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The Academy Awards is perhaps the most glamorous televised event, with millions of people tuning in to see who’s nominated, who wins, and just as importantly, who’s wearing what. Alongside the MET Gala, the Academy Awards is an annual event where the red carpet doubles as a runway, showcasing some of the best and most iconic dresses donned by the world’s most recognisable film A-listers. We’ve listed down just a few of the very best Oscar dresses of all time from the 1950s to today.

Audrey Hepburn in Givenchy (1954)

We’re beginning this list of Oscar dresses with one of Hollywood’s most recognisable fashion icons and Hollywood royalty, Audrey Hepburn, in a dress considered to be one of the most classic looks of the 20th century. The actress accepted the Best Actress Oscar for her role in Roman Holiday wearing this white floral number by Givenchy. 

The actress and designer were great friends throughout their careers, with Hepburn sporting many of his gowns at special events as well as casual clothing off-screen. The waist-cinched dress with a boat neckline was the very first dress of the partnership and is an Audrey Hepburn classic that would go down in fashion history right next to her Breakfast at Tiffany’s little black dress.

Julia Roberts in Vintage Valentino (2001)

In 2001, Julia Roberts sported a black gown that would go down as one of the most memorable Oscars red carpet dresses. Julia Roberts wore the dress at the 73rd Academy Awards when she won the Best Actress trophy for her starring role in Erin Brockovich. 

The vintage Valentino gown featured a single white stripe running down the front of the dress, splitting into a Y-shape at the bust to form a pair of straps, while the back of the dress featured a black tulle train with several more white stripes running along it.

Jennifer Lawrence in Calvin Klein (2011)

Before winning the Best Actress award for her role in Silver Linings Playbook at the 2013 Academy Awards, the first appearance Jennifer Lawrence would make on the award show’s red carpet would be two years prior when she received her first nomination for Best Actress. 

While her winning dress was definitely an iconic look, we love how she made her debut in this simple yet sleek red dress from Calvin Klein which was eye-catching all on its own, not needing any other embellishments or accessories. We can tell that this is another piece that will be added to the list of best Oscars dresses to stand the test of time.

Grace Kelly in Edith Head (1955)

Nothing was as classically elegant and timeless as this dress by Edith Head worn by Grace Kelly at the 27th Academy Awards. The actress, who would retire from acting the following year to marry Prince Rainier III of Monaco, wore this breathtaking icy blue gown as she accepted the Best Actress Oscar for her performance in The Country Girl. 

The mint green silk Oscar dress featured a ruched skirt and elegant train, while an accessory of white gloves gave the outfit an air of old Hollywood glamour.

Winona Ryder in Armani (2000)

While not immediately recognisable as one of the best Oscar dresses of all time, we definitely think this dress belongs on the list for its sleek and timeless look, as well as the fact that Ryder had worn this dress multiple other times.

While the Academy Awards are the number one place to flaunt one-of-a-kind red carpet style, the actress would sport this column dress with a fitted bodice and curved neckline at other red carpet events before the 2000 Academy Awards. 

We love how much she loved the dress, and we also adore how she styled the piece with an accent shawl and simple black headband. This goes in our books as an absolutely iconic fashion moment from the 90s grunge style icon.

Nicole Kidman in Christian Dior Couture (1997)

Considered one of the most iconic Oscar dresses to have ever graced the red carpet, Nicole Kidman rocked up to the 69th Academy Awards alongside then-husband Tom Cruise wearing a bright Christian Dior dress. All eyes were on her and that Christian Dior gown that year, as it was completely different from anything else that was considered the norm for Oscar dresses at the time. 

The form-fitting, chartreuse number designed by Dior’s newest creative director, John Galliano, was incredibly striking, featuring Asian-inspired embellishments or chinoiserie. The dress put John Galliano on the fashion map as a daring creative new mind, and Kidman in the hall of most influential and best Oscars dresses ever.

Lupita Nyong’o in Prada (2014)

Lupita Nyong’o captured hearts in this Prada dress at the 2014 Academy Awards, where she won the Best Supporting Actress Oscar for her role in 12 Years a Slave. The powder blue silk gown may appear simple, but the low cut at the front and back, all-over pleating, subtle crystal details at the edges of the pleats, and dreamy flowing skirt completely make this piece classic yet memorable. 

We also love the simple accessories that embellish the dress, with a simple headband adorning the head of Lupita Nyong’o feeling like a tiara atop this princess ensemble. While we love Oscar dresses that take risks as much as everyone else, classic looks like this one easily stand the test of time and will be looked at for inspiration for years to come.

