Images. </span>

Anne Hathaway, 2009


Is it just us, or does Anne Hathaway look like an actual Oscar in this fitted Armani Privé dress?

Anne Hathaway in Armani Privé.Photo: John Shearer/WireImage/Getty Images.
<h2>Cate Blanchett, 2011<br></h2><br>In this lavender Haute Couture gown by Givenchy, Cate Blanchett wasn't just an award-winning actress — she's a damn fashion <em>icon.</em><br><br><em>Cate Blanchett in Givenchy Haute Couture.</em>

Cate Blanchett, 2011


In this lavender Haute Couture gown by Givenchy, Cate Blanchett wasn't just an award-winning actress — she's a damn fashion icon.

Cate Blanchett in Givenchy Haute Couture.
<h2>Michelle Williams, 2012 </h2><br>Wearing red on the red carpet isn't for the faint of heart. Nonetheless, Michelle Williams, nominated for her role as Marilyn Monroe in <em>My Week With Marilyn</em>, made it look like the easiest task in the world, thanks to one hell of a pixie cut and <a href="https://www.instyle.com/news/oscars-2012-michelle-williams-dress-took-300-hours-make" rel="nofollow noopener" target="_blank" data-ylk="slk:300 hours of work" class="link rapid-noclick-resp">300 hours of work</a> in the Louis Vuitton Paris atelier.<br><br><em>Michelle Williams in Louis Vuitton.</em><span class="copyright">Photo: Bob Riha, Jr./Getty Images. </span>

Michelle Williams, 2012


Wearing red on the red carpet isn't for the faint of heart. Nonetheless, Michelle Williams, nominated for her role as Marilyn Monroe in My Week With Marilyn, made it look like the easiest task in the world, thanks to one hell of a pixie cut and 300 hours of work in the Louis Vuitton Paris atelier.

Michelle Williams in Louis Vuitton.Photo: Bob Riha, Jr./Getty Images.
<h2>Angelina Jolie, 2012</h2><br>No one does a high slit quite like Mrs. Smith herself, Angelina Jolie, who generated one of the greatest Oscar memes ever with this pose.<br><br><em>Angelina Jolie in Atelier Versace. </em><span class="copyright">Photo: Donato Sardella/WireImage/Getty Images. </span>

Angelina Jolie, 2012


No one does a high slit quite like Mrs. Smith herself, Angelina Jolie, who generated one of the greatest Oscar memes ever with this pose.

Angelina Jolie in Atelier Versace. Photo: Donato Sardella/WireImage/Getty Images.
<h2>Jennifer Lawrence, 2013</h2><br>En route to accept her Oscar for <em>Silver Linings Playbook</em>, Jennifer Lawrence had all eyes on her in this pastel-colored Dior gown. It was pretty chill, even for her.<br><br><em>Jennifer Lawrence in Dior.</em><span class="copyright"> Photo: Gregg DeGuire/WireImage/Getty Images. </span>

Jennifer Lawrence, 2013


En route to accept her Oscar for Silver Linings Playbook, Jennifer Lawrence had all eyes on her in this pastel-colored Dior gown. It was pretty chill, even for her.

Jennifer Lawrence in Dior. Photo: Gregg DeGuire/WireImage/Getty Images.
<h2>Lupita Nyong'o, 2014 </h2><br>Lupita Nyong'o — who won Best Supporting Actress for her role in<em> 12 Years a Slave</em> — lit up the sky in this baby blue Prada gown.<br><br><em>Lupita Nyong'o in Prada.</em><span class="copyright">Photo: Axelle/Bauer-Griffin/FilmMagic/Getty Images.</span>

Lupita Nyong'o, 2014


Lupita Nyong'o — who won Best Supporting Actress for her role in 12 Years a Slave — lit up the sky in this baby blue Prada gown.

Lupita Nyong'o in Prada.Photo: Axelle/Bauer-Griffin/FilmMagic/Getty Images.
<h2>Zendaya, 2015 </h2><br>For an Oscars newbie, Zendaya looked anything but out of place in this Vivienne Westwood stunner of a gown.<br><br><em>Zendaya in Vivienne Westwood.</em><span class="copyright">Photo: Dan MacMedan/WireImage/Getty Images. </span>

Zendaya, 2015


For an Oscars newbie, Zendaya looked anything but out of place in this Vivienne Westwood stunner of a gown.

Zendaya in Vivienne Westwood.Photo: Dan MacMedan/WireImage/Getty Images.
<h2>Sienna Miller, 2015</h2><br>For his red carpet debut designing for Oscar de la Renta, Peter Copping made quite the impression with this bow-embellished, square neck gown on Sienna Miller.<br><br><em>Sienna Miller in Oscar de la Renta.</em><span class="copyright">Photo: Gregg DeGuire/WireImage/Getty Images. </span>

Sienna Miller, 2015


For his red carpet debut designing for Oscar de la Renta, Peter Copping made quite the impression with this bow-embellished, square neck gown on Sienna Miller.

Sienna Miller in Oscar de la Renta.Photo: Gregg DeGuire/WireImage/Getty Images.
<h2>Olivia Wilde, 2016 </h2><br>Olivia Wilde going backless in Valentino Haute Couture? We'll take it.<br><br><em>Olivia Wilde in Valentino Haute Couture.</em><span class="copyright">Photo: Steve Granitz/WireImage/Getty Images. </span>

Olivia Wilde, 2016


Olivia Wilde going backless in Valentino Haute Couture? We'll take it.

