Fashion

The 28 most iconic Oscars dresses of all time

Posted by
Lara Faye
Published
backgroundLayer 1
Add this article to your list of favourites
Best Oscars dresses: Sandra Oh

The most glamorous night in film, 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 awards ceremonies, there’s nothing quite like the Oscars. Not just one of the most prestigious events in film, the Academy Awards is one the biggest nights in fashion as Hollywood royalty bring our fashion 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.

You may also like

Oscars 2020: everything you need to know about this year’s Academy Awards

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. Now in their 92nd year, we’ve seen more exquisite gowns than even the keenest celebrity style stalkers can remember. We’ve seen John Galliano suiting, Valentino couture – even a swan. Now the Stylist fashion team is here to refresh your memory with all the celebrity fashion moments that defined the Oscars. 

  • Janelle Monae in custom Ralph Lauren, 2020

    Best Oscars dresses: Janelle Monae in custom Ralph Lauren
    Best Oscars dresses: Janelle Monae in custom Ralph Lauren

    Hand embroidered with 168,000 Swarovski crystals, Janelle Monae’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. 

  • Natalie Portman in Dior, 2020

    Best Oscars dresses: Natalie Portman in Dior
    Best Oscars dresses: Natalie Portman in Dior

    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

  • Sandra Oh in Elie Saab, 2020

    Best Oscars dresses: Sandra Oh in Elie Saab
    Best Oscars dresses: Sandra Oh in Elie Saab

    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. 

  • Jennifer Lopez in Zuhair Murad, 2015

    Best Oscars dresses: Jennifer Lopez in Zuhair Murad
    Best Oscars dresses: Jennifer Lopez in Zuhair Murad,

    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. 

  • Keira Knightley in Valentino, 2015

    Best Oscars dresses: Keira Knightley in Valentino
    Best Oscars dresses: Keira Knightley in Valentino

    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. 

  • Kerry Washington in Atelier Versace, 2016

    Best Oscars dresses: Kerry Washington in Atelier Versace
    Best Oscars dresses: Kerry Washington in Atelier Versace

     Versace have 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. 

  • Grace Kelly in Edith Head, 1955

    Best Oscars dresses: Grace Kelly in Edith Head
    Best Oscars dresses: Grace Kelly in Edith Head

    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. 

  • Emma Stone in Giambattista Valli, 2012

    Best Oscars dresses: Emma Stone in Giambattista Valli
    Best Oscars dresses: Emma Stone in Giambattista Valli

    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. 

  • Lupita Nyong’o in Calvin Klein, 2015

    Best Oscars dresses: Lupita Nyong'o in Calvin Klein
    Best Oscars dresses: Lupita Nyong'o in Calvin Klein

    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 make it her most spectacular look yet. 

  • Gwyneth Paltrow in Ralph Lauren, 1999

    Best Oscars dresses: Gwyneth Paltrow in Ralph Lauren
    Best Oscars dresses: Gwyneth Paltrow in Ralph Lauren

    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. 

  • Lady Gaga in Alaïa, 2015

    Best Oscars dresses: Lady Gaga in Alaïa
    Lady Gaga has released her new song Stupid Love, and it's going to be the top tune of 2020.

    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. 

  • Gemma Chan in Valentino, 2019

    Best Oscars dresses: Gemma Chan in Valentino
    Best Oscars dresses: Gemma Chan in Valentino

    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. 

  • Halle Berry in Elie Saab, 2002

    Best Oscars dresses: Halle Berry in Elie Saab
    Best Oscars dresses: Halle Berry in Elie Saab

    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. 

  • Elizabeth Hurley in Versace, 1995

    Best Oscars dresses: Elizabeth Hurley in Versace
    Best Oscars dresses: Elizabeth Hurley in Versace

    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. 

  • Billy Porter in custom Christian Siriano, 2019

    Best Oscars dresses: Billy Porter in Christian Siriano

    Cinderella remake: Billy Porter will play Fairy Godmother

    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. 

  • Charlize Theron in Gucci, 2004

    Best Oscar dresses: Charlize Theron in Gucci
    Charlize Theron is keen to put baseless romance rumours to bed.

    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. 

  • Cindy Crawford in Versace, 1991

    Best Oscars dresses: Cindy Crawford in Versace
    Best Oscars dresses: Cindy Crawford in Versace

    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. 

  • Beyonce in Versace, 2005

    Best Oscars dresses: Beyonce in Versace
    Best Oscars dresses: Beyonce in Versace

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

  • Penelope Cruz in Atelier Versace, 2007

    Best Oscars dresses: Penelope Cruz in Atelier Versace
    Best Oscars dresses: Penelope Cruz in Atelier Versace

    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. 

  • Celine Dion in John Galliano, 1999

    Best Oscars dresses: Celine Dion in John Galliano
    Best Oscars dresses: Celine Dion in John Galliano

    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. 

  • Zoe Saldana in Givenchy, 2010

    Best Oscars dresses: Zoe Saldana in Givenchy
    Best Oscars dresses: Zoe Saldana in Givenchy

    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. 

  • Julia Roberts in vintage Valentino 2001

    Best Oscars dresses: Julia Roberts in vintage Valentino
    Best Oscars dresses: Julia Roberts in vintage Valentino

    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. 

  • Angelina Jolie in Marc Bouwer, 2004

    Best Oscars dresses:Angelina Jolie in Marc Bouwer
    Best Oscars dresses: Angelina Jolie in Marc Bouwer

    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. 

  • Nicole Kidman in Christian Dior, 1997

    Best Oscars dresses: Nicole Kidman in Christian Dior
    Best Oscars dresses: Nicole Kidman in Christian Dior

    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.

  • Björk in Marjan Pejoski, 2001

    Best Oscars dresses: Bjork swan dress
    Best Oscars dresses: Bjork swan dress

    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. 

  • Salma Hayek in Carolina Herrera, 2003

    Best Oscars dresses: Salma Hayek in Carolina Herreraerrera
    Best Oscars dresses: Salma Hayek in Carolina Herrera

    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. 

  • Courtney Love in Versace, 1997

    Best Oscars dresses: Courtney Love in Versace
    Best Oscars dresses: Courtney Love in Versace

    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.

  • Winona Ryder in vintage, 1994

    Best Oscars dresses: Winona Ryder in vintage
    Best Oscars dresses: Winona Ryder in vintage

    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. 

  • Best Oscars dresses: Sandra Oh in Elie Saab
    Best Oscars dresses: Sandra Oh in Elie Saab

Sign up for our essential edit of what to buy, see, read and do, and also receive our 11-page Ultimate Guide To Making Your Home Feel Bigger.

By entering my email I agree to Stylist’s Privacy Policy

Images: courtesy of Getty & Pinterest. 

Topics

Share this article

Author

Lara Faye

Recommended by Lara Faye

Fashion

Baftas 2020: standout fashion moments from the red carpet

Sustainable fashion ruled the waves on the biggest night of the British film calendar.

Posted by
Anna Brech
Published
Fashion

Golden Globes 2020: see all your favourite celebrities on the red carpet

From Greta Gerwig to Phoebe Waller-Bridge, see the biggest stars arrive at one of Hollywood's most glamorous nights.

Posted by
Hannah-Rose Yee
Published
Fashion

Grammys 2020: all the best looks from the red carpet

From Ariana Grande and Lizzo's glamorous gowns to Billy Porter's motorised hat, here are the most show-stopping outfits from the 62nd Annual Grammy Awards.

Posted by
Ally Sinyard
Published
Fashion

Critics’ Choice Awards 2020: standout fashion moments from the red carpet

Catch up on all the highlights, as the great and the good descend on Santa Monica.

Posted by
Anna Brech
Published