Editors handpick every product that we feature. We may earn money from the links on this page.

The Worst Oscar Dresses of All Time

Here's hoping 2020 keeps things fresh.

image
Getty Images

We're finally reaching the end of awards season, and it's all led up to the most important gong in showbiz: The Oscars. On Sunday, actors and actresses will travel to Hollywood from all around the world for a little recognition from The Academy. Last year, we got a steamy performance from Lady Gaga and Bradley Cooper, an insane amount of sexy dresses, and, of course, the drama that led to the awards having no host for the first time since 1989. There was plenty to love, but there were also a few unforgettable looks on the red carpet, and I don't mean that in a good way. I get it, picking a gown for Hollywood's biggest night can be hit or miss, but these gowns from past years' Oscars were definite misses. (They also made me really love my three-year-old-sweatpants I watched the Oscars in.)

image
Getty Images
Lady Gaga

The highlight of the 2015 red carpet was definitely Lady Gaga's red gloves, which spawned plenty of memes. My favorite? The Lady Gaga "cleaning starter pack."

1 of 26
image
Getty Images
St. Vincent

St. Vincent took a risk at the 2018 Academy Awards in this Saint Laurent look. It's hard to hate anything from the iconic fashion house, but this runway ensemble didn't work IRL.

2 of 26
image
Getty Images
Bjork

Icelandic artist Bjork's swan dress is probably the most iconic on the list of worst dressed. The look was designed by Macedonian designer Marjan Pejoski, who actually made two copies of it as it could not be dry cleaned. One was auctioned off for $9,500 in 2005 (!!) and Valentino even paid tribute to this swan ensemble in its spring 2014 couture fashion show.

3 of 26
image
Getty Images
Faith Hill

The singer's dress for the 74th Academy Awards resembled a rainbow cake explosion. We're not sure what made Hill decide on this look, but it's a hard pass from us.

4 of 26
image
Getty Images
Uma Thurman

The actress looked like she was drowning in her dress at the 76th Annual Academy Awards. And, question: Are the gold and blue embroidered pieces remnants of a vest? We're confused.

5 of 26
image
Getty Images
Whoopi Goldberg

I saw this dress and immediately thought "Count Dracula." Sorry, Whoopi.

6 of 26
image
Getty Images
Kate Hudson

The actress looked unrecognizable (and not in a good way) at the 2001 event, when she stepped out in this gray dress with a fringe neck shawl. I prefer to remember her in this 2014 Atelier Versace look instead.

7 of 26
The 74th Annual Academy Awards - Arrivals
Steve Granitz
Sally Kirkland

There's a laundry list of things of things that aren't great about this dress. But the rhinestone bindi was an extra layer of WOW.

8 of 26
image
Getty Images
Sophia Loren

The iconic star was the "Belle" of the ball in this yellow ruffled number at the 2009 Academy Awards.

9 of 26
image
Getty Images
Lizzy Gardiner

Costume designer Lizzy Gardiner wore a dress made out of gold American Express cards to the 1995 Academy Awards. The cards were real, but had expired. That year, she won an Oscar for Best Costume Design for The Adventures of Priscilla, Queen of the Desert, but in an ironic twist of fate, this dress landed her on worst dressed lists.

10 of 26
image
Getty Images
Kelly Ripa

The star wore a strapless Christian Siriano creation to the 2018 Academy Awards. From the front, the gown looked great. From the back? That's another story.

11 of 26
image
Getty Images
Edy Williams

The year is 1974. The outfit is a leopard printed bikini underneath a spotted furry coat. Perhaps she had a backup gown...in the car?

12 of 26
image
Getty Images
Susan Sarandon

The actress arrived to the 1996 Oscars in a Dolce & Gabbana gold gown. She matched the Academy Award statue.

13 of 26
image
Getty Images
Sally Kirkland

The actress looked like she was ready to fly away in this semi-sheer multi-colored dress at the 2007 Academy Awards.

14 of 26
image
Getty Images
Demi Moore

At least Moore can say she was an early adopter of biker shorts.

15 of 26
image
Getty Images
Geena Davis

The actress looked like a runway Las Vegas bride at the 1992 Academy Awards.

16 of 26
image
Getty Images
Kim Basinger

The star arrived to the 1990 Academy Awards in a white gown with one shoulder ripped off and a corseted bodice. The look did not seem comfortable at all.

17 of 26
image
Getty Images
Hilary Swank

The actress and Tyra Banks (see next slide) should have gone to the Oscars together, as Swank's Dior dress was more suited for prom than the Academy Awards.

18 of 26
image
Getty Images
Tyra Banks

The model's giving me sugar plum fairy vibes with this poufy purple gown dress from the 2000 Academy Awards.

19 of 26
image
Getty Images
Helena Bonham Carter

Bellatrix Lestrange is that you? Carter appeared to channel her Harry Potter character's preference for moody colors with this black-and-white multi-layered dress at the 2013 Academy Awards.

20 of 26
image
Getty Images
Cher

Two questions: how is that skirt staying on and is that headpiece heavy? Cher wore this dominatrix-meets-fortune teller outfit to the 1986 Academy Awards and it was just as memorable as you'd expect.

21 of 26
Arrivals At 67th Academy Awards
Barry King
Lizzy Gardiner

It was 1995 and apparently plastic was really in for this costume designer. I guess this is one way to keep yourself from swiping your American Express card...

22 of 26
The 74th Annual Academy Awards - Arrivals
Steve GranitzGetty Images
Heather Mills

Heather Mills arrived in lacy separates for the 74th Annual Academy Awards in 2002. In hindsight. this outfit wasn't the best choice for a fancy red carpet event—especially the Oscars, where glamorous gowns or sleek pantsuits are de rigueur.

23 of 26
image
Getty Images
Melissa McCarthy

The comedian wore a gray David Meister dress to the 2013 Academy Awards. Though the dress had some embellishments on the shoulder and sleeves, plus ruching in the middle, it looked washed-out. We'd love to see her in a brighter look.

24 of 26
image
Getty Images
Jennifer Hudson

The actress and singer arrived at the 2007 Academy Awards in a brown Oscar de la Renta look. Though the dress itself was fine, her cropped outerwear reminded us of something The Tin Man would wear.

25 of 26
The 74th Annual Academy Awards - Arrivals
KMazur
Jennifer Connelly

It's such a shame this Balenciaga number washed Jennifer out. because she took home a Best Supporting Actress Oscar for her role in A Beautiful Mind that night. Unfortunately, the dress was ill-fitting and the scarf was incredibly unnecessary.

26 of 26
Advertisement - Continue Reading Below
More From Fashion