The Most Disappointing Oscar Dresses Of All Time


The Academy Awards is one of the most anticipated awards shows in Hollywood. Not only is it exciting to see who takes home each award but it’s also fun to see all of the fashion hits and misses on the red carpet. Sometimes, even the most stylish stars can’t get it right on Oscar night. Follow along for our roundup of the top 18 most disappointing Oscar dresses ever. These ladies were chosen for this list because they usually exude so much style on the red carpet but, for whatever reason, they couldn’t pull it together and ended up disappointing fashionistas all over the world.

18. Jodie Foster — 1989

Jodie Foster definitely dressed to standout at the Academy Awards in 1989! Although we appreciate the risk, we’re not entirely sure the result was one of her better awards show looks. The sky blue dress definitely hugged her curves in all the right places, but the oversized frills draping from her hips seemed tacky rather than glamorous. It overwhelmed her frame and seemed to distract from her beauty rather than complement it.

Source: Everett Collection


17. Sophia Loren — 2009

Sophia Loren is a Hollywood legend, but unfortunately the dress she wore to the 2009 Oscar’s most definitely was not. The frothy golden number featured oversized ruffles and frill in all the wrong places in addition to strange sparkly straps and even more bizarre sheer mesh sleeves. To make matters worse, her makeup came across overdone and her pearl choker clashed with the texture of the gown.

Dee Cercone/Everett Collection

16. Hilary Swank — 2003

Hilary Swank has had a couple killer red carpet moments, but unfortunately, this frothy pink dress wasn’t one of them. The look was definitely elegant and whimsical, but many fashion critiques likened it as a dress that would be more suited for prom or a sweet 16 birthday party than the Academy Awards. We appreciate the dramatic effect of the sweeping skirt, but the tulle and ombre pink effect definitely came across a little too juvenile.

ABC/Courtesy Everett Collection

15. Jennifer Lopez — 2010

Jennifer Lopez is typically a red carpet all-star, which is why we were all the more disappointed when she stepped out in 2010 wearing this dramatic Armani Prive number. We’re used to J.Lo’s alluring and sleek red carpet gowns, and this ruffled, foofy number seemed to drown her hourglass figure. With a body as enviable as Jennifer Lopez, it’s a shame that she decided to wear a dress with such exaggerated layering and ruffles.

Source: Shutterstock

14. Diane Keaton — 2004

Diane Keaton has always had an out-of-the-box sense of fashion, but this particular look from the 2004 Oscar’s red carpet was definitely one of her most bizarre. The tuxedo look consisted of a long cutaway jacket which she paired with a striped vest, pants and polka dot tie. For accessories, Keaton opted for a top hat, leather gloves, and strange tinted glasses. We love a strong tuxedo look on the red carpet, but unfortunately, Keaton’s came across messy and distracting.

Source: Shutterstock

13. Tilda Swinton — 2008

Tilda Swinton is definitely one of the most influential style icons in Hollywood, but unfortunately, her 2003 look for the Academy Awards was not one of her best. The Lanvin dress featured a high-shine velvet texture that looked cheap rather than luxurious and sleek. The gown seemed to cling to all the wrong places of her body and the asymmetrical one shoulder long-sleeve seemed to drown her slender frame rather than flatter it.

David Longendyke/Everett Collection

12. Uma Thurman — 2004

Uma Thurman’s 2004 Oscar’s look was definitely one of the most questionable in red carpet history. The theatrical, costume-like look seemed to be something straight of a film rather than a respectable dress worn to an event that honors film. The look consisted of lace, a blue sash and heavy metallic detailing which did not pair well together. Thurman is such a natural beauty that we had high expectations for her red carpet appearance, but this look was an undeniable miss.

Source: Shutterstock

11. Celine Dion — 1999

Celine Dion’s 1999 Oscar’s look was definitely one of the most confusing of all time! Dion is known for her risky fashion looks, and often they are rewarded, but that was unfortunately not the case with this silk outfit. She broke fashion barriers by wearing her crisp tuxedo backward and pairing it with an oversized top hat. We love Celine’s tendency to step out of the box with her fashion, but this look was admittedly a little too bizarre to be praised.

