Ranked: Memorable Oscar Dresses Of Year’s PastPublished on March 1, 2019. Updated January 29, 2020
There is no red carpet event that is more anticipated than the annual Academy Awards. Although the glamorous event is intended to honor Hollywood’s brightest accomplishments, some would argue that the red carpet fashion is an even larger part of the appeal. Stars such as Audrey Hepburn and Halle Berry have graced the Oscar’s red carpet in some of the most striking gowns that fans can still recall with clarity even decades later. Follow along for our roundup of the most memorable Academy Award dresses of all time from year’s past:
43. Lady Gaga — 2019
Lady Gaga looked absolutely striking on the 2019 Oscar red carpet wearing this sculptural black Alexander McQueen dress inspired by Breakfast at Tiffany’s. She even topped the look with a dazzling Tiffany & Co. necklace last worn by Hepburn when promoting her iconic film back in 1961.
42. Jennifer Lopez — 2019
Even though Jennifer Lopez wasn’t attending the Academy Awards on behalf of a nomination in 2019, that didn’t stop her from dressing to the nines. We absolutely loved this swoon-worthy mirrored dress worn by Lopez. It fit her like a glove, featured a stunning mirrored texture and showed off her figure without showing any skin. Absolutely flawless!
41. Michelle Yeoh — 2019
Crazy Rich Asians star Michelle Yeoh was undeniably one of the best-dressed women of the evening at the 2019 Oscars. She stepped out wearing a blush and silver Elie Saab number that featured the most beautiful foil embellishment. It was unique, whimsical and totally glamorous.
40. Regina King — 2019
Of all the looks at the 2019 Academy Awards, our favorite had to be this white pleated dress worn by Regina King. The look was classy and elegant, but still a little sultry with the thigh-high slit. Her look proved that sometimes simplicity is key when it comes to red carpet fashion.
39. Jessica Alba — 2008
Jessica Alba glowed at the 2008 Oscars where she stepped out showing off her budding baby bump in this deep purple Marchesa gown. The cut of this dress was highly flattering to show off her bump and we absolutely love the subtle feather detailing along the bodice.
38. Brie Larson — 2016
Brie Larson stunned at the 2016 Academy Awards where she stepped out wearing a cobalt blue dress with delicate ruffles trailing down the front. This deep jewel tone looked perfect with Larson’s skin tone and the beaded belt brought a touch of glitz to her red carpet ensemble.
37. Amanda Seyfried — 2013
Amanda Seyfried stunned on the 2013 Oscars red carpet where she stepped out in a halter dress designed by Alexander McQueen. The lavender and metallic number was the perfect choice to flatter Seyfried’s fair complexion and light features!
36. Cameron Diaz — 2010
Cameron Diaz looked like a total bombshell at the 2010 Academy Awards where she stepped out wearing this jewel-encrusted golden gown by Oscar De La Renta. The look fit her like a glove and was the epitome of red carpet glitz and glamour.
35. Anna Kendrick — 2010
Anna Kendrick looked absolutely gorgeous at the 2010 Academy Awards where she opted for a pale pink dress by Ellie Saab. The look featured subtle pleating in various directions and a sultry off-the-shoulder neckline. We especially love the floral embellishment on the bodice and the pop of lace on the slit.
34. Rachel Weisz — 2007
When Rachel Weisz stepped out at the Academy Awards in 2007 she instantly had all eyes on her. The starlet donned a slinky slip dress in a lovely shade of metallic silver. It was sultry, but totally red carpet glamorous, which is why it has stuck in our memory as one of the most memorable Oscars looks of all time.
33. Demi Moore — 2010
Demi Moore stepped out at the 2010 Oscars wearing a peach ruffled dress by Versace that no one could forget. The ultra fabulous look was detailed and intricated from the multi-tonal pleating on the bodice to the full ruffles on the skirt.
32. Natalie Portman — 2011
No one has mastered maternity style as well as Natalie Portman. The actress looked absolutely gorgeous at the 2011 Academy Awards where she stepped out wearing this off-the-shoulder violet number by Rodarte. The look flattered her budding baby bump and was the perfect rich jewel-tone to complement her golden complexion.
31. Angelina Jolie — 2012
Angelina Jolie’s leg slit took over the 2012 Oscars red carpet when she stepped out wearing this chic black look by Versace. The velvet dress was glamorous, sultry and an iconic Oscars fashion moment that no one could forget.
30. Naomi Watts — 2013
Naomi Watts stepped out at the 2013 Oscars wearing this gunmetal silver dress that fit her like a glove. We absolutely love the geometric cutout of this look around the neckline, which really made this stand out as a memorable Oscars fashion moment.
29. Cate Blanchett — 2016
Cate Blanchett looked absolutely angelic on the 2016 Oscars red carpet when she stepped out wearing this floral-embellished Armani Prive dress. We absolutely love the unique seafoam green shade of this dress and how much of a statement all the embellishment made.
28. Emma Stone — 2017
One of Emma Stone’s most memorable fashion moments is when she attended the 2017 Oscars wearing this Givenchy haute couture gown. The dress featured gold Swarovski crystal embroidery on the bodice as well as ombre crystal fringe along the skirt.
27. Alicia Vikander — 2013
Alicia Vikander absolutely stunned at the 2013 Oscars where she stepped out in this delicate lace gown in a flattering shade of teal blue. The beaded Ellie Saab gown showed off her dainty, petite frame perfectly but was still a little sultry with the mesh paneling.
26. Gwyneth Paltrow — 2012
Gwyneth Paltrow was a vision in white at the 2012 Oscars where she stepped out in this crisp and sophisticated dress by Tom Ford. The floor length cape was the epitome of Hollywood glamour and is definitely an Oscars look that we’ll never forget.
25. Anne Hathaway — 2009
Anne Hathaway stunned at the 2009 Oscars red carpet where she stepped out wearing this form-fitting metallic gown by Giorgio Armani Prive. The slinky number fit her like a glove and brought the red carpet glamour factor with its subtle shimmering texture. This look worn by Anne Hathaway is definitely a red carpet moment we’ll never forget!
24. Nicole Kidman — 2018
Nicole Kidman nailed her 2018 Oscars look when she stepped out wearing this royal blue number designed by Armani Prive. The look featured a plunging sweetheart neckline and an exaggerated bow detail along the hip. Kidman is definitely not shy to take a fashion risk or two, which we love about her, and this particular sophisticated look was undeniably a risk that was well rewarded!
23. Sandra Bullock — 2018
Sandra Bullock looked striking on the 2018 Oscar’s red carpet while wearing this shimmering Louis Vuitton gown! The custom-made black and silver garment featured a flattering halter-neckline and a ruffled detail cascading from the hip. The captivating number was the perfect balance of elegance and edginess.
22. Eiza Gonzalez — 2018
Eiza Gonzalez undeniably made head turns on the 2018 Oscars red carpet where she wore this show-stopping canary yellow number! The sun-kissed actress looked like an absolute bombshell and the sleek gown hugged her hourglass figure in all the right places. The look featured glamorous cutouts along the sides that showed an appropriate amount of skin without looking tacky. We love that she topped this look with an unconventional red lip for something different and for added drama.
21. Jennifer Garner — 2018
Jennifer Garner stole the show at the 2018 Oscars when she stepped out wearing this eye-catching Atelier Versace number. The brunette beauty rocked the striking cobalt blue number that featured an asymmetrical neckline and a dramatic cape which trailed elegantly behind her as she walked. This choice of color and cut couldn’t have been more perfect!
20. Grace Kelly — 1955
Grace Kelly is one of Hollywood’s most elegant icons, but her look from the 1955 Oscars was especially remarkable. The pale ice blue dress designed by Edith Head featured a dainty double strap and a luxurious silk texture that hugged her body perfectly. Suited for the classy woman she is, Kelly wore a pair of sleek white gloves as accessories and delicate pearl earrings. She coiffed her hair into an updo which was topped with romantic rosebuds throughout.
19. Audrey Hepburn — 1964
Audrey Hepburn was another Hollywood icon that looked absolutely striking whenever she stepped onto the red carpet! Hepburn’s floral look from the 1964 Academy Awards was definitely one of her most memorable. The Givenchy number was the epitome of old Hollywood glam with it’s A-line shape and couture detailing. The dress flattered her tiny figure and the belt-detailing around her waist further emphasized her petite frame.
18. Julia Roberts — 2001
Julia Roberts’ Valentino number from 2001 was one of her most breathtaking looks to date! The vintage gown featured a dainty halter neckline and a sleek, body-hugging shape that definitely stole the show. The vintage number was fitted and sophisticated but still romantic, especially with the glamorous train that cascaded behind her as she walked. The smooth updo definitely softened the entire look and added a touch of old Hollywood glamour.
17. Jennifer Lopez — 2003
Jennifer Lopez stepped out in 2003 wearing a mint green Valentino number that was the perfect color selection to flatter her bronzed complexion. The gown featured a stunning one shoulder neckline that had soft, sparkling embellishment around the edges. The look was definitely one of Lopez’s best of all time and although it was relatively clean and simple, it definitely made a lasting impression for years to come following the event.
16. Hilary Swank — 2005
Hilary Swank’s Guy Laroche navy number from the 2005 Oscars made one of the biggest fashion statements in red carpet history! At the time, a completely backless look like this was revolutionary, but it went on to inspire generations of designers for years to come. The stunning sapphire number proves that it doesn’t take embellishment or glitter to make a fashion statement and that often the cut of the dress is what makes the biggest impact.
15. Reese Witherspoon — 2006
Reese Witherspoon looked absolutely dreamy on the 2006 red carpet when she stepped out wearing a vintage 1955 Dior number. Rumor has it that Reese discovered the hidden gem tucked away in a Paris vintage boutique! She initially had trouble convincing the shop owner to part with it because, according to her, it had once belonged to royalty. Clearly, Reese won in the end and the result was an absolutely enchanting red carpet fashion moment.
14. Sandra Bullock — 2010
Sandra Bullock absolutely dazzled back in 2010 when she took to the Oscar’s red carpet wearing this glittering champagne number. The Marchesa garment featured a sheer bodice that had strategically placed embellishment and beading throughout. The gown flourished into a full glitter skirt that hugged her figure and trailed gracefully behind her as she walked. Bullock is hardly one to opt for sparkle on the red carpet which made this look all the more striking and notable.
13. Mila Kunis — 2011
Mila Kunis’ 2011 Academy Awards look definitely generated quite a bit of buzz! The eye-catching lavender number was designed by Ellie Saab and featured a chiffon texture, tiered lace detailing and a flattering ribbon which tied around the waist. We absolutely love the whimsical, romantic feel of this feminine gown and the soft purple color was striking against Mila’s dark features and hair.
12. Lupita Nyong’o — 2014
Lupita Nyong’o was a red carpet newbie when she stepped out at the Oscars back in 2014! She clearly knew how to make an impact and opted for a powder blue Prada gown that looked absolutely stunning on her. At the time, Nyong’o divulged that she picked the color specifically because it reminded her of her home, Nairobi. The pleated gown featured an elegant drop-style neckline and a full skirt which was completely glamorous, especially when topped with the sparkling diamond headband.
11. Taraji P. Henson — 2017
Taraji P. Henson turned heads when she stepped onto the 2017 Academy Awards red carpet wearing this luxurious velvet number. The Alberta Ferretti design featured an elegant off-the-shoulder neckline, which she topped with a chunky diamond necklace for added glamour. The cut of the dress was relatively simple, but the combination of the rich velvet with the thick diamonds was a display of Hollywood glitz at its finest.
