The Best Oscar Dresses of All Time

The time is finally here! This Sunday, the 93rd Academy Awards will highlight some of the best films of the year. But movies aren’t the only things awarded this night. The best-dressed stars receive praise alongside their film accomplishments. The Oscars are notorious for being a formal event. So, people come Oscar Dress to the nines. From dramatic gowns to the traditional tuxedo, all of these styles grace the carpet. Many of the other award shows this year have been virtual. But the Oscars are mostly in-person, making for true grand entrances. These celebrities will definitely follow suit of their predecessors. So to celebrate the upcoming Academy Awards, let’s look back at some of the best fashions in Oscar history.

Natalie Portman (2020)

Natalie Portman's Oscars Tribute to Female Directors Is a Must-See - E!  Online
(Courtesy of E! Online)

Starting with one of the most recent styles Oscar Dress, Natalie Portman made headlines when she walked the red carpet. That year was filled with memorable directors, but not a single woman received a nomination. So, Portman had her Dior cape embroidered with Oscar-worthy women. She said in an interview, “I wanted to recognize the women who were not recognized for their incredible work this year, in my subtle way.”

Zendaya (2015)

Zendaya outraged by 'ignorant' dreadlocks remark
(Courtesy of USA Today)

Zendaya surprised everyone when she debuted her locs at the Oscars. But despite the controversy, her hairstyle complimented the softness of her dress. The off-the-shoulder moment made for a classic detail. So much so, children’s dolls were created in her honor.

Billy Porter (2019)

Billy Porter Slays Oscars 2019 Red Carpet With Velvet Tuxedo Dress |  HuffPost
(Courtesy of HuffPost)

Billy Porter is no stranger to bending gender norms. So Christian Siriano blended the classic tuxedo with a ballgown. The neckline to the waist was a fitted tux, with an oversized bowtie. But from the waist down was a full skirt. The dramatic outfit included black velvet throughout.

Cher (1974)

Cher Oscars Red Carpet Outfits - Cher's Best Oscar Moments
(Courtesy of Harper’s Bazaar)

The Academy Awards is the one event were sophisticated gowns are the norm. But Cher believed otherwise. The legend strutted in a floral two-piece. The colorful ensemble included a bandeau and bare midriff. Her hair was also adorned with flowers.

Lupita Nyong’o (2014)

Sunday Best: A standout among the stars — Lupita Nyong'o at the 2014  Academy Awards red carpet | The Seattle Times
(Courtesy of The Seattle Times)

Lupita made herself a fashion staple in her rise to stardom. But her 2014 custom Prada was one for the books. The Oscar winner wowed in a blue, pleated gown. Nyong’o usually turns heads in any shade. But the “Nairobi blue” was a memorable hue.

Jennifer Lawrence (2011)

Let's all take a look at Jennifer Lawrence's Oscars transformation
(Courtesy of Cosmopolitan)

Sometimes, less is more. Jennifer Lawrence stunned in a red, Calvin Klein gown. The simplicity of the gown made her the focal point. But the silhouette and cross-wrap made casual look red carpet-worthy.

Audrey Hepburn (1954)

Emma Stone's Unexpected Oscar Connection to Audrey Hepburn | Vanity Fair
(Courtesy of Vanity Fair)

As one of the most iconic actresses of all time, her dress had to match as well. Audrey Hepburn secured an Oscar win in an ivory, sleeveless gown. The number also included floral print, a thin belt, and a neckline that brushed the collarbone. The dress is so popular, it was up for sale at an auction with a hefty price tag.

Lady Gaga (2017)

Lady Gaga Is Wearing Both Pants And A Dress To The Oscars - MTV
(Courtesy of MTV)

It’s not too often that you get to see pantsuits at the Academy Awards. But Lady Gaga changed that when she walked on the carpet in a white outfit. The suit featured a sweetheart neckline. But where the drama begins is the back. The material gathered together, making for am elegant train.

Barbara Streisand (1969)

Oscar Rewind: Pop Star Plays a Performer and Wins? It's Happened Before -  The New York Times
(Courtesy of The New York Times)

Already established as a musician, Streisand wanted to take a fashion risk into her film career. She opted for a sheer pantsuit, complete with plastic sequins. To contrast, the wrists and collar was a stark white material. To top it off, Streisand also wore a bowtie with the criticized ensemble.

Chadwick Boseman (2018)

Chadwick Boseman's Jacket Is King of the 2018 Oscars Red Carpet - E! Online
(Courtesy of E! Online)

Chadwick Boseman was known for his red carpet outfits. This 2018 suit in particular crowned him as one of the best Oscar Dresses actors of the night. His ensemble included an embellished coat and front-zipped shoes. His red carpet look proved that actors can wear more than tuxedos.


Cover photo Vanity Fair

About author


Brianna Ormond is a senior at Rutgers University as a Journalism and Media Studies major, Political Science and Africana Studies double minor. She enjoys listening to music and binging Netflix in her spare time.
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