Photo By Rex Features

10. Sarah Jessica Parker

Sarah Jessica Parker is known for her bold and beautiful red carpet looks. The actress wore a champagne-colored gown from the Chanel Couture Spring 2010 runway to the 82nd Annual Academy Awards and while the dress is unique, it does not flatter the Sexy and the City star’s petite figure and seems to drown her. With a figure like Parker’s, a more tailored dress that highlights the waist would be much more flattering.

9. Jennifer Garner

The plum coloring on this ruffled Gucci gown is flattering on Jennifer Garner and, if you aren’t considering the back of the dress, the front on its own is quite nice. The only problem is the mass of plumage-like ruffles cascading down the back. The back-detailing distracted from her natural beauty and enviable figure and we would have much preferred if she had opted for something a little more simple with less embellishment.

8. Anne Hathaway

Anne Hathaway opted to wear a pale pink Prada dress for the 85th Annual Academy Awards after she found out Amanda Seyfried was going to be wearing something remarkably similar to the Valentino gown she had originally selected. Unfortunately, the color and the fit of the dress were anything but flattering and the dress itself was quite underwhelming and dull. We understand the controversy and inconvenience of the last minute switch, but Hathaway definitely fell short of our fashion expectations with this look.

7. Halle Berry

Halle Berry wore a plunging metallic Versace gown to the 85th Annual Academy Awards and while some may argue that the dress looks sexy, we think it looks a bit too busy and doesn’t flatter her amazing curves. With her figure, something strapless with a mermaid cut would have been much more flattering. In the end, we just expected more from Halle and this dress ended up being a big disappointment.

6. Charlize Theron

Charlize Theron arrived at the 82nd Annual Academy Awards wearing the pink version of Lindsay Ellingson’s Dior Spring 2010 Couture gown. The details on the bust line are probably the most unflattering (not to mention, distracting) part of this dress. It draws way too much attention to the chest, which doesn’t translate to sexy on the Oscar’s red carpet.

5. Angelina Jolie

Angelina Jolie is one of the sexiest women in Hollywood; however, the black long-sleeved Versace gown that she wore to the 72nd Annual Academy Awards did nothing to show off her amazing body. The dress, combined with the heavy makeup and jet black hair, makes her look more like Morticia Addams than an Oscar-winning actress.We would have much preferred something a little more whimsical and light to celebrate her win rather than this dark, bland look.

4. Kate Hudson

Kate Hudson is the kind of actress who typically lights up the carpet with her California girl style and her youthful exuberance. Unfortunately, the Stella McCartney dress that she wore to the 73rd Annual Academy Awards, paired with a not-so-sophisticated frizzy up-do, seems to age the young actress by at least 30 years. The neckline was highly bizarre and seemed to distract from her enviable figure rather than flatter it.

3. Jessica Biel

Jessica Biel has one of the most beautiful faces in Hollywood with a perfect figure to boot, so her decision to wear this ill-fitted cream-colored Prada gown with oversized draping over the front makes absolutely no sense. In recent years Biel has proven herself to be one of the most well-dressed women to watch on the red carpet, but that’s not to say her past didn’t come with a few misses, like this dramatic number!

2. Gwyneth Paltrow

Style queen, Gwyneth Paltrow, wore this goth Alexander McQueen dress to the 74th Annual Academy Awards and, looking back on it, she sees some major issues with the dress! “There were a few issues; I still love the dress itself but I should have worn a bra and I should have just had simple beachy hair and less makeup. Then, it would have worked as I wanted it to – a little bit of punk at the Oscars,” she said.

1. Sandra Bullock

Sandra Bullock can be hit-or-miss on the red carpet but when she wore this black and white Marchesa dress to the 84th Annual Academy Awards, it was admittedly a great disappointment. The actress has an amazing figure and with the lack of tailoring, you can’t see her amazing curves at all. The top looks too big and the bottom looks like it belongs to another dress altogether. Bullock has had a handful of awe-worthy red carpet moments, but unfortunately, this look was definitely not one of them.