Top 10 Worst Oscar Outfits of All Time
Trivia Top 10 Worst Oscar Outfits of All Time



Top 10 Worst Oscar Outfits of All Time

Top 10 Worst Oscar Outfits of All Time

Script written by Nick Spake

When you think of the Oscars you think of glamour, glitz and beautiful outfits. But sometimes you get some celebrities who clearly thought they were going elsewhere. Perhaps they were trying to make a fashion statement, but boy did they miss the mark. In this countdown we take a look at the Top 10 Worst Oscar Outfits of all Time! We've included Bjork's famous dead swan dress, Whoopi Goldberg's hideous green and purple outfit, Cher's black showgirl Bob Mackie ensemble, Celion Dion's backwards suit, Faith Hill's rainbow disaster gown and Tilda Swinton's curtain dress.

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Top 10 Worst Oscar Outfits of All Time

Somebody alert the Fashion Police ASAP! Welcome to MsMojo and today we’ll be counting down our picks for the Top 10 Worst Oscar Outfits of All Time.
For this list, we’re taking a look at the ugliest getups that celebrities have worn to the Academy Awards.

#10: Faith Hill
“74th Academy Awards” (2002)

At the 72nd Academy Awards, Faith Hill performed a heartfelt rendition of “Over the Rainbow” from “The Wizard of Oz.” When the country music star returned to the Oscars a couple years later, she literally wore all the colors of the rainbow. This fashion choice ultimately backfired on Hill, however, as her ensemble resembled a handful of Skittles melted into a pack of Starburst. Fortunately, she did a costume change later that night, wearing an elegant black dress during her performance of "There You'll Be" from “Pearl Harbor.” It proved to be wise decision, as a bright, colorful dress really wouldn’t go hand in hand with a movie about an American tragedy, but this also begs the question of why she didn't just wear black in the first place.

#9: Hilary Swank
“75th Academy Awards” (2003)

With two Oscars on her mantel, there’s no denying that Hilary Swank is one of the most accomplished actresses in the business. She didn’t exactly dress for success at the 75th Academy Awards, though. Attending the ceremony to present one of the Best Picture nominees, Swank dawned a pink Christian Dior gown. This mini dress came complete with a laughable pink tulle overlay, calling a ballerina to mind. This dress probably would’ve been acceptable if Swank was going to a high school homecoming dance, but this was no homecoming dance! By comparison, her characters in “Boys Don’t Cry” and “Million Dollar Baby” suddenly looked a lot more glamorous.

#8: Celine Dion
“71st Academy Awards” (1999)

There are plenty of classy women that can pull off the tuxedo look. Sadly, this wasn’t the case for Celine Dion at the 1999 Oscars. Why? For starters, she put the jacket on backwards! Was this supposed to be some sort of fashion statement, or did Dion forget to look in the mirror before leaving her house? It didn’t help that the French Canadian singer also wore an outlandish hat and $25,000 diamond-studded Ray-Ban sunglasses. To her credit, Dion reportedly wore these ridiculous sunglasses because Ray-Ban offered to donate $50,000 to her charity for cystic fibrosis. In an interview with Entertainment Weekly, though, Dion’s stylist stated, “I wish I could have given $50,000 for her not to wear those glasses.”

#7: Gwyneth Paltrow
“74th Academy Awards” (2002)

In order amp up the sex appeal, it isn’t uncommon for actresses to go braless on the Red Carpet. A brassiere would have saved Gwyneth Paltrow from an all-out fashion disaster in 2002, however. Although her Alexander McQueen dress was drab, uninspired, and even kind of gothic, she might’ve been able to fly under the radar if it weren’t for her see-through top. This made it all the more apparent that Paltrow wasn’t wearing a bra, revealing more than she intended. Years later in a GOOP interview, the Oscar-winner admitted that forgoing a bra was a huge mistake.

#6: Geena Davis
“64th Academy Awards” (1992)

What is this, a rejected costume from “Moulin Rouge?” Nominated for her performance in “Thelma & Louise,” Geena Davis sported this low-cut bustier dress at the 64th Academy Awards. Featuring a ruffled train and donning black tights, Davis looked like a can-can dancer getting ready to walk down the aisle. It isn't beyond the realm of reason to think that her dress wasn’t finished. Maybe the designer ran out of time, threw something together at the last minute, and Davis just had to roll with it. In any case, it’s a dress that epitomizes ‘90s fashion at its absolute worst... although at least it wasn't neon....

#5: Tilda Swinton
“80th Academy Awards” (2008)

Upon winning an Academy Award for her supporting performance in “Michael Clayton,” Tilda Swinton became a Hollywood A-lister. It’s just too bad she didn’t wear a better outfit to commemorate such a special occasion. Her one-sleeved dress would’ve been more appropriate for a toga party than an Oscar party. Looking like a bunch of trash bags sewn together, it's as if Swinton raided the “to donate” section of the Paper Bag Princess’ wardrobe. Although some critics applauded Swinton for her unconventional fashion choice, this black velvet gown was also widely considered one of Oscar’s biggest fashion fails ever. Just because a dress is unique doesn’t automatically make it stylish.

#4: Kim Basinger
“62nd Academy Awards” (1990)

After appearing in Tim Burton’s “Batman,” Kim Basinger became one of the most desired actresses on the planet. The blonde bombshell turned plenty of heads at the 1990 Oscars, although people were primarily drawn to her bizarre dress. Actually, we’re not even sure if this eyesore can be classified as a dress. It’s as if the designer started off making a white jacket, but then decided to modify it into a gown halfway through. The result is a horribly misguided mash-up, complete with one sleeve, one glove, and one massive skirt. Basinger might’ve played Bruce Wayne’s girlfriend, but this goofy getup is more Two-Face than it is Vicki Vale.

#3: Cher
“58th Academy Awards” (1986)

Cher has never been one to shy away from bold fashion statements, especially when it comes to award shows. At the 1986 Oscars, the singer/actress showed off her belly button in a jaw-dropping ensemble. Giving her the appearance of a showgirl, this Bob Mackie ensemble came complete with a flashy loincloth and a feathered headress. She even joked about her fashion choice while presenting the Best Supporting Actor Oscar, noting that this isn’t how serious actresses are expected to dress. Cher would wear an equally strange outfit to the 60th Academy Awards, although this time she walked away with Oscar gold.

#2: Whoopi Goldberg
“65th Academy Awards” (1993)

Whoopi Goldberg not only has an Oscar to her name, but an Emmy, BAFTA, Grammy, and Tony as well. While she’s bound to go down as one of the most versatile entertainers who ever lived, Goldberg definitely won’t be remembered as a fashion icon. Case in point, her inexplicable outfit at the 1993 Oscars. The purple exterior was already tacky enough, but it’s the lime green lining that really burns the eyes. These two colors simply don’t work well together and those repugnant pants didn’t do Whoopi any favors either. The whole ensemble makes her look like a peacock.
Before we get to our top pick, here are a few honorable, or in this case dishonorable, mentions:

Charlize Theron
“82nd Academy Awards” (2010)

Uma Thurman
“76th Academy Awards” (2004)

Demi Moore
“61st Academy Awards” (1989)

#1: Björk
“73rd Academy Awards” (2001)

This outfit not only stands out as one of the most notorious moments in Oscar history, but also in pop culture in general. The Icelandic artist shocked everyone when she stormed onto the red carpet in this ensemble. With a swan head wrapped around her neck, it looked as if Björk was wearing road kill- regal road kill, but road kill nonetheless. Was Cruella De Vil her designer or something? Unsurprisingly, the swan dress has been parodied in movies and TV shows. But with all that said, the dress left a huge impression and was even showcased at the MoMA museum. So perhaps it's an ugly duckling of a swan that blossomed into a beautiful swan of a swan... or maybe not.

Do you agree with our list? What do you think is worst Oscar outfit ever? For more entertaining Top 10s published every day, be sure to subscribe to MsMojo.