25 Most Controversial Oscar Dresses In History

The annual parade of stars on the Red Carpet before the Academy Awards has become as popular as the Awards themselves. Who’s wearing which designer is as important as who wins Best Actress. Is it shallow and sexist? The men on the red carpet are rarely asked which fashion mogul designed his suit. The men are asked about their work, the women are asked about their dresses; a fact which led to the trending hashtag #askhermore at the 2015 Oscars.

But the obsession with actresses’ dresses is not necessarily a case of sexism so much as the appeal of the glamor that starlets have always epitomized. There are more aesthetic enjoyments and diversity to be had in dresses than in tuxedos. The sight of talented, impossibly beautiful women impeccably made up is an escapist fantasy, and there’s a much larger palette for women to work with creatively.

This year, the red carpet was relatively tame; although many high profile stars chose to disrobe for the after parties, pictures in scandalously revealing outfits – like Rita Ora, pictured above.

The most remembered dresses in Oscar history, however, are the worst. It seems the wealthy and glamorous can be just as susceptible to bad taste as the rest of us mere mortals. TheRichest has conducted a survey of fashion brain cramps from sources ranging from Cosmo to Time Magazine. A lot of offenders are so memorably and gobsmackingly ugly, they’re regularly cited as the worst Oscar dress picks of all time. And as for the absolute worst Oscar robe of all time, there is absolute unanimity.

25. Jennifer Connelly, 2002

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Sure anything goes with an Oscar and she won the best-supporting-actress award for “A Beautiful Mind” that night. She might also have been nominated for her role in “A Hideous Dress.” Or would have been if there were an award for it.

Designed by the Balenciaga, more known for bold fabrics and color, it brings to mind what happens when you put the white drapes in with the dark color laundry load. The long chiffon scarf is maybe supposed to be offsetting, but the whole not-matching-for-no-apparent-reason thing is more off-putting.

The BBC described the color as “pale dung.” That’s pretty vicious for the Brits. Joan Rivers worked for the BBC?

24. Faith Hill, 2002.

Back to back fashion faux pas for the 2002 red carpet. Where Connelly’s fashion faux pas was the essence of drab, the country and western superstar’s colorful Versace gown looks like it was inspired by a tequila sunrise. Or perhaps several.

Faith Hill was there to perform the Oscar-nominated song There You’ll Be, which won for Best Song. There might have been some crossed wires because it seemed like she dressed to perform Somewhere Over the Rainbow.

23. Kim Basinger 1990

Blessed as she is, Basinger looks amazing in anything. But this fashion confection that she proudly designed herself had the catty claws out. Yes it does look like it would have got a C-minus at a community college fashion course. Among its many noted sins, one critic noted that Kim Basinger’s dress at the 1990 Oscars made her look more like a drunk Disney princess than a well-respected actress.

On another outfit, the half-missing jacket might have been ‘asymmetrical’ but with all that other poof it just looks bizarre,

That was the year she won a Science Fiction Festival Best Actress Award for her role in “My Stepmother is An Alien.” Perhaps this was the costume for the sequel, “My Dressmaker is an Alien, too”.

22. Diane Keaton, 2004.

The year Diane Keaton was nominated for best actress in “Something’s Gotta Give”, something did give. Her fashion reputation.

She seems to be channeling her inner Charlie Chaplin with her Little Tramp outfit. It seems like the charmingly goofy mismatched look that became an actual fashion trend after she won Best Actress for ‘Annie Hall’.  But after 26 years, the look can be officially declared, at the very least, ‘last week’.

Still, those are great shoes and there is no statute of limitations on great shoes.

21. Tilda Swinton 2008

This infamous dress was washed black silk designed by Lanvin to set off Tilda Swinton‘s red hair and delicate complexion. So often was it described as a bunch of “black velvet garbage bags holding her body hostage”, there was speculation the true designer was the Man from Glad.

If minimalism was the object, this dress missed. The effect is gaunt at best, like three-quarters of a body bag. A fifteen grand bodybag. People still search for the meaning of the single sleeve.

How sad that every time she revisits her big night winning the Best Supporting Actress Oscar, Tilda sees this and thinks “What was I thinking?” It was said that she liked it so much she kept the dress instead of the usual donation to charity.

 20. Tyra Banks, 2000

The first thought on seeing this dress is that a little lavender goes a long way. The volcanic supermodel got a Lifetime Achievement Award for this – not from the Academy for acting, but from the media, who will rip her every year at Oscar time.

Reviewers had loads of fun with this one. A Barbie robot. Bad prom dress, toilet-roll holder, and The Human Swiffer.

Facebook page Oscar Fashion Hall of Fame and Shame praised her environmental ethics for recycling one of her old bridesmaid’s dresses and thanked her for leaving the matching hat and parasol at home.

19. Marion  Cotillard 2009

Being photographed next to Penelope Cruz is a brave thing to do, but the lovely European holds her own. The year before she had looked classically stunning in a Gaultier form-fitting white gown as she accepted her Best Actress award for her tremendous performance as Edith Piaf in La Vie en Rose.

However, this Dior haute couture number in 2009 looks overwrought and excessively billowing. Except for the blue trim, it looks like something Scarlett O’Hara would have worn to a funeral in the Old South. If you look at the striped fabric insert long enough it looks like she’s wearing a megaphone in her left leg.

 18. Charlize Theron, 2010

First let it be said, Theron is one of those who appears in both Halls of Fame and Shame. She looked to die for in her Vