Oscars: The Best and Boldest Dresses of All Time

The gold standard for red carpet fashion has always been and will always be the Academy Awards. The red carpet is forever filled with gorgeous gowns, over-the-top ensembles and tons of bling.

[ami-related id="679" url="https://www.usmagazine.com/stylish/pictures/best-oscar-shoes-on-the-red-carpet-2015162/" title="Best Oscars Shoes on the Red Carpet" target="_blank" showsubt="false" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2020/02/Oscars-2020-Arrivals-Salma-Hayek-Slide.jpg"]

To reminisce on fabulous fashion moments, Stylish has decided to take a look back at some of the top styles that celebrities have worn in years past. And let Us just say, there have been some major style standouts! It shouldn’t come as too much of a surprise though, as the Academy Awards are historically the night to stun in Hollywood.

At the 2022 soirée, Zendaya wowed in a Valentino two-piece and Bulgari jewels that landed her on our best dresses list. One year prior, Regina King and Carey Mulligan landed on our best dressed list, dazzling Us with their best ensembles.

King wowed in a light blue custom Louis Vuitton gown, which featured embroidered sequins and crystals, a plunging neckline and 3-D sleeves. Mulligan, for her part, stepped out in a shimmery gold Valentino frock, featuring a cutout on her bodice, strapless neckline, and oversized skirt.

[ami-related id="2292469" url="https://www.usmagazine.com/stylish/pictures/oscars-2022-best-beauty-hair-makeup/" title="See the Best Beauty Looks at the Oscars" target="_blank" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2022/03/Feature-Jessica-Chastain-Best-Beauty-Gallery-Oscars-2022.jpg?quality=40&strip=all" imgid="2293108" format="gallery" flag="" channel="33"]

If we rewind to 1953, the style icon Audrey Hepburn made an iconic fashion statement, attending the Academy Awards in the same ivory lace gown she wore in her final scene of Roman Holiday, courtesy of her favorite designer Hubert de Givenchy.

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When Elizabeth Taylor was at the height of her fame in 1961, she accepted her Oscar for Butterfield 8 wearing a white and yellow Christian Dior gown with floral detailing. Shirley MacLaine hosted the 1975 event in a strapless floor-length standing alongside Sammy Davis Jr., Frank Sinatra, and Bob Hope.

And who could possibly forget Sharon Stone’s surprising look from 1996? Instead of attending in the typical ball gown or formal dress, the Casino actress showed up in a Gap turtleneck and Armani velvet coat.

[ami-related id="2460949" url="https://www.usmagazine.com/entertainment/pictures/oscars-2023-everything-to-know-about-the-academy-awards/" title="Everything to Know About the 2023 Academy Awards: Who’s Hosting, Who’s Nominated and More" target="_blank" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2023/03/Oscars-2023-001.jpg?quality=86&strip=all" imgid="3249037" format="gallery" flag="" channel="9"]

Regardless of the decade or trends at the time, Oscars fashion is always filled with jawdroppting ensembles, risqué choices and over-the-top looks. 

From Vivien Leigh‘s poppy gown in 1940 and Farrah Fawcett’s slinky gold Stephen Burrows’ gown in 1978 to Gwyneth Paltrow’s pink taffeta Ralph Lauren frock in 1999 and Halle Berry’s sheer Elie Saab design in 2002, the Academy Awards always deliver the best fashion.

So to take a trip through the past 94 years of Oscars fashion, keep scrolling, because we’re breaking down the best looks of all time.

The gold standard for red carpet fashion has always been and will always be the Academy Awards. The red carpet is forever filled with gorgeous gowns, over-the-top ensembles and tons of bling.

[ami-related id="679" url="https://www.usmagazine.com/stylish/pictures/best-oscar-shoes-on-the-red-carpet-2015162/" title="Best Oscars Shoes on the Red Carpet" target="_blank" showsubt="false" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2020/02/Oscars-2020-Arrivals-Salma-Hayek-Slide.jpg"]

To reminisce on fabulous fashion moments, Stylish has decided to take a look back at some of the top styles that celebrities have worn in years past. And let Us just say, there have been some major style standouts! It shouldn’t come as too much of a surprise though, as the Academy Awards are historically the night to stun in Hollywood.

At the 2022 soirée, Zendaya wowed in a Valentino two-piece and Bulgari jewels that landed her on our best dresses list. One year prior, Regina King and Carey Mulligan landed on our best dressed list, dazzling Us with their best ensembles.

