The 28 best Oscars red carpet dresses of all time

Oscars red carpet dresses: the 28 best of all time

Credit: Getty Images

Fashion


The 28 best Oscars red carpet dresses of all time

By Lara Faye &Naomi May

3 years ago

3 min read

The Academy Awards’ red carpet has played host to the most gorgeous gowns in the world. From Cindy Crawford’s siren red dress to Billy Porter’s tuxedo gown, we’ve found the most stunning dresses in Oscars history. 

When it comes to award ceremonies, there’s nothing quite like the Oscars. Not only is it one of the most prestigious events in film, but the Academy Awards is also one of the biggest nights in the fashion calendar as Hollywood royalty bring our sartorial fantasies to life on the red carpet. Even against the backdrop of our increasingly tumultuous world, the Oscars red carpet still remains a magical moment of total escapism into the world of breathtaking gowns and high-octane glamour.

From Natalie Portman’s powerful tribute to female directors to thrift store vintage (here’s looking at you, Winona) every A-lister has brought their individual style to the Oscars since its inception in 1929. Now in its 94th year, we’ve seen more exquisite gowns than even the keenest celebrity style stalkers can remember. There’s been John Galliano suiting, Valentino couture – even a swan (yes, really.)

Ahead of this weekend’s in-person ceremony, we thought we’d refresh your memory with 28 of the best fashion moments from over the years, from Grace Kelly to Gwyneth Paltrow and everybody in between.

Best Oscars dresses: Janelle Monae in custom Ralph Lauren

Janelle Monáe in custom Ralph Lauren, 2020

Hand embroidered with 168,000 Swarovski crystals, Janelle Monáe’s stunning Ralph Lauren gown took an astounding 600 hours to make. The draped hooded detail pays homage to the model Grace Jones’ iconic look, while Janelle told Billy Porter that it was his custom Christian Siriano tuxedo gown from the 2019 ceremony that inspired her to go “all out” in this show-stopping masterpiece. 


Best Oscars dresses: Natalie Portman in Dior

Natalie Portman in Dior, 2020

Marrying elegance and subversion in one powerful look, Natalie Portman’s sensational Dior cape was embroidered with the names of female directors who were overlooked by the Academy at the 2020 Awards. Portman’s cape spotlighted snubbed female directors including Greta Gerwig, Lorene Scafaria and Lulu Wang


Best Oscars dresses: Sandra Oh in Elie Saab

Sandra Oh in Elie Saab, 2020

Cementing her status as red carpet royalty, Sandra Oh’s decadent champagne-coloured Elie Saab dress was a visual delight. Sculptural tulle sleeves, a sheer neckline, lashings of metallic sequins, a gold velvet belt and 3D effect tulle and lace applique may sound like too many elements, but they came together in perfect harmony in this ethereal gown. 


Best Oscars dresses: Jennifer Lopez in Zuhair Murad

Jennifer Lopez in Zuhair Murad, 2015

We can only imagine the hours of craftsmanship that went into this spectacular Zuhair Murad gown, but the true magic is Jennifer Lopez’s ability to wear this dress with such ease that it looks completely effortless. A devotee of the glamorous Lebanese label, J.Lo has worn Zuhair Murad’s dazzling creations both on and off stage, but this embellished gown remains one of her most iconic looks. 


Best Oscars dresses: Keira Knightley in Valentino

Keira Knightley in Valentino, 2015

The meticulous embroidery on Keira’s Valentino gown is simply breathtaking. Layering a hand-stitched botanical motif and handwritten script over layers of blush tulle, this dress feels like a fairy tale come to life. 


Best Oscars dresses: Kerry Washington in Atelier Versace

Kerry Washington in Atelier Versace, 2016

Versace has created some of the most iconic Oscars dresses of all time and Kerry Washington’s monochrome gown is no exception. The draped white skirting with thigh slit captured the spirit of old Hollywood glamour while the leather bodice felt completely futuristic. The overall effect? A totally contemporary take on red carpet couture. 


Best Oscars dresses: Grace Kelly in Edith Head

Grace Kelly in Edith Head, 1955

Is Grace Kelly the ultimate style icon? Unequivocally, yes. The spaghetti straps and ruched skirting make this sensational green dress feel so modern that it is hard to believe it was worn in 1955. Fashion fades, style truly is eternal. 


Best Oscars dresses: Emma Stone in Giambattista Valli

Emma Stone in Giambattista Valli, 2012

This rich jewel tone red is one the most evocative displays of colour we’ve ever seen at the Oscars. Where this top-to-toe block colour may have swamped some, this Giambattista Valli gown flattered Emma Stone’s frame with a nipped in waist and a tie halterneck. 


Best Oscars dresses: Lupita Nyong'o in Calvin Klein

Lupita Nyong’o in Calvin Klein, 2015

When it comes to the red carpet, Lupita Nyong’o can do no wrong. Though entire books could be written on her finest awards ceremony looks, the meticulously embellished bodice on this Calvin Klein dress makes it her most spectacular look yet. 


Best Oscars dresses: Gwyneth Paltrow in Ralph Lauren

Gwyneth Paltrow in Ralph Lauren, 1999

When Gwyneth won Best Actress for her role in Shakespeare In Love she took red carpet glamour and made it completely her own. This rose petal pink ball gown will go down in sartorial history as one of the most loved Oscars dresses of all time. 


