Red carpet attire gives actors an opportunity to express a different side of themselves. My way of measuring how unforgettable a dress involves a combination of factors: Does the dress have a wow factor? Do the hair, makeup, and accessories compliment the dress? Was it a big moment in the actress’ career (increasing the longevity of the dress in the minds of viewers)?
1. Björk in Marjan Pejoski at the 2001 Academy Awards. This dress definitely has the wow factor but it doesn’t have much else. The reason this dress will go down in red carpet history is that it’s one of the most baffling dresses ever worn to the Academy Awards. Björk was so dedicated to this look that not only did she wear this boundary-pushing swan dress but she even dropped golden eggs on the red carpet.
2. Lupita Nyong’o in Prada at the 2014 Academy Awards. The actress stunned in this pale blue Prada gown with a plunging neckline, creating her very own Cinderella moment. Not only did she pick up a Best Supporting Actress Oscar for 12 Years A Slave but she also looked like she stepped right out of a fairytale. The consensus on this dress was clear when Nyong’o made it on almost every best-dressed list.
3. Sharon Stone in Vera Wang at the 1998 Academy Awards. Stone turned heads in 1998 with a lavender satin Vera Wang evening skirt and a white button-down shirt from the Gap. The best part? The Gap shirt had been taken right out of her then-husband Phil Bronstein’s closet!
4. Hilary Swank in Guy Laroche at the 2005 Academy Awards. This number is almost as memorable as Hilary Swank’s performance in Million Dollar Baby. Swank seemed to sense she would be taking home the Best Actress Oscar when she pulled out the perfect dress for the big night. The gown, comprised of 27 yards of navy blue silk jersey, was conservative in the front with long sleeves and a high neck but unforgettable from the back.
5. Penelope in Atelier Versace at the 2007 Academy Awards. Penelope Cruz attended the 2007 Oscars in one of the most memorable dresses of the decade. This dreamy Atelier Versace blush gown complimented the actress perfectly, and was unforgettable as she made her way down the red carpet with an extravagant feathered train. Although the actress lost to Helen Mirren for Best Actress, she made just about every best dressed list.
6. Gwyneth Paltrow in Tom Ford at the 2012 Academy Awards (left) / Gwyneth Paltrow in Ralph Lauren at the 1999 Academy Awards (right)
2012: Gwyneth Paltrow’s white Tom Ford dress and cape complete with Anna Hu Haute Joaillerie diamonds and a sleek ponytail oozed elegance. Her Tom Ford gown was a stark contrast to her fun look at the 1999 Oscars. This dreamy pink Ralph Lauren gown was unforgettable when Paltrow took the Best Actress Oscar for Shakespeare in Love.
7. Nicole Kidman in Balenciaga at the 2007 Academy Awards (left) / Nicole Kidman in John Galliano for Dior at the 1997 Academy Awards (right)
2007: Nicole Kidman stunned at the 2007 Oscars when she wore the breathtaking Balenciaga gown. The oversized bow made this dress stand out. When she wore the Dior gown, all eyes were on Kidman. She wore the risky color when everyone else was wearing primaries or pastels.
8. Michelle Williams in Vera Wang at the 2006 Academy Awards. When you look at this canary-yellow saffron Vera Wang, the color can be overwhelming. Fashion critics put it on both the best and worst dressed lists. Although it might not be for everyone’s taste, it got a reaction from everyone.
9. Julia Roberts in Valentino at the 2001 Academy Awards. Roberts chose a timeless vintage Valentino gown to take home her Best Actress Oscar for Erin Brockovich. Made for the couture collection in 1992, everyone fell in love with this vintage black gown with white detailing, giving the opportunity for more vintage dresses to make their way to the red carpet in the future.
10. Jennifer Lawrence in Dior Haute Couture at the 2013 Academy Awards (left) / Jennifer Lawerence in Calvin Klein at the 2011 Academy Awards (right). The face of Dior, Lawrence wore this voluminous ballerina pink ballgown to the 2013 Oscars that had everyone speechless. In 2011, Lawrence had already been nominated for Best Actress in Winter’s Bone. It was Lawrence’s first time attending the Oscars and the actress looked stunning in a slinky red Calvin Klein gown.
11. Halle Berry in Elie Saab at the 2002 Academy Awards. Halle Berry chose an unforgettable dress for an unforgettable night, not just in her career but in Oscars history. Berry was the first African-American woman to win an Oscar for Best Actress in Monster’s Ball. Aside from the momentous victory and Berry’s passionate speech, everyone was also in awe of this peek-a-boo Elie Saab floral gown, the perfect combination of feminine and sultry.
12. Cate Blanchett in Armani Privé at the 2016 Academy Awards (left) / Cate Blanchett in Givenchy Haute Couture at the 2011 Academy Awards (right). Blanchett was a sight to behold at the 2016 Oscars with this seafoam gown complete with 3D floral detailing. The dress also featured a gorgeous train, and her nude lip and light smokey eye complemented the look perfectly. Five years earlier Blanchett stepped out in this lilac Givenchy Couture gown with pearl details and hints of yellow. This avant-garde look won the hearts of critics everywhere and was one of the most fashion-forward looks of the evening.
13. Lady Gaga in Brandon Maxwell at the 2016 Academy Awards. Jumpsuits aren’t a common fashion choice on the Oscars red carpet, but Lady Gaga proved they could be as glamorous as any gown. The singer – always one to push boundaries – was a combination of fierce girl boss and Old Hollywood in this white Brandon Maxwell design showcasing pant legs in the front but giving the illusion of a dress from the back. Add simple, dangling earrings and a Marilyn Monroe-inspired hairstyle and this is a look to remember.
14. Reese Witherspoon in Tom Ford at the 2015 Academy Awards (left) / Reese Witherspoon in Vintage Christian Dior at the 2006 Academy Awards (right). The simple Tom Ford design was the perfect combination of elegant and bold for the Oscar-nominated actress representing her film Wild. On the other hand, the 1955 beaded, vintage Christian Dior gown was found by Witherspoon herself in a Paris boutique and it fit her so flawlessly it didn’t require a single alteration.
15. Angelina Jolie in Atelier Versace at the 2012 Academy Awards (left) / Angelina Jolie in Versace at the 2000 Academy Awards (right)
2012: The contrast between these Versace looks conveys the shift in Angelina Jolie’s image. Jolie is past her rebellious days of blood vials and regretful tattoos, but she couldn’t escape that thigh-high slit that had everyone focused on her leg. In 2000, Jolie’s Best Actress speech for Girl, Interrupted didn’t bring her the best publicity but it did prove her to be a talented actress. Jolie stuck to her gothic roots with an unforgettable long-sleeved black Versace gown and pitch-black hair extensions.
16. Octavia Spencer in Tadashi Shoji at the 2012 Academy Awards. Octavia Spencer sparkled at the 2012 Oscars when she chose a hand-beaded, ivory silk tulle Tadashi Shoji gown for her big night, taking home an Oscar for Best Supporting Actress for The Help. This beautifully detailed gown took 1,000 hours of work, a team of 10, and six fittings before it made its way to the red carpet. This embellished cinched dress was the epitome of a perfect fit.
17. Rooney Mara in Givenchy Haute Couture at the 2012 Academy Awards. Newcomer Rooney Mara had a strong debut at her first-ever Oscars, nominated for The Girl with the Dragon Tattoo. The up-and-coming actress channeled a modern Audrey Hepburn in this white gown that stood in stark contrast to her black hair and blunt bangs. The gown was complete with a daring neckline, dramatic train, and skin-toned satin bra closure in the back. Because the actress had shown a preference for black on previous carpets, this pearl-colored gown stunned fashion critics.
18. Charlize Theron in Dior Couture at the 2013 Academy Awards (left) / Charlize Theron in Gucci at the 2004 Academy Awards (right)
2013: It was Theron’s hair that made this look memorable; the pixie cut was edgy but complemented her white, peplum gown, and it was styled so perfectly it became more talked about than the dress. Her 2004 Gucci gown sparkling against Theron’s golden glow was beyond glamorous. Theron, who took home Best Actress for portraying serial killer Aileen Wuornos in Monster, stunned everyone in this gown because it was such a stark contrast to her character in the film.
19. Keira Knightley in Vera Wang at the 2006 Academy Awards. Keira Knightley stood out in this breathtaking burgundy Vera Wang gown before she was well-known, and it was this fashion moment that had everyone wondering who she was. The asymmetrical taffeta dress made it known that Knightley belonged on that red carpet. The best part? The actress donated the dress to charity the following morning!
20. Marion Cotillard in Jean Paul Gaultier at the 2008 Academy Awards. This dress of fish-like scales was a gorgeous choice for Marion Cotillard, who accepted the Best Actress Oscar that night for her role in La Vie En Rose. The Jean Paul Gaultier gown, covered in hundreds of mermaid-like scales and complete with a sweeping train, was a risky choice on Marion Cotillard’s part, but the stunning dress topped best-dressed lists in 2008.