King wowed in a light blue custom Louis Vuitton gown, which featured embroidered sequins and crystals, a plunging neckline and 3-D sleeves. Mulligan, for her part, stepped out in a shimmery gold Valentino frock, featuring a cutout on her bodice, strapless neckline, and oversized skirt.

[ami-related id="2292469" url="https://www.usmagazine.com/stylish/pictures/oscars-2022-best-beauty-hair-makeup/" title="See the Best Beauty Looks at the Oscars" target="_blank" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2022/03/Feature-Jessica-Chastain-Best-Beauty-Gallery-Oscars-2022.jpg?quality=40&strip=all" imgid="2293108" format="gallery" flag="" channel="33"]

If we rewind to 1953, the style icon Audrey Hepburn made an iconic fashion statement, attending the Academy Awards in the same ivory lace gown she wore in her final scene of Roman Holiday, courtesy of her favorite designer Hubert de Givenchy.

[sendtonews type="float" key="QtW7LYl660-2828768-14453"]

When Elizabeth Taylor was at the height of her fame in 1961, she accepted her Oscar for Butterfield 8 wearing a white and yellow Christian Dior gown with floral detailing. Shirley MacLaine hosted the 1975 event in a strapless floor-length standing alongside Sammy Davis Jr., Frank Sinatra, and Bob Hope.

And who could possibly forget Sharon Stone’s surprising look from 1996? Instead of attending in the typical ball gown or formal dress, the Casino actress showed up in a Gap turtleneck and Armani velvet coat.

[ami-related id="2460949" url="https://www.usmagazine.com/entertainment/pictures/oscars-2023-everything-to-know-about-the-academy-awards/" title="Everything to Know About the 2023 Academy Awards: Who’s Hosting, Who’s Nominated and More" target="_blank" thumb="false" imgsrc="https://www.usmagazine.com/wp-content/uploads/2023/03/Oscars-2023-001.jpg?quality=86&strip=all" imgid="3249037" format="gallery" flag="" channel="9"]

Regardless of the decade or trends at the time, Oscars fashion is always filled with jawdroppting ensembles, risqué choices and over-the-top looks. 

From Vivien Leigh‘s poppy gown in 1940 and Farrah Fawcett’s slinky gold Stephen Burrows’ gown in 1978 to Gwyneth Paltrow’s pink taffeta Ralph Lauren frock in 1999 and Halle Berry’s sheer Elie Saab design in 2002, the Academy Awards always deliver the best fashion.

So to take a trip through the past 94 years of Oscars fashion, keep scrolling, because we’re breaking down the best looks of all time.

For the 1940 Oscars, Leigh ditched the corsets and hoop skirts her Gone With the Wind character Scarlett O'Hara wore in the iconic film and instead wore this spaghetti strap dress by Irene Gibbons, featuring a lively poppy print and cut-outs at the waist.

The legendary actress asked designer Hubert de Givenchy to alter the ivory lace gown from her final scene of Roman Holiday so she could wear it to the 1953 Oscars, where she nabbed a Best Actress trophy for the film.

To accept her Oscar for Butterfield 8 in 1961, the screen siren wore a sleeveless Christian Dior gown with a yellow bodice and white ball-gown skirt with a floral pattern.

Yellow was the color of luck for Liza when she took home a Best Actress trophy for Cabaret wearing Halston's dress and jacket in 1972. Minnelli accessorized her evening ensemble with a choker necklace and yellow pumps.

With then-boyfriend Jack Nicholson as her date, Huston earned raves for her 1975 Oscar ensemble: A beige Halston gown with iridescent fish scale-like sequins. "Even though I worked as a Halston model, I had gotten this dress at Neiman Marcus," the actress has said of her gown. "The awards were on Friday, and [I bought it] on Wednesday."

The legendary actress glittered in a strapless floor-length gown when hosting the 1975 ceremony with Sammy Davis, Jr., Frank Sinatra, and Bob Hope.

The late Charlie's Angels icon dazzled on the red carpet in 1978 wearing Stephen Burrows' slinky gold chain-mail dress.

Thurman's lilac Prada gown helped put the fashion house on the map in 1995 when the actress wore it to celebrate her Best Supporting Actress nomination for Pulp Fiction.

The golden girl wanted "something that sparkled" for the 2003 awards and that's exactly what Donatella Versace gave her with this shimmering hand-sewn lace show-stopper.

Instead of wearing a typical over-the-top designer dress, the Casino actress turned up in a Gap turtleneck, Armani velvet coat and Valentino skirt in 1996.

The shocking chartreuse Dior creation (designed by John Galliano) Kidman wore in 1997 changed the red carpet fashion game for good.

Ralph Lauren designed this pink taffeta gown for Paltrow's 1999 appearance at the Oscars, where she took home a Best Actress trophy for her work in Shakespeare in Love.

The Zorro actress became an international superstar after wearing this strapless scarlet Versace in 1999.

Way before everyone in Hollywood decided backless dresses were a "thing," Theron wore this orange Vera Wang in 2000.

As if winning the Best Actress award (for Erin Brockovich) wasn't enough, the star became a fashion world legend with this vintage Valentino back in 2001.

For the 2001 ceremony, the Bridget Jones's Diary star looked radiant in a pale yellow vintage Jean Desses gown with a sweetheart neckline and delicate draping from the bodice.

In case the world didn't already know that she had a killer body, the actress showed it off in a sheer Elie Saab design when she won the Best Actress award for Monster's Ball in 2002.

Tons of stars have worn red gowns to the Oscars, but few have looked as incredible as Winslet did in her Ben de Lisi column in 2002.

No cleavage, no thigh-high slit and no skin-tight silhouette. Yet, Lopez managed to look sexier than ever in her mint green sari-style Valentinto in 2003. It didn't hurt that she accessorized with Ben Affleck.

Between her vibrant red hair and forest green Tom Ford for Yves Saint Laurent Rive Gauche gown, Moore was red carpet gold in 2003.  

Unlike other stars who get washed out by nude dresses or overpowered by feather embroidery, Lane looked more radiant and confident than ever in her 2003 Oscar de la Renta gown.

On anyone else the white silk-satin Marc Bouwer halter gown Jolie wore in 2004 would've looked like a fancy nightgown. On her it was pure Hollywood glamour.

The Best Supporting Actress winner for The Aviator accepted her 2005 Oscar in a custom lemon-colored one-shouldered Valentino gown.

In her backless midnight-blue Guy Laroche gown, the 2005 Best Actress winner (for Million Dollar Baby) proved that you don't need sequins to standout on the red carpet.

The actress, who attended the 2006 show with then-boyfriend Heath Ledger, made a bold sartorial choice when she paired bright red lips with a saffron-colored Vera Wang.

The British actress somehow managed to make this glamorous dark eggplant taffeta custom-made Vera Wang dress look young and fresh in 2006.

If you have a body as hot as Alba's, you're pretty much required to wear a sexy gold Versace look like she did in 2006.

Can you believe that some fashion critics weren't insanely in love with the elaborately feathered Atelier Versace Cruz wore in 2007? Neither can we.

The Aussie actress looked regal at the 2007 awards ceremony, wearing an ultra-glam Balenciaga gown that featured an oversized bow detail at the neck. Years later, fashion critics compared Kidman’s ensemble to a dress worn by Emma Stone at the 2012 Oscars.

She didn't score an Oscar in 2009, but Hathaway dominated the best dressed list in a dazzling ivory Giorgio Armani Prive mother-of-pearl stunner.

The Best Actress winner (for The Blind Side) absolutely wowed everyone in a shimmering gold beaded Marchesa gown, sleek hair and bright pink lips in 2010.

For her first Oscars in 2011 as a Best Actress nominee for Winter's Bone, Lawrence chose a jaw-dropping body-hugging Calvin Klein dress. "The more I learn about fashion, the more interesting it becomes," Lawrence later told USA Today.

Her Black Swan co-star Natalie Portman went home with an Oscar, but it was Kunis who killed it on the red carpet in a pale lilac Elie Saab Couture lace gown at the 2011 awards.

Adams went for a glam look in 2013 the custom Oscar de la Renta tulle and beaded gown. The high-fashion designer created the dress for Adams based on a photograph she presented as inspiration.

The Friends alum, who usually goes for black on the red carpet, really turned heads when she stepped out in a bright crimson-hued Valentino couture gown in 2013. The dramatic strapless dress featured a full skirt and a form-fitting bodice, which gave it an elegant fit-and-flare feel.

The Best Supporting Actress winner for 12 Years a Slave looked gorgeous in a powder blue silk pleated Prada gown featuring a deep V-neck bodice and low-cut sides in 2014. "It's a blue that reminds me of Nairobi," the Kenya-born star told Ryan Seacrest of her dress color. The Yale grad paired her look with a clutch and shoes, also by Prada, and a gold and diamond headband and jewels by Fred Leighton.