Best Oscars dresses: Lady Gaga in Alaïa

Lady Gaga in Alaïa, 2015

Lady Gaga’s fearless fashion choices and natural affinity for dressing up makes her a joy to watch on the red carpet. While we’ll admit we don’t totally get the washing-up style gloves (you do you, Gaga!) we have never had more love for Gaga’s experimental approach to styling than when seeing her in this custom Alaïa gown. 


Best Oscars dresses: Gemma Chan in Valentino

Gemma Chan in Valentino, 2019

Gemma Chan single-handedly made red carpet dressing fun again in the most joyful Valentino gown we have ever had the pleasure to know. This simple silhouette feels fresh in an exuberant shade of pink and did we mention it has pockets? Yes, our ultimate style obsession, pockets. 


Best Oscars dresses: Halle Berry in Elie Saab

Halle Berry in Elie Saab, 2002

This embroidered Elie Saab gown made fashion history while Halle Berry made history as the first African-American woman to win an Oscar for Actress in a Leading Role. 


Best Oscars dresses: Elizabeth Hurley in Versace

Elizabeth Hurley in Versace, 1995

Liz Hurley’s glamorous aesthetic cemented her status as a style icon and this embellished Versace dress is arguably one of the most famous in the world. 


Best Oscars dresses: Billy Porter in Christian Siriano

Billy Porter in custom Christian Siriano, 2019

It’s suiting, but not as you know it. Billy Porter redefined the tuxedo and went down in red carpet history as he re-wrote the rule book and made menswear interesting again. 


Best Oscar dresses: Charlize Theron in Gucci

Charlize Theron in Gucci, 2004

The delicate pearl embellishments on this Gucci gown made Charlize look as though she had been draped in a sea of stars. This simple silhouette makes this dress a masterclass in the art of fit and cut. 


Best Oscars dresses: Cindy Crawford in Versace

Cindy Crawford in Versace, 1991

Cindy brought the red dress to the red carpet, and we’ve never looked back. The plunging bodice made headlines around the world and cemented Cindy’s status as a modern day siren. 


Best Oscars dresses: Beyonce in Versace

Beyonce in Versace, 2005

Beyonce redefined understated elegance in this black velvet Versace gown that seemed designed to temporarily stun our senses. 


Best Oscars dresses: Penelope Cruz in Atelier Versace

Penelope Cruz in Atelier Versace, 2007

From the swirling silk bodice to breathtaking skirt, every inch of this sumptuous Versace gown is a work of art. Penelope Cruz wears it with glittering diamond jewellery and intoxicating confidence. 


Best Oscars dresses: Celine Dion in John Galliano

Celine Dion in John Galliano, 1999

You say ‘dress’, Celine says ‘suit’. Celine took the rule book, tore it up and left everyone else wondering why they hadn’t thought of that as she stepped out in an exquisite John Galliano suit. 


Best Oscars dresses: Zoe Saldana in Givenchy

Zoe Saldana in Givenchy, 2010

No one has ever had as much fun on the red carpet as Zoe Saldana did in this Givenchy gown. Five tiers of purple ombre and a sparkling bodice made this strapless dress one of the most unforgettable Oscars looks of all time. 


Best Oscars dresses: Julia Roberts in vintage Valentino

Julia Roberts in vintage Valentino 2001

As we consider how to make the red carpet more sustainable, the A-list could learn a lot from Julia’s approach. She opted for a vintage Valentino gown when accepting her Oscar for Best Actress for her role in Erin Brockovich. 


Best Oscars dresses:Angelina Jolie in Marc Bouwer

Angelina Jolie in Marc Bouwer, 2004

A dress so iconic that it has its own Wikipedia page, this ivory satin dress paid homage to the styles of Rita Hayworth, Jean Harlow and Marilyn Monroe, yet felt completely Angelina. 


Best Oscars dresses: Nicole Kidman in Christian Dior

Nicole Kidman in Christian Dior, 1997

This exquisitely embroidered chinoiserie gown was the standout look of the 1997 Academy Awards. Nicole completed the look with a beaded handbag, filigree earrings and a statement lip for a bohemian take on awards ceremony elegance.


Best Oscars dresses: Bjork swan dress

Björk in Marjan Pejoski, 2001

No list of iconic Oscars looks would be complete without a tribute to the swan dress. Bjork showcased her eclectic style on the red carpet in one of the most memorable celebrity style moments of all time. 


Best Oscars dresses: Salma Hayek in Carolina Herreraerrera

Salma Hayek in Carolina Herrera, 2003

You can’t have a conversation about red carpet style without mentioning Carolina Herrera. The Venezuelan-born designer has dressed first ladies, royalty and Hollywood royalty alike. This monochrome gown showcases the sort of elegant simplicity that had made Carolina Herrera one of the world’s most influential designers, Salma makes it her own by adding just a single silver bangle for a look that is effortlessly elegant. 


Best Oscars dresses: Courtney Love in Versace

Courtney Love in Versace, 1997

Courtney Love might have her roots in grunge culture but at the 1997 Academy Awards she exuded pure Hollywood glamour in a classic off-white silk Versace dress. Courtney added a touch of her signature post-punk aesthetic with smokey black eyeliner and artfully smudged lipstick.


Best Oscars dresses: Winona Ryder in vintage

Winona Ryder in vintage, 1994

Legend has it that Winona Ryder bought this vintage beaded dress at a thrift store for just $10. We’re not one to spoil a good story but whether that’s true or mere fashion fable, Winona’s flapper-inspired look is simply sensational. 



Images: courtesy of Getty & Pinterest. 

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