When it comes to red carpet fashion, the Oscars are like the Super Bowl and the World Series rolled into one. Celebs bring their A game when it comes to Oscar dresses. Always looking to score a MVP slot for the evening and possibly in the hallowed halls of history. (OK, that’s all our sports knowledge!)
So what does it take to stand out among such well-dressed company? Over the years we’ve learned that risk frequently equals reward. And sometimes simplicity is key. Check out the best of the best from Oscar ceremonies gone by above to get primed to watch this year’s telecast and see how the latest attendees fare on the fashion front.
Oscars Greatest Hits The 39 Best Gowns to Ever Grace the Red Carpet
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Audrey Hepburn, 1954
This floral gown crafted by Hubert de Givenchy was everything you’d expect an Audrey Hepburn look to be; charming, elegant and unforgettable.
Image: Getty
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Grace Kelly, 1955
It was the pale blue hue of Grace Kelly’s Edith Head gown that really made an impression.
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Elizabeth Taylor, 1961
Christian Dior’s gown with yellow bodice and floral patterned skirt was fit for a queen, or in this case, a Dame.
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Farrah Fawcett, 1978
Sure, it reminds us of disco now, but back in 1978, the Charlie's Angels star shined in a cutting edge Stephen Burrows gold chain-mail dress.
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Cindy Crawford, 1991
Cindy Crawford took the plunge in a red hot Versace.
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Nicole Kidman, 1997
Nicole Kidman’s Asian-style chartreuse Christian Dior gown is one of the reasons we have fond memories of John Galliano’s time at the brand.
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Courtney Love, 1997
We were all shocked how well Courtney Love cleaned up in this white satin Versace gown.
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Gwyneth Paltrow, 1999
While this Ralph Lauren creation received pretty mixed reactions, its sublime structure and pink color made it a winner.
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Julia Roberts, 2001
Julia Roberts went vintage in a black and white Valentino gown from 1982 and made us realize that not everything from that decade qualifies as a fashion travesty.
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Renée Zellweger, 2001
Renée Zellweger brightened up the red carpet in a classic Jean Dessès yellow strapless gown.
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Halle Berry, 2002
Halle Berry’s Elie Saab embroidered gown with satin train was just as epic as the star’s acceptance speech during the awards.
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Kate Winslet, 2002
Little known designer Ben de Lisi made a name for himself when Kate Winslet stepped out in this red gown with a floral-covered strap.
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Kate Hudson, 2003
The epitome of Old School glamour in Versace.
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Jennifer Lopez, 2003
A covered up Jennifer Lopez made just as much of an impact in Valentino as she did in that daring Versace at the Grammys.
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Julianne Moore, 2003
Julianne Moore left fellow red carpet brethren green with jealousy courtesy of her strapless Tom Ford for Yves Saint Laurent ruffled gown.
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Charlize Theron, 2004
Looking like she could have been a transplant from the 20s, Charlize Theron took home the gold in an embellished backless Gucci.
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Angelina Jolie, 2004
Angelina Jolie’s white Marc Bouwer satin gown was minimalism at its finest.
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Hilary Swank, 2005
Bringing sexy back in Guy Laroche.
Image: Jody Cortes/WENN
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Beyoncé, 2005
Beyoncé cut a striking silhouette in a black velvet vintage Versace gown.
Image: Jody Cortes/WENN
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Michelle Williams, 2006
Michelle Williams looked marvelous in a marigold Vera Wang gown, punctuated by a strong red lip.
Image: Nikki Nelson / WENN
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Keira Knightley, 2006
Keira Knightley’s plum Vera Wang one-shoulder gown featured a fantastically sculpted mermaid skirt.
Image: Nikki Nelson / WENN
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Nicole Kidman, 2007
The Oscar winner delivered another show-stopping moment decked out in this fiery Balenciaga gown with a statement-making bow detail.
Image: Nikki Nelson/ WENN
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Penélope Cruz, 2007
From the texture up top to the flock of feathers on the bottom, this blush Atelier Versace had it all.
Image: Nikki Nelson/ WENN
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Marion Cotillard, 2008
Jean Paul Gaultier’s ivory fishtail gown tipped the fashion scales in the then relatively unknown French actress’ favor.
Image: Starbux / WENN
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Anne Hathaway, 2009
Armani Privé proved that sometimes sparkle is all you need.
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Freida Pinto, 2009
Freida Pinto’s beautiful blue John Galliano creation wouldn’t have been nearly as enticing without that solitary embellished sheer sleeve.
Image: Starbux / WENN.com
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Sandra Bullock, 2010
The only thing that could compete with Sandra Bullock’s ornate Marchesa gown was an Oscar statue.
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Zoe Saldana, 2010
A purple Givenchy Haute Couture gown with an ombre skirt, need we say more?
Image: Adriana M. Barraza / WENN
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Cate Blanchett, 2011
Cate Blanchett commanded attention in this armor-like lilac Givenchy Haute Couture pleated chiffon gown with tonal and yellow pearl accents.
Image: Ian Wilson/WENN.com
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Mila Kunis, 2011
Mila Kunis' lavish lavender Elie Saab Haute Couture gown replete with lace was picture perfect.
Image: Adriana M. Barraza / WENN.com
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Jennifer Lawrence, 2011
She’s had many Oscar outings, but this stunning scarlet dress by Calvin Klein created a real look-at-me moment.
Image: Adriana M. Barraza/WENN.com
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Gwyneth Paltrow, 2012
The caped crusader worked this sleek Tom Ford number.
Image: Adriana M. Barraza/ WENN.com
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Octavia Spencer, 2012
Octavia Spencer plus Tadashi Shoji equals outstanding.