The Rock the Kasbah star looked gorgeous in a plunging neckline gown and matching cape by Atelier Versace. She paired the silver dress with Neil Lane Jewelry, including a ring, drop earrings and a diamond and sapphire bracelet. in 2014.

Stunning! Stone dazzled in a custom open-backed Elie Saab Haute Couture gown with a Lee Savage Clutch and Tiffany & Co. jewelry in 2015.

Going Wild for Reese! The actress accentuated her hourglass silhouette in a custom Tom Ford ice-blue gown with a black velvet border, paired with Jimmy Choo heels in 2015. She added sparkle with Tiffany & Co. jewelry.

The Brooklyn actress glowed in a glittering emerald Calvin Klein stunner with a semi-sheer skirt, teamed with mismatched drop earrings in 2016. 

The Danish Girl nominee channeled her inner Belle in a butter-yellow Louis Vuitton gown embellished with silver beading in 2016.

The Mindy Project creator and star stunned in a black Elizabeth Kennedy column dress, accented with a cornflower-blue bow train at the 2016 Oscars.

The How to Get Away with Murder star shined in a bright dress with shoulder cut-outs  by Armani Privé in 2017.

The Fargo actress channeled Grace Kelly in a black Christian Dior dress and a show-stopping diamond necklace at the 2017 Oscars.

The winner for Best Actress for La La Land reached for old-school Hollywood glamour in a Givenchy Haute Couture by Riccardo Tisci dress shimmery fringe in 2017.

The Best Supporting Actress winner stunned in a red Reem Acra dress with dramatically beautiful sleeves and $4 million Forevermark jewels at the 2018 awards. 

The Star Is Born actress channeled Audrey Hepburn in a black strapless Alexander McQueen gown with matching over-the-elbow gloves and Tiffany & Co. yellow diamonds for the 2019 Oscars.

The Room star dazzled at the 2019 awards show in a shimmering silver Celine mock-neck gown with Chanel jewelry and Jimmy Choo sandals.

The performer looked breathtaking at the 2020 Oscars in a custom Ralph Lauren gown that took over 600 hours to make. The designer embroidered the unmissable number with close to 170,000 Swarovski crystals.

The actress took home an Oscar at the 92nd annual awards ceremony on February 9, 2020, wearing a custom one-shoulder Armani Prive gown and Jimmy Choo pumps. The white sequined dress was easily deserving of an award of its own.

At the 2021 Academy Awards, the Malcolm & Marie actress wowed in a yellow Valentino gown, which she paired with more than $6 million of Bulgari jewelry.

In a custom Louis Vuitton gown embellished with sequins and crystals, the One Night in Miami director looked absolutely stunning at the 2021 Oscars. She accessorized her look with nearly $1.2 million of Forevermark jewelry. 

The Luckiest Girl Alive actress sported a rosy Zuhair Murad gown featuring a train cascading from her hip, strappy neckline and stunning diamond jewelry at the 2022 Oscars.

So pretty! The West Side Story star commanded attention in a sheer and sparkly Dior gown at the 2022 Academy Awards.

The “Happier Than Ever” singer looked ultra-glamorous at the 94th Awards Show in a staples Gucci number. The floor length frock was finished with black layers of ruffles which she teamed up with chunky rings and long white nails.

Beautiful in blue! The “Body” singer stunted a Gurav Gupta gown at the 2022 Oscars. The 3-D number featured a sweetheart neckline, cutout on her torso, and thigh high slit.

Elegant in emerald! The Matrix Resurrections star took our breath away at the 94th Annual Oscars in a Jean-Paul Gaultier dress. The gown was finished with ruffle details on the skirt and a long train.

The Eyes of Tammy Faye actress looked seriously stylish in an ombré Gucci getup at the 2022 Academy Awards. The garb started in a warm gold hue at the straps and faded into a sparkly lavender shade before finishing in beautiful ruffles.

The What’s Love Got to Do With It? star rocked a pastel pink Versace gown at the 2022 Oscars. The delicate outfit included floral details, a thigh-high slit and tulle details. She paired it with matching platform heels and a diamond necklace.

Slay! Zendaya charmed the 94th Annual Awards show in a silky Valentino crop top and silver sequined skirt. To spice up the look even more, she rocked her hair in a chic updo and added more bling to the ensemble with diamond bracelets from Bulgari.