The Unexpected Oscar Dresses Of Year’s PastPublished on March 1, 2019. Updated January 29, 2020
The Academy Awards is one of the most anticipated events in Hollywood each awards show season. Not only is it exciting to see who takes home each award but it’s also interesting 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 Oscars night. Follow along for our roundup of the unexpected Oscar’s dresses of year’s past.
35. Emily Blunt — 2018
Emily Blunt undeniably missed the mark with this powder blue number on the 2018 Oscars red carpet. The chiffon dress featured an outdated looking high-neckline and cap sleeve detailing. This look seemed to age Blunt and was a little too matronly, especially with the doily-looking lace embellishment.
34. Gemma Chan — 2019
Crazy Rich Asians star Gemma Chan has proved she has a strong sense of style based on her previous red carpet looks in 2019, which is why we were disappointed with this unshapely pink number she opted for at the Oscars. The color looked fabulous on the skin tone, but this dress simply did nothing for her figure and felt like it drowned her.
33. Kacey Musgraves — 2019
We were totally shocked by this baby pink look worn by Kacey Musgraves at the 2019 Oscars. It was the definition of foofy and many fans tuning in even compared her look to a loofah! As much as we love and support Kacey Musgraves, this dress simply wasn’t the most flattering.
32. Charlize Theron — 2019
We have high expectations for Charlize Theron when she hits the red carpet, but we, unfortunately, weren’t thrilled with her choice of dress for the 2019 Oscars. The look didn’t feel properly tailored to her body, especially with the cuffed sleeves, and it wasn’t the most flattering option for her statuesque figure.
31. Emma Stone — 2019
Of all the red carpet looks at the 2019 Oscars, we were most disappointed with this strange look worn by Emma Stone. The look was designed by Louis Vuitton and featured a bizarre checkered chocolate and gold print. Many were comparing her look to a waffle, which we can totally see!
30. Anne Hathaway — 2007
No one could forget the dress Anne Hathaway wore to the 2007 Oscars! The shape and style of the dress itself aren’t too bad, but the oversized bow detail along the chest definitely received a lot of backlash from fashion critics. Her look would have been much sleeker and stylish without this distracting detail.
29. Emma Stone — 2018
Of all the looks from the 2018 Oscars, we were by far the most let down by Emma Stone’s outfit. Stone made a huge impression at the 2017 Oscar red carpet with her gold column-style dress, which is why we had big expectations for her look the following year. The red and pink blazer combo she opted for seemed quite casual and the colors clashed, which was disappointing. There was also too much silk happening at once and we wish she would have mixed up the textures.
28. Jennifer Hudson — 2007
Jennifer Hudson stepped out at the 2007 Oscar awards wearing a chocolate brown dress with pockets that landed at the top of nearly every worst-dressed list. To make matters worse, she topped the look with a strange sculpted bolero jacket which clashed and felt over the top.
27. Lady Gaga — 2015
Lady Gaga has made a name for herself over the years for her bold and eccentric sense of style, but her look for the 2015 Oscars just left us totally confused. The dress itself wasn’t too bad and was actually quite pretty with the sculpted shoulders and glittering texture, but the red, rubber glove-like accessory she wore on her hands totally detracted from the dress.
26. Jennifer Connelly — 2002
We have to admit we weren’t the biggest fans of the taupe layered dress that Jennifer Connelly wore to the 2002 Academy Awards. The look felt shabby, especially with the raggedy tiers trailing down the skirt. To make matters worse, Connelly topped her look with an extra long yellow scarf which, unfortunately, detracted from the look even further.
25. Faith Hill — 2002
Faith Hill attended the 2002 Oscars wearing a rainbow dress that will forever be remembered as one of the most disappointing Oscars looks. From the heavy beading to the pastel range of colors, this look definitely felt overwhelming, and ultimately, over the top.
24. Bjork — 2001
How could we forget Bjork’s infamous swan dress from the 2001 Oscars? The Icelandic singer donned a feathered frock by Marjan Pejoski with no shame and this eccentric creation has undeniably landed her on many worst dressed lists over the years. We’ve seen tasteful feathers on dresses throughout red carpet history, but never before had we seen a full blown bird worn as a gown.
23. Juliette Binoche — 1997
Juliette Binoche stepped out at the 1997 Oscar awards wearing a head-to-toe velvet dress that no one could forget. Unfortunately, the dress felt quite heavy with the dark velvet texture and was a little too vampire-esque for our taste.
22. Charlize Theron — 2006
Charlize Theron stepped out at the 2006 Oscars wearing a dress designed by Galliano for Dior. Her look was, unfortunately, a little too bold for our liking, especially with the oversized bow detail on the shoulder that was totally distracting.
21. Kate Winslet — 2016
Kate Winslet stepped out at the 2016 Oscar awards wearing a Ralph Lauren dress that had one major issue — the texture! The dress picked up on camera looking almost latex-like with the glossy finish, which really came across quite tacky and strange.
20. Dakota Johnson — 2017
Dakota Johnson’s 2017 Oscars dress definitely earned a lot of buzz following the event, but unfortunately not in a positive way. The star hid her fabulous figure among layers of silk and the entire dress seemed outdated and almost as if it belonged in the Victorian era with its ruffled collar, puffy shoulders, and long sleeves. The Gucci gown was overly modest, a strange yellowed shade of champagne and featured a bizarre ruffle detail at her waist that was super unflattering.
19. Salma Hayek — 2018
Of all the looks from the 2018 Oscars, we were the most confused by Salma Hayek’s sequin gown, The obscure look felt quite tacky and juvenile which was disappointing to see on the ever-elegant Hayek. There was purple, glitter, diamonds, and tiers which simply came together to look quite chaotic and questionable.
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.
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.
16. Hilary Swank — 2003
Hilary Swank has had a couple of 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.
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.
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.
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.
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.
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.
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.