The 11 Best Dresses In The History Of The Oscars

Ah, the Oscars - one of the biggest nights in film and fashion. Hollywood’s finest come out to shine every year, wearing some of the most breathtaking dresses imaginable. Since 1929, celebrities have wowed us with their fashion choices as they walk down that iconic red-carpeted aisle. 

The perfect Oscar gown isn’t a result of any one secret formula. From stylish silhouettes to bold colors and even glamorous embellishments, the key ingredient for creating an award-winning look is simply going with what looks best on you. That’s all it takes to make sure your outfit will be remembered as one of the night’s most memorable and fashionable choices!

As a fashion stylist, I have spent countless hours researching the most iconic and beautiful gowns from the Oscars past. So, without further ado, here are the 11 best dresses in the history of the Oscars. 

From Grace Kelly’s timeless classic in 1955 to Angelina Jolie’s elegance, these are some of the best looks ever to grace the red carpet. Get ready to be dazzled! 

11 Best Oscar Dresses Of All Time

If you are looking for an inspirational outfit for your birthday, wedding, or party, you can get some ideas from these Oscar-winning looks. Here are the 11 best dresses from Oscar history, from classic to modern. 

Grace Kelly in Edith Head, 1955

In 1955, Grace Kelly presented a spellbinding performance in The Country Girl. She graced the red carpet with an enchanting ice-blue gown from renowned costume designer Edith Head. 

Meticulously crafted from four thousand dollars worth of French satin, this premiere-worthy creation was complemented by a matching evening coat, ruby lips, and glamorous updo for the ultimate Hollywood look. 

Accentuating its graceful silhouette, this elegant floor-length gown features a back train and double thin spaghetti shoulder straps. The waistline is further accentuated by delicate ruffles that create the perfect finishing touch.

When she stepped onto the Oscar stage wearing the stunning blue gown, it made a lasting impression that will forever be remembered in Academy Awards history.

Gwyneth Paltrow in TOM FORD, 2012

In my ranking of likes, this particular outfit is one of the best in the history of the Oscars. Interestingly, it is consistently included in the list of the most beautiful star exits in the world top.

I love this white Gwyneth ensemble by Tom Ford for its incredible elegance, clean lines, and everything that makes it the epitome of minimalism at its best. However, I want to note that the triumph of Lupita Nyong’o in a similar outfit of bright red color was nothing but blatant plagiarism.

The dress is made of a single piece of white satin, which perfectly hugs and emphasizes the lines of Gwyneth’s body. The presence of a thin belt with a bow gives the image refinement and sophistication. 

Hilary Swank is Guy Laroche, 2005

My third favorite, who could also claim the top spot on the Oscars Best Dressed list. Hilary Swank won the second statuette of her career in 2005 for her role in Clint Eastwood’s Million Dollar Baby.

But it was not her only triumph on that momentous day — the choice of outfit for the red carpet impressed both fashion critics and fans of the star. That laconic dark blue Guy Laroche dress with an open back is still considered the most important fashion triumph in the history of the Oscars.

Chaste and sexy, deaf in front and very frank in the back, it turned the actress, who never claimed the title of a sex symbol, into a real star of the social chronicle. Long months of training for the role of a boxer did not go in vain - Hilary’s perfect back is still considered a benchmark.

Julia Roberts in Valentino, 2001

America’s favorite Julia Roberts was fully armed that fateful day - she not only won an Oscar for her role in the movie Erin Brockovich but also managed to choose an outfit that US fashion critics called the most elegant ever.

Everything genius turned out simple: Valentino’s black and white vintage outfit seemed incredibly simple and graphic, but the luxurious train added spice. But, of course, the actress’s role was no less important in creating an impressive look.

In a word, Julia showed a master class, which is still considered the highest aerobatics. The outfit surely deserved to be included in the Oscar best-dressed list.

Sandra Bullock in Marchesa, 2010

In 2010, Sandra Bullock won Best Actress of the year. And if there were a separate award for Best Dress at the Oscars, Sandra would take it. 

She was like an elegant golden statuette in a Marchesa dress, complemented by a simple hairstyle and bright red lipstick. Without a doubt, her retro look in the style of the golden age of Hollywood showed that timeless classics are always in fashion.

The top of the dress was adorned with many precious stones and sequins, making it even more attractive. The long dress was also complemented by an impressive train that gave the actress’s image a mystery.