10. Cher – 1988
Cher has always had a reputation for pushing the limits, but especially when it comes to fashion! In 1986, she attended the Academy Awards wearing a midriff-bearing two-piece outfit that would go down in history as one of the quirkiest red carpet looks ever. Two years later, she took the bold look up to another level when she attended the Oscars wearing a completely sheer dress that featured beading, embellishment, ruching and a sparkling scarf.
9. Gwyneth Paltrow – 1999
At the 1999 Academy Awards, Gwyneth Paltrow showed up wearing a pink taffeta Ralph Lauren gown, which featured V-shaped neckline and a long, wide skirt. Although some people criticized the dress because it wasn’t properly tailored, overall, it has been remembered as one of the greatest dresses ever worn on the Oscar’s red carpet and Paltrow was credited for bringing pink back in style.
8. Priyanka Chopra — 2017
No one could possibly forget Priyanka Chopra’s statement look from the 2017 Oscar red carpet! The crisp column-style dress was designed by Ralph & Russo and featured a geometric pattern throughout and a sharp square-shaped neckline. The look was a little avant-garde but still flattering and totally elegant. She topped the look with sparkling diamonds and sleeked her straight hair behind her ears.
7. Halle Berry – 2002
Halle Berry wore an Elie Saab dress to the 2002 Academy Awards that was definitely one of her most memorable looks ever. The top of the dress was made of mesh with some strategic embroidering over the chest with a maroon colored satin skirt. It’s considered one of the greatest Oscar dresses of all time because it was edgy and revealing, but at the same time left a lot to the imagination.
6. Michelle Williams – 2006
Michelle Williams didn’t win the Oscar for Best Supporting Actress in this saffron yellow Vera Wang gown, but she did receive critical acclaim for her bold fashion choice. While the color was initially panned, it became one of the hottest hues in Hollywood. The style of the dress combined with Williams’ bright red lips and wispy hair, she looked like she came out of an old Hollywood film.
5. Nicole Kidman – 2007
Nicole Kidman has attended so many Academy Award ceremonies over the years and she almost always lands on the best-dressed lists; however, there is one dress, in particular, that is by far the most memorable. In 2007, she wore a red eye-catching Balenciaga gown with a dramatic bow at the neck. Although she initially received a lot of flack for sporting a bow bigger than her head, all agreed that the dress was beautiful. It even sported a copycat at the 2012 Oscars with Emma Stone’s red Giambattista Valli gown.
4. Penelope Cruz – 2007
Penelope Cruz wore a stunning dusty pink feathered Versace number to the 2007 Academy Awards. The strapless gown flattered her hourglass figure flawlessly with its fitted bodice and long feathery train. Given the couture details on the dress, we’re not at all surprised that it is considered one of the most beautiful and iconic Oscar dresses of all time. She added a polished spin to the dramatic number by pulling her hair back into an elegant updo and showing off her chiseled collarbone.
3. Jessica Chastain – 2012
On the red carpet, Jessica Chastain’s fashion has been a hit or miss, but at the 2012 Oscars, she hit it out of the ballpark with this daring Alexander McQueen number. She looked absolutely regal in the black strapless gown, which featured a silk organza corset and gold beaded embroidery. This was definitely one of the more memorable of her gowns and it featured just the right amount of embellishment to be glamorous yet still tasteful.
2. Amy Adams – 2013
Amy Adams looked absolutely heavenly at the 2013 Academy Awards in this silver strapless Oscar de la Renta gown. The look featured a feathery tulle skirt and a flattering sweetheart bodice that ruched across the front. This dress was definitely memorable because it was sophisticated and sharp yet still made a statement. We love that Adams opted for a wispy updo with this look to truly allow the gown to steal the show.
1. Jennifer Lawrence – 2013
Jennifer Lawrence’s pale pink Christian Dior Couture gown that she wore to the 2013 Oscars was definitely the most dramatic dress choice at the event. With its strapless silhouette and ultra-voluminous skirt, she looked like she came straight from a Disney movie where she played the princess. It’s no wonder her outfit was so memorable – she was styled by none other than celebrity stylist Rachel Zoe!