12 Best Dresses in Oscar History

Zendaya Oscars
Zendaya Oscars (Source: POPSUGAR)

12 Best Dresses in Oscar History!!

The Academy Award, commonly known as the Oscars, is undoubtedly the most prestigious award in the film industry.

However, it is not about the worth of the award statuette but the significance it presents!

Red Carpet at the Oscars (Source Business Insider)

And, it is an equally big deal on how celebrities attend this glorious event- what are they wearing, who is the designer, is it meeting the theme, and so on!

The Academy Award always has a dress code, and this is a big time for celebrities to show off their best dresses.

If you did not know this already, an A-list actress’ outfit cost ranges from tens of thousands of dollars to tens of millions of dollars. And, we can never forget Cate Blanchett’s 2014 Oscar outfit worth $18.1 million, making it the most expensive dress in Oscars yet!

Now that we know how big this dress thing is let us present you with the top 12 best dresses in Oscar history!

Quick Overview

Here are the top 12 best dressed Oscar winners of all time!!

S.no Worn By Designer Year
1. Grace Kelly Edith Head 1955
2. Sharon Stone Gap and Vera 1998
3. Gwyneth Paltrow Ralph Lauren 1999
4. Julia Roberts Valentino 2001
5. Halle Berry Elie Saab 2002
6. Michelle Williams Vera Wang 2006
7. Angelina Jolie Atelier Versace 2012
8. Jennifer Lawrence Dior Haute Couture 2013
9. Lupita Nyong’o Prada 2014
10. Lady Gaga Alexander McQueen 2019
11. Sandra Oh Elie Saab 2020
12. Zendaya Valentino Haute Couture 2021

Best Dresses In Oscar History

#1. Grace Kelly

Grace Kelly, originally Grace Patricia Kelly (1929-1982), was an American actress from Philadelphia.

The actress appeared in 11 movies and delivered very promising work in American film history. However, she abandoned her acting career in 1956 and tied the nuptial knot to Rainier III, Prince de Monaco.

Grace Kelly with her Oscar (Source: Pinterest)
Grace Kelly with her Oscar (Source: Pinterest)

To detail, the best work of Kelly is remembered to be in those classic Alfred Hitchcock movies.

Likewise, Grace received an Oscar for her impactful role in The Country Girl (1954). The actress went to receive the award wearing Edith Head ice-blue gown.

The beautiful gown boasted French satin worth $4,000, and she paired it with an evening coat matching her ensemble.

Moreover, she completed her look with a crimson lip and stunning updo, which made her look oh-so-elegant in that blue champagne gown!

#2. Sharon Stone

The American actress and former model Sharon Stone is popularly known for portraying the character of a femme fatale or a woman of mystery in movies.

Born in 1958, Sharon Stone took a sabbatical from work as she was hospitalized for a hemorrhage. Moreover, the actress faced professional challenges while she was on her route to recovery.

Sharon Stone in Oscars 1998 (Source: Insider)
Sharon Stone in Oscars 1998 (Source: Insider)

Now talking about the Oscars, Sharon wore a beautiful Vera Wang skirt which is considered as the coolest fashion move of the Academy award.

To add further, Stone pulled off this look by balancing it with a basic white shirt. The overall ensemble was from Gap and Vera. This proved that sometimes it takes minimal to rock the show!

#3. Gwyneth Paltrow

The American actress as well as the businesswoman Gwyneth Paltrow was born in 1972.

The talented actress is the recipient of several awards of high degrees, including Oscars, Golden Globe, Emmy, and Screen Actors Guild (SAG) Award.

Gwyneth Paltrow
Gwyneth Paltrow (Source: Marie Claire)

But here, we are talking about how Paltrow outdid herself during the Academy Award ceremony of 1999.

To illustrate, Gwyneth carried a pink Ralph Lauren gown in which she looked flawsome. Moreover, she wore a Harry Winston diamond choker that brought the ensemble a full circle.

That choker was purchased for Gwyneth by her late father, Bruce Paltrow. With this elegant look, she looked radiant while receiving the Best Actress Award for her work in Shakespeare in Love (1998).

#4. Julia Roberts

Julia Roberts is one of the most financially successful Hollywood actresses. To detail, Roberts had appeared in a lead role in various movies from different genres.

In 2001, the veteran actress wore a classic black gown designed by Valentino.

Julia Roberts Oscar Dress (Source: Refinery29)
Julia Roberts Oscar Dress (Source: Refinery29)

As a matter of fact, Valentino admitted being nervous when Julia carried this black outfit and stayed all night to find out if she wore it. Goodness, she did, and boy, she looked beautiful.

To add further, the black and white dress was floor-length and, Julia Roberts carried it so well while receiving the Oscar for her performance in Erin Brockovich (2000).

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#5. Halle Berry

The first runner-up of Miss USA beauty pageant, Halle Berry, is an American actress as well as a model.

In 2001, Berry clad herself in an Elie Saab outfit when she attended the Academy Award ceremony.

Halle Berry Oscar Dress (Source: CR Fashion Book)
Halle Berry Oscar Dress (Source: CR Fashion Book)

The actress looked gorgeous in that bare clothing with her fabulous pixie haircut.

Berry in that mesh embroidered gown won an Oscar in the category of Best Actress for the 2001’s film Monster’s Ball.

A little extra great detail: Halle Berry that year became the first black woman to win an Academy Award for the Best Actress.

#6. Michelle Williams

The talented American actress Michelle Williams is prominently known for her work in small-budget films, primarily focusing on tragic themes.

Williams has been honored with several accolades, including two Golden Globe for her role in Fosse/Verdon (2020) and My Week With Marilyn (2012).

Michelle Williams at Oscar 2006 (Source: Harper's Bazaar)
Michelle Williams at Oscar 2006 (Source: Harper’s Bazaar)

Likewise, she is the recipient of various nominations for best actress and best supporting actress.

In 2006, Williams wore a beautiful gown from Vera Wang to the Oscars. To illustrate, Michelle completed the classic saffron gown with a strong scarlet lip.

The exquisite canary yellow dress matched the red carpet and made this dress one of the best dresses worn at the ceremony.

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#7. Angelina Jolie

The woman needs no introduction, yet let’s keep it subtle. Angelina Jolie is one of the best actresses in Hollywood, known for her beauty and skilled acting.

Jolie has rocked several red carpet looks, however, here we are talking about her 2012’s outfit that created quite a buzz.

Best Dresses In Oscar History- Angelina Jolie in 2012's Oscar Ceremony (Source: People.com)
Angelina Jolie in 2012’s Oscar Ceremony (Source: People.com)

For the Academy Award look, Angelina opted Atelier Versace, the velvet gown with a thigh-high slit flaunting her right leg.

History remembers how sexy Angie looked when she stuck her leg out of that holy dress!

#8. Jennifer Lawrence

The Hunger Games actress Jennifer Lawrence is famously known as the queen of casual looks. As a matter of fact, no one else carries the laid-back attitude as she does.

Nonetheless, in 2013, the queen went for something different, highly glamorous.

Best Dresses In Oscar History- Jennifer Lawrence at the Oscar (Source: Marie Claire)
Jennifer Lawrence at the Oscar (Source: Marie Claire)

For the fact she won Best Actress that year for her role in Silver Linings Playbook, Lawrence clad herself in a pale blush Dior Haute Couture gown.

Moreover, she completed her look with a Chopard 74-carat diamond necklace. The very necklace had 150 diamond beads falling backward.

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#9. Lupita Nyong’o

The Kenyan-Mexican actress Lupita Nyong’o won the Academy Award for Best Supporting Actress in 12 Years a Slave (2013).

Best Dresses In Oscar History- Lupita Nyong'o
Lupita Nyong’o (Source: The Independent)

Nyong’o was born in Mexico City and was raised in Kenya. It was her debut in 12 Years a Slave, for which she wore a beautiful baby blue Prada gown.

Lupita looked beautiful in this colorful, airy gown and had her moment on the red carpet.

#10. Lady Gaga

How can anybody write or talk about red carpet looks and not mention the queen herself, the OG Lady Gaga?

No matter how many bizarre outfits she has carried over all these years, here, we are talking about the best dresses worn at the Oscars.

Best Dresses In Oscar History
Lady Gaga at Oscar 2019 (Source: People.com)

In 2019, Gaga looked gorgeous in the Alexander McQueen gown. The late Alexander McQueen also shared a brief friendship with Lady Gaga.

Gaga carried this strapless, structured black gown so elegantly and chose a 128-carat diamond necklace to complete the look.

Moreover, it was the same diamond piece originally worn by Audrey Hepburn.

#11. Sandra Oh

The Canadian actress Sandra Oh is known for her starring roles in TV shows like Killing Eve (2018-2022) and Grey’s Anatomy (2005-).

Best Dresses In Oscar History- Sandra Oh
Sandra Oh (Source: POPSUGAR)

In 2020, Sandra wore a dazzling sparky gown designed by Elie Saab, and it was immediately loved by everyone, thus holding a position in the list of best Oscar dresses of all time.

To illustrate, the gown boasted intricate poufy sleeves and a gorgeous metallic bow.

#12. Zendaya

One of the most loved and talented women of today’s date, Zendaya, is an American actress and a singer. Her real name is Zendaya Maree Stoermer Coleman.

In 2021, she presented herself in a Valentino Haute Couture. The actress looked stunning in this neon yellow dress, showing off her midriff.

Best Dresses In Oscar History- Zendaya at Oscar 2021 (Source: POPSUGAR)
Zendaya at Oscar 2021 (Source: POPSUGAR)

Moreover, she completed the look with a breath-taking piece from Bulgari High jewelry. The cut-out Bulgari necklace she wore looked illuminating with her custom gown, bringing her on the list of best dressers.

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