It’s that time of year again. Every week there’s an award show on TV, but this coming Sunday is the culmination of all the awards, the 89th Academy Awards. Many people find the over 3 hour award show a tad tedious, but no one can deny that the parade of designer dresses as anything short of spectacular. Even if you don’t watch the show on Sunday you know you’ll be searching for “Best Dressed” come Monday morning.
We’ve decided to go through decades of gowns to put together our favourite dresses from the past 89 years. Though there are WAY too many favourites to list here, we’ve narrowed it down to the top 20.
1. Audrey Hepburn, 1954, Givenchy
In 1954 Audrey Hepburn won the Oscar for Best Actress in Roman Holiday. She stole the show in her white belted floral Givenchy dress. The actress and Hubert de Givenchy developed a close friendship after meeting during the filming of Sabrina. This classic dress definitely deserves to be on our list of the top Oscar dresses. It’s even been voted as the greatest Oscar dress of all time. Audrey was always a classy lady and her choice of outfit for Hollywood’s biggest night was no different.
2. Grace Kelly, 1955, Edith Head
Edith Head was a costumier at Paramount when she designed this mint green gown for Grace Kelly to wear to the premiere of The Country Girl. The actress later wore the gown to the Oscars where she won the award for Best Actress in The Country Girl. This gown just proves that Grace Kelly was a style icon.
3. Farrah Fawcett, 1978, Stephen Burrows
Farrah Fawcett + sexy, skimpy gold dress = SEX SYMBOL. There’s no denying that Farrah Fawcett knew how to turn heads. Oh how we wish we could pull off that dress or that hair.
5. Nicole Kidman, 1997, Dior
Nicole Kidman may have changed fashion on the red carpet for good when she showed up in this bright yellow silk gown. The shocking colour was one thing, but no wrinkles…now that’s impressive.
4. Gwyneth Paltrow, 1999, Ralph Lauren
Gwyneth Paltrow set herself apart as a style icon with this pink princess dress at the 1999 Academy Awards. The actress won the Oscar for Best Actress in Shakespeare in Love and we fell in love with her style. The actress revealed to People.com that she hopes her daughter will wear this dress to her Prom. Coolest mom ever!
6. Halle Berry, 2002, Elie Saab
Halle Berry wore this sheer Adam and Eve style Elie Saab dress that just covered up the essentials the night she became the first African American woman to win Best Actress at the Academy Awards. At the time this was a risky dress to wear to the Oscars, but we think it’s the perfect gown to break barriers.
7. Kate Winslet, 2002, Ben De Lisi
Red dresses are nothing new to the Oscars red carpet, but this one shoulder Ben De Lisi gown is perfection. The flowery strap added a bit of detail to the simple yet ultra-glamourous gown.
8. Reese Witherspoon, 2006, Christian Dior
Reese Witherspoon found this 1955 Dior gown while shopping in a vintage boutique in Paris. The V neck gown with metallic embellishments was part of Reese’s magical night when she won Best Actress in Walk the Line. The actress says she’s stored the gown away and won’t ever wear it again. “It was a moment in time,” she explained to InStyle.
9. Michelle Williams, 2006, Vera Wang
Its hard to pull off yellow, especially while standing on a red carpet, but Michelle Williams did just that in 2006 when she wore this fluted yellow Vera Wang dress. And the actress made it look effortless.
10. Nicole Kidman, 2007, Balenciaga
Nicole Kidman…again. This actress is anything but ordinary. She received some backlash for wearing a giant bow on her neck in 2007, but we think the trailing bow puts a modern twist on this timeless gown.
11. Sandra Bullock, 2010, Marchesa
The simmering silver beaded gown of Sandra Bullock’s 2010 Oscar gown was the epitome of glamour. This dress is everything Hollywood’s biggest night represents: elegance, opulence and sparkle. Sandra Bullock wore this Marchesa gown when she won Best Actress in The Blind Side.
12. Zoe Saldana, 2010, Givenchy
From the sparkling bodice to the billowing ombré skirt we love everything about this dress. Zoe Saldana was eye-catching in this bold Givenchy dress with it’s layers of floating tulle and dramatic colours. This gown is just plain fun.
13. Mila Kunis, 2011, Elie Saab
Beautiful, light and feminine are just a few choice words we’d use to describe the lilac and lace Elie Saab dress Mila Kunis wore to the 2011 Academy Awards.
14. Cate Blanchett, 2011, Givenchy
Critics are split on Cate Blanchett’s choice of gown for the 2011 Academy Awards. But for us, this Givenchy gown is one of the best. It is simple and yet risqué. The bead work and square sleeves added detail and structure, while the delicate lilac colour added elegance. Maybe Cate didn’t win Best Actress, but she won “Best Dressed” according to us.
15. Angelina Jolie, 2012, Atelier Versace
Never skip leg day! Although Angelina Jolie has been mocked for her awkward “attention-seeking” stance on the red carpet, we think the black gown with the thigh high slit was a showstopper and not just because of the viral sensation Angie’s right leg sparked.
16. Gwyneth Paltrow, 2012, Tom Ford
If this dress doesn’t scream “powerhouse” we don’t know what does. The always elegant and stylish Gwyneth Paltrow turned heads at the 2012 Oscars with this all white Tom Ford gown. We say bravo because two minutes on us and it would already have a stain.
17. Amy Adams, 2013, Oscar de la Renta
The idea for this gown started with a black and white photograph of a model walking into a doorway. The actress worked with Oscar de la Renta on the design for the dress, bringing with her photographs to inspire the designer. And we say it definitely paid off, this silver-blue tulle and beaded gown was a hit. Adams looked like Princess Giselle in real life.
18. Lupita Nyong’o, 2014, Prada
The 12 Years a Slave star brought ethereal beauty to the Oscars red carpet in 2014. The pale blue silk Prada dress with it’s plunging neckline and flowing skirt shot Lupita to style stardom. “It’s a blue that reminds me of Nairobi, so I wanted to have a little bit of home,” she explained to Ryan Seacrest on the red carpet.
19. Rosamund Pike, 2015, Givenchy
Rosemund Pike looked the part of a beautiful English Rose in this strapless red embroidered Givenchy gown. The Gone Girl actress balanced grace and class with that racy leg slit. If only her character in Gone Girl had the same poise.
20. Brie Larson, 2016, Gucci
All eyes were on Brie Larson as the favourite to win Best Actress for her performance in Room at the 2016 Academy Awards. The actress didn’t disappoint in her choice of gown. We love the colour choice and the ornate belt with ruffled skirt is striking while remaining classic. Brie took home the Oscar and “Best Dressed” that night.
The 89th Academy Awards are on Sunday, February 26th. We can’t wait to see who will be “Best Dressed” this year!
Written by Sonya Davidson