Michelle Williams in Vera Wang (2006)

At the 78th Academy Awards, Michelle Williams would appear on the red carpet wearing one of the most acclaimed Vera Wang Oscar dresses ever. 

Michelle Williams, who was nominated that evening for the Best Supporting Actress award, donned this saffron-yellow Vera Wang gown with dramatic ruffles, which was custom-made by Vera Wang and painstakingly cut to complement Williams’ body.

Angelina Jolie in Atelier Versace (2012)

For the 84th Academy Awards, Angelina Jolie wore this stunning custom Atelier Versace dress made with luxe velvet. The black strapless number featured asymmetrical cuts that added dimension to the otherwise understated piece, and the infamously high slit at the skirt added that level of sex appeal Jolie is known for. 

We love this understated Atelier Versace dress for its simple yet striking silhouette, and it has definitely made rounds on the internet as one of the most memorable, and arguably one of the best, Oscars dresses we’ve seen.

Halle Berry in Elie Saab (2002)

This Eli Saab dress that Halle Berry wore to the 74th Academy Awards was an absolute jaw-dropper, and set a trend for “second-skin” clothing after it was first seen on the red carpet. The dress featured a mesh top with flower embroidery and a wine red skirt, a daring yet simultaneously elegant never-before-seen look. 

Many consider this, and Nicole Kidman’s Dior dress, to be among the most influential and best Oscars dresses of the time, having started trends and changed Oscar dresses worn on the red carpet for years to come.

The dress itself wasn’t the only iconic thing that night; Halle Berry, in Elie Saab, would that night become the first black woman to win the Oscar for Best Actress.

Emma Stone in Givenchy Couture (2017)

At the 89th Academy Awards, Emma Stone would step out onto the red carpet wearing this beaded Givenchy gown, something already cemented as one of the best Oscar dresses we’ve ever seen, before winning her very own Academy Award for her lead role in La La Land. 

The gold, Swarovski-embellished gown features intricate detailing on the bodice, while the skirt fringe hem is reminiscent of 20s flapper fashion. 

Aside from what a radiant piece this gown is, we also love the fact that this was the second Givenchy Oscar dress to be worn by a Best Actress winner, the first being the equally iconic Audrey Hepburn dress. We hope to see more Givenchy Oscars dresses in best dresses lists to come.

Gwyneth Paltrow in Ralph Lauren (1999)

In 1999, Gwyneth Paltrow cemented her position in the Academy Awards red carpet history when she wore this taffeta dress by Ralph Lauren. 

The pink gown, which she wore to accept the Best Actress trophy for her role in Shakespeare in Love, was made of taffeta and featured a relatively simple design, with a V-shaped neckline and thin straps on the bodice and a full skirt, accessorised with a matching scarf and minimal diamond jewellery. After its debut, the Ralph Lauren ensemble would become widely copied and was credited for bringing pink back into fashion.

Paltrow would continue to turn heads on the red carpet in various Oscars dresses throughout the years. Another memorable piece she would be spotted in was an all-white Tom Ford dress with a matching cape in 2012, oozing red carpet glamour.

Jennifer Lopez in Elie Saab (2015)

Another absolutely stunning gown from just a few years ago, Jennifer Lopez writes this Elie Saab piece as an entry for a position among the all-time best Oscar dresses. 

The beaded Elie Saab gown is made with flowing nude tulle covered with beading beginning at the deep V-neckline and dripping down into the full ballgown skirt. We fell in love with how this all-over sparkling monochromatic look was chic and dazzling and is definitely one of the most stunning Oscar dresses we’ve seen on J-Lo.

Lady Gaga in Alexander McQueen (2019)

Lady Gaga arrived at the Academy Awards, where she received two nominations for her work in A Star is Born, wearing a dramatic black gown by Alexander McQueen, accessorised by the iconic Tiffany Diamond from Tiffany Co., being only the third person to wear it at a major award ceremony in its 142-year history. 

We love how she channelled Audrey Hepburn through her look, who had also worn the Tiffany Diamond for Breakfast at Tiffany’s publicity photos. 

The dress, while classic, is imbued with Lady Gaga’s signature statement fashion that she has been known for throughout her career, with a unique structured shape at the hips and partnered with leather gloves. We think this all-black ensemble is one of the best Oscar dresses we’ve ever seen.

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Lucy Coleman

Lucy Coleman is a freelance writer and fashion enthusiast hailing from Edinburgh. She discovered her knack for both style and writing while studying at university and decided to pursue her passions thereafter. When she’s not going through racks of clothing at different shops in her spare time, Lucy enjoys listening to music, writing stories at cafés, and catching up to her favourite shows on Netflix.

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