top of page

The 10 most iconic Oscars outfits of all time

As Hollywood gears up for the 2024 Oscars, we rewind the glamour clock to showcase the unforgettable moments that unfolded on the red carpet

With the anticipation building for the upcoming Oscars, we revisit the mesmerising fashion statements that have graced the red carpet over the years. From timeless classics to daring avant-garde creations, these 10 iconic outfits have not only defined the pinnacle of elegance but have also become synonymous with the glitz and glamour of Hollywood's most prestigious night.

Grace Kelly in Edith Head, 1955

Grace Kelly claimed her Oscar for The Country Girl draped in a pristine ice-blue creation crafted by the legendary Edith Head, who described the hue as "blue Champagne". It was created for the film's premiere four months ago, with Kelly donning a matching evening coat on that night. The gown was meticulously tailored from a lavish French satin (priced at US$4,000) and cemented Kelly's status as an enduring symbol of red carpet sophistication.

Elizabeth Taylor in Christian Dior, 1961

Adorned with intricate floral embroidery and a bold crimson silk bloom at the waist, Elizabeth Taylor graced the 33rd Academy Awards in a captivating Christian Dior gown. This dress, worn on the night of her first Oscars win, became a cherished symbol of luck for Taylor. Although never worn in public again, the gown accompanied her on travels as her "lucky charm". Initially presumed to have returned to the Christian Dior archive in Paris after Taylor's passing, it was, in fact, recently unearthed from one of the star's long-forgotten suitcases. It is set to be auctioned soon, with expectations of fetching up to an impressive US$73,000.

Barbra Streisand in Arnold Scaasi, 1969

For the inaugural televised Academy Awards in 1969, Barbra Streisand made a bold statement in an unforgettable sequined pyjama pantsuit crafted by Arnold Scaasi.

Presented with two elegant yet conservative dresses before the show, Streisand opted for a daring departure – a pantsuit featuring flared legs, tuxedo cuffs and plastic sequins.

The ensemble's contrasting collar, bow, cuffs and sheer elements marked it as a strikingly modern option for its time. But her unconventional choice proved serendipitous, as she clinched the award that year for Funny Girl, tying with Katherine Hepburn for The Lion in Winter.

Cher in Bob Mackie, 1986

It wasn't the first time that Cher wore a Bob Mackie creation to the Academy Awards (and it wouldn't be the last either), but the star's 1986 outfit designed by the American costumier became the talk of the town for various reasons. Despite hoping for a nomination for Mask and facing disappointment, Cher defied convention. Rather than resigning to the snub, she seized control of her narrative and graced the event in a show-stopping ensemble, fearlessly claiming the spotlight and making a memorable statement.

Dressed in a showgirl-inspired costume, Cher made an entrance with a towering feathered headdress and a midriff-baring outfit featuring triangular hems on both the top and bottom. The look sparked mixed reactions, and the designer later revealed that the creation was, in part, a response to Cher's Oscars snub – her very own "revenge dress"

Gwyneth Paltrow in Ralph Lauren, 1999, and in Tom Ford, 2012

The Oscar-winning actress graced the red carpet with not one but two iconic outfits. Her bubblegum pink taffeta gown at the 71st Academy Awards in 1999 remains a topic of conversation, drawing comparisons to Grace Kelly's style for its timeless elegance. This memorable night saw her claim the Best Actress award for Shakespeare In Love. Over a decade later, in 2012, Paltrow made another striking appearance, donning a white floor-length Tom Ford dress with a chic cape. Fashion critics unanimously declared it one of the best Oscar dresses of all time – and it also served as a first public preview of the highly anticipated Fall/Winter line from the American designer.

Halle Berry in Elie Saab, 2002

In 2002, Halle Berry became the first Black woman to win a Best Actress Oscar for her role in Monster's Ball. Complementing this history-making moment was an equally iconic gown by Elie Saab. The dress featured a semi-sheer ensemble with a mesh bodice adorned by delicate floral appliqués, and a deep red, asymmetrical taffeta skirt. This iconic gown is now on display at the Academy Museum of Motion Pictures.

Hilary Swank in Guy Laroche, 2005

While fellow stars embraced off-the-shoulder or strapless styles at the 2005 Oscars, Hilary Swank made one of the boldest fashion statements on the night she won the Best Actress Award for her role in Million Dollar Baby. Opting for a high-neck, sapphire-blue gown with form-fitting long sleeves that accentuated her curves, Swank added an audacious touch with a completely bare back. Keeping the overall look understated, she opted for minimal makeup, a pair of elegant diamond earrings and a black clutch, allowing the dress to rightfully claim the spotlight as the true attention-stealer of the evening.

Nicole Kidman in Balenciaga, 2007

Nicole Kidman, known for her chic style throughout her Hollywood career, etched an unforgettable fashion moment at the 2007 Oscars. Dressed in a radiant scarlet gown by Balenciaga, Kidman's ensemble featured a striking floor-trailing bow tied at the neck, creating a sculptural masterpiece. Her look was impeccably styled, with sleek, straight strawberry-blonde hair and a classic crimson lipstick. Accessories remained minimal, showcasing elegance with just a sparkling diamond bracelet adorning each wrist.

Angelina Jolie in Versace, 2012

It's the look that broke the Internet the night following the 2012 Oscars, as Angelina Jolie famously showed off her right leg in a striking black Versace gown. The actress initially turned heads on the red carpet and continued to make waves when she stepped onstage to present the award for Best Adapted Screenplay. The memorable moment went viral after Alexander Payne, Nat Faxon and Jim Rash, accepting for The Descendants, playfully emulated Jolie's iconic pose. By the end of the night, this show-stopping moment had gone viral. Not only did it solidify the dress as one of the most memorable pieces in fashion history, but Jolie's pose transcended the red carpet, becoming a significant and enduring moment in pop culture.

Lupita Nyong'o in Prada, 2014

Lupita Nyong'o's custom Prada gown, worn at the 2014 Oscars – the night she won the Academy Award for Best Supporting Actress for her performance in 12 Years a Slave – is an elegantly understated masterpiece. The powder blue pleated silk design, featuring a low-cut front and back, appears deceptively simple at first glance. But a closer look unveils subtle crystal details adorning the edges of the skirt's pleats, delicately catching the light without overwhelming the overall aesthetic.


bottom of page