Audrey Hepburn in Givenchy, 1954

A classic of the genre, Audrey is light, thin, and ringing in an elegant outfit of her favorite brand. Her love for Givenchy enriched the world with incomparable images in the gallery of the best outfits of the main style icon of the 20th century.

The dazzling white dress boasted a floral pattern and snugly-fitted belt, which proudly showcased Audrey Hepburn’s ultra-slender waistline. In addition, the ensemble featured an unusual boat neckline, extraordinary even for the red carpet of the Oscars!

Audrey’s look remains one of the best in awards ceremonies. It was light and airy but, at the same time, exquisite, mysterious, and feminine. The ensemble is a perfect example of how a movie star should look to be remembered in the history of cinema and fashion. 

Halle Berry in Elie Saab, 2002

Halle Berry became the main star of the Oscars in 2002! she not only received the cherished statuette that year but caused a real sensation, appearing in one of the sexiest outfits in the entire history of the Oscars red carpet.

A burgundy dress with a translucent bodice decorated with floral embroidery instantly made Lebanese designer Elie Saab the main couturier of bridal and evening fashion. 

The combination of the floor-length skirt, revealing neckline, and charming train made Halle Berry look like a real fairy! No wonder this image was immediately included in the list of best dresses in the history of the Oscars. 

The outfit inspired brides who still want to look like a real princess or queen on their wedding day. 

Nicole Kidman in Christian Dior, 1997

I miss that old Nicole, the redhead, not like everyone else, who has not yet turned into a cold blonde virgin, who is always commercially flawless. But, back in 1997, she took such bold and unusual steps that she broke the applause of all fashion critics. 

She wore a dress by John Galliano of complex green color with oriental motifs, which other Hollywood stars would never have dared to wear (they all chose completely safe black sheaths or classic women’s powder dresses made of chiffon), making a real sensation.

W magazine lauded the dress, calling it a “milestone for both designer and wearer.” After John Galliano was appointed as Dior’s new creative director in the fall of that year, Nicole Kidman donning his design at the Oscars indicated his imminent success on red carpets worldwide.

Sharon Stone in the Gap and Vera Wang, 1998

Fashion critics were very surprised by Sharon Stone, who appeared on the red carpet of the Oscars in 1998 in a casual style. With a lilac Vera Wong skirt, she matched a simple white Gap shirt, which, by her admission, she borrowed from her then-husband, Phil Bronte. 

The bold move was rare when a star dressed outside the dress code became an example of good taste. Sharon Stone’s outfit was both out of the ordinary and very elegant, proving that you don’t have to splurge on a designer dress to look chic and fashionable.

This unexpected decision from Stone became an example for many stars who wanted to break the rules while looking at the ceremony following its dress code.

Reese Witherspoon in Nina Ricci, 2007

Reese phenomenally succeeded in making the simple complex and the complex simple. Girly bangs, loose hair, a big smile — and this girl-next-door image is suddenly complemented by silk ruffles from Nina Ricci.

With such a cut and color, this dress could be elevated in the image of a virgin and lost in it! For a fresh take on the classic, Reese earns her place of honor in ranking the best outfits in the history of the Oscars.

The choice of Reese was praised by fashion critics, who noted that the actress combined femininity and charm with elegance. The dress was simple and elegant, and the bow at the back made it even more special!

Angelina Jole in Atelier Versace, 2012

Finally, Angelina Jolie’s black Versace gown at the 2012 Oscars deserves special mention. The breathtaking, deep velvet gown was a masterpiece, enhancing Angelina Jolie’s beauty. It featured elaborate neckline ruffles, a bustle, two diamond clips adorning an asymmetrical bodice, and an eye-catching thigh-high slit.

She topped the look off with classic yet sophisticated accessories such as a voluminous wavy hairstyle, red lipstick by Neil Lane Jewelry, and a Jaime Mascaro clutch and Salvatore Ferragamo peep-toe platform heels.

Angelina Jolie’s outfit became a real symbol of elegance and sophistication. She looked like a goddess, and the audience was stunned at her beauty!

Bottom Line

Over the years, we have seen some truly inspiring and memorable red carpet moments at the Academy Awards. 

From Nicole Kidman’s bold choices to Sharon Stone’s unexpected take on a classic style to Reese Witherspoon’s girly and elegant look to Angelina Jolie’s breathtaking Atelier Versace gown - all of these iconic looks showed us how to take risks with fashion while still looking sophisticated and chic. 

Each of these actresses made a lasting impression on the red carpet, showing us all that true style never goes out of fashion!