Olivia Wilde in Valentino Haute Couture.Photo: Steve Granitz/WireImage/Getty Images.
<h2>Taraji P. Henson, 2017 </h2><br>Taraji P. Henson blew us back to the 1950s in this Alberta Ferretti Old Hollywood-esque velvet gown. And that necklace? Whew, we're getting excited just thinking about it.<br><br><em>Taraji P. Henson in Alberta Ferretti. </em><span class="copyright">Photo: Frazer Harrison/Getty Images. </span>

Taraji P. Henson, 2017


Taraji P. Henson blew us back to the 1950s in this Alberta Ferretti Old Hollywood-esque velvet gown. And that necklace? Whew, we're getting excited just thinking about it.

Taraji P. Henson in Alberta Ferretti. Photo: Frazer Harrison/Getty Images.
<h2>Naomie Harris, 2017</h2><br>Of the four <em>Moonlight</em> stars dressed by Raf Simons for Calvin Klein, this white sequin frock on Naomie Harris took home the prize (for best-dressed) in our book.<br><br><em>Naomie Harris in Raf Simons for Calvin Klein.</em><span class="copyright">Photo: George Pimentel/FilmMagic/Getty Images.</span>

Naomie Harris, 2017


Of the four Moonlight stars dressed by Raf Simons for Calvin Klein, this white sequin frock on Naomie Harris took home the prize (for best-dressed) in our book.

Naomie Harris in Raf Simons for Calvin Klein.Photo: George Pimentel/FilmMagic/Getty Images.
<h2>Saoirse Ronan, 2018</h2><br>A long way from dress shopping at a Sacramento thrift shop! This bubblegum pink frock on <em>Lady Bird</em> lead actress Saoirse Ronan is one for the record books.<br><br><em>Saoirse Ronan in Calvin Klein By Appointment.</em><span class="copyright">Photo: Jeff Kravitz/FilmMagic/Getty Images. </span>

Saoirse Ronan, 2018


A long way from dress shopping at a Sacramento thrift shop! This bubblegum pink frock on Lady Bird lead actress Saoirse Ronan is one for the record books.

Saoirse Ronan in Calvin Klein By Appointment.Photo: Jeff Kravitz/FilmMagic/Getty Images.
<h2>Margot Robbie, 2018</h2><br>Margot Robbie was a breath of fresh air in this showstopping white gown courtesy of Chanel.<br><br><em>Margot Robbie in Chanel.</em><span class="copyright">Photo: Neilson Barnard/Getty Images.</span>

Margot Robbie, 2018


Margot Robbie was a breath of fresh air in this showstopping white gown courtesy of Chanel.

Margot Robbie in Chanel.Photo: Neilson Barnard/Getty Images.
<h2>Gemma Chan, 2019</h2><br>Hot pink came out running at the 91st Annual Academy Awards. But if you ask us, Gemma Chan won the marathon in this neon, tiered Versace dress.<br><br><em>Gemma Chan in Versace. </em><span class="copyright">Photo by Frazer Harrison/Getty Images.</span>

Gemma Chan, 2019


Hot pink came out running at the 91st Annual Academy Awards. But if you ask us, Gemma Chan won the marathon in this neon, tiered Versace dress.

Gemma Chan in Versace. Photo by Frazer Harrison/Getty Images.
<h2>Cynthia Erivo, 2020</h2><br>From the extra-high slit to the asymmetric neckline, this custom Versace gown includes everything that's good in the world. <br><br><em>Cynthia Erivo in custom Versace.</em><span class="copyright">Photo: Rick Rowell/Getty Images.</span>

Cynthia Erivo, 2020


From the extra-high slit to the asymmetric neckline, this custom Versace gown includes everything that's good in the world.

Cynthia Erivo in custom Versace.Photo: Rick Rowell/Getty Images.
<h2>Scarlett Johansson, 2020</h2><br>It's the peek-a-boo corset for us.<br> <br><em>Scarlett Johansson in Oscar de la Renta.</em><span class="copyright"> Photo: Amy Sussman/Getty Images.</span>

Scarlett Johansson, 2020


It's the peek-a-boo corset for us.

Scarlett Johansson in Oscar de la Renta. Photo: Amy Sussman/Getty Images.
<h2>Beanie Feldstein, 2020</h2><br>We'll never grow tired of Beanie Feldstein wearing Miu Miu on the red carpet. <br><br><em>Beanie Feldstein in custom Miu Miu. </em><span class="copyright"> Photo: Amy Sussman/Getty Images.</span>

Beanie Feldstein, 2020


We'll never grow tired of Beanie Feldstein wearing Miu Miu on the red carpet.

Beanie Feldstein in custom Miu Miu. Photo: Amy Sussman/Getty Images.
<h2>Regina King, 2021</h2>According to styling duo Wayman Bannerman and Micah McDonald, Regina King's winged, custom Louis Vuitton gown includes 6,000 crystals. (Casual.)<br><br><em>Regina King in custom Louis Vuitton.</em><span class="copyright">Photo: Chris Pizzello-Pool/Getty Images.</span>

Regina King, 2021

According to styling duo Wayman Bannerman and Micah McDonald, Regina King's winged, custom Louis Vuitton gown includes 6,000 crystals. (Casual.)

Regina King in custom Louis Vuitton.Photo: Chris Pizzello-Pool/Getty Images.
<h2>Zendaya, 2021</h2><br>Between the midriff cut-out, the 183 carats of Bvlgari diamonds, and the homage to Cher, Zendaya's 2021 Oscars look will go down in history. Did we mention that it glows in the dark? Yeah, it's that good. <br><br><em>Zendaya in custom Valentino. </em><span class="copyright">Photo: Chris Pizzello-Pool/Getty Images.</span>

Zendaya, 2021


Between the midriff cut-out, the 183 carats of Bvlgari diamonds, and the homage to Cher, Zendaya's 2021 Oscars look will go down in history. Did we mention that it glows in the dark? Yeah, it's that good.

Zendaya in custom Valentino. Photo: Chris Pizzello-Pool/Getty Images.

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