Image: Adriana M. Barraza/WENN.com
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Michelle Williams, 2012
Michelle captivated in a coral Louis Vuitton strapless gown with a bow-accented peplum.
Image: Adriana M. Barraza/WENN.com
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Emma Stone, 2012
You know a gown is gorgeous when it can be compared to someone else's look (Nicole’s eye-catching Balenciaga from 2007) and still receive rave reviews like Emma Stone’s Giambattista Valli Haute Couture creation.
Image: Adriana M. Barraza/ WENN.com
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Kerry Washington, 2013
Between the elaborate bodice and the vibrant shade, there was a lot to love about Kerry Washington's Miu Miu gown.
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Amy Adams, 2013
An Oscar-worthy custom piece from Oscar de la Renta.
Image: WENN.com
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Lupita Nyong'o, 2014
The fashion community anticipated big things from Lupita Nyong'o on Oscar night and boy did she meet expectations in this baby blue pleated Prada gown.
Image: Adriana M. Barraza/WENN.com
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Cate Blanchett, 2014
Cate’s Armani Privé was deliciously luxe thanks to a mix of embellishments, embroidery and tulle.
Image: Adriana M. Barraza/WENN.com
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Lupita Nyong'o, 2015
Lupita’s custom Calvin Klein Collection gown was comprised of 6,000 pearls and paired with pearl-accented Nicholas Kirkwood heels. The gown also managed to grab headlines after being stolen from her hotel room just days after the ceremony, but luckily the pricey piece was discovered in a bathroom in another part of the hotel just two days after it disappeared.
Image: Jason Merritt/Getty Images
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Rita Ora, 2015
Rita Ora loves to shock on the red carpet and we were certainly taken aback by her look at the 2015 Oscars. The singer captured the spotlight for all the right reasons in this gorgeous dark blue Marchesa gown punctuated by gold leaf embroidery, which was styled with equally eye-catching Bulgari and Lorraine Schwartz jewelry.
Image: Dan MacMedan/WireImage
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Emma Stone, 2015
Emma famously suffered a wardrobe malfunction in this dazzling slit-to-there Elie Saab Haute Couture chartreuse gown. Complementary Christian Louboutin sandals and a textured side-parted ‘do helped make this look one of the night’s most memorable.
Image: Adriana M. Barraza/WENN.com
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Rosamund Pike, 2015
It was the lacy embroidery on Rosamund Pike’s red Givenchy Haute Couture strapless gown that really made an impression. A daring center slit was the perfect way to showcase those matching ankle-strap sandals.
Image: Jason Merritt/Getty Images
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Jennifer Lopez, 2015
We’re used to seeing Jennifer decked out in figure-hugging fare, so this princess-like Elie Saab Haute Couture Fall 2014 nude embroidered gown was a bit of a departure. That plunging neckline still provided a healthy dose of sex appeal, though.
Image: WENN.com
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Scarlett Johansson, 2015
Scarlett Johansson’s emerald Atelier Versace custom gown featured a scene-stealing collar embroidered with Swarovski crystals. Her slicked-back hairstyle ensured all eyes would be focused on that brilliant neckline.
Image: Adriana M. Barraza/WENN.com
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Viola Davis, 2015
Viola Davis’ pale Zac Posen off-the-shoulder gown with layered skirt fit the actress like a dream. Her Van Cleef & Arpels Valadon necklace perfectly polished off the look.
Image: Apega/WENN.com
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Cate Blanchett, 2016
Cate Blanchett’s dazzling seafoam green Armani Privé cap-sleeve gown came complete with white feathers and Swarovski crystals, making it one memorable dress. A perfectly coordinated Roger Vivier clutch and Tiffany & Co. jewelry finished things off with a bang.
Image: Kevin Mazur/WireImage/Getty Images
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Charlize Theron, 2016
Bringing the drama in a fiery Christian Dior plunging gown, Charlize Theron topped off the stunner with a scene-stealing diamond Harry Winston necklace.
Image: Dan MacMedan/WireImage/Getty Images
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Naomi Watts, 2016
This colorful ombre Armani Privé guaranteed Naomi Watts would stand out on the red carpet. Her impressive sparkling Bulgari diamond necklace didn’t hurt, either.
Image: Jason Merritt/Getty Images
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Lady Gaga, 2016
Is it a jumpsuit or a gown? It’s actually both and Lady Gaga’s daring white Brandon Maxwell strapless creation was a fashion risk that paid off in spades.
Image: Ethan Miller/Getty Images
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Janelle Monáe, 2017
Janelle Monáe really stole the spotlight in this ornate Elie Saab haute couture gown.
Image: Steve Granitz/WireImage/Getty Images
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Zendaya, 2018
Zendaya's chocolate brown Giambattista Valli haute couture gown was both simple and stunning.
Image: Kevin Mazur/WireImage/Getty Images
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Jennifer Garner, 2018
Jennifer Garner's electric blue Atelier Versace brought plenty of drama to the red carpet.
Image: Jeff Kravitz/FilmMagic/Getty Images
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Billy Porter, 2019
The Pose star's hybrid Christian Siriano tuxedo dress was pretty fierce.
Image: Dan MacMedan/Getty Images
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Jennifer Lopez, 2019
She may not have earned a nomination this year, but Jennifer Lopez wowed last year decked out in this flashy Tom Ford stunner.
Image: Jeff Kravitz/FilmMagic/Getty Images
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Scarlett Johansson, 2020
The structured, fringed bodice on this Oscar de la Renta was everything.
Image: Amy Sussman/Getty Images
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Janelle Monáe, 2020
This hooded Ralph Lauren Collection creation was a real showstopper.
Image: Amy Sussman/Getty Images
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Amanda Seyfried, 2021
Amanda Seyfried really took the plunge with this red pleated Armani Privé gown.
Image: ABC via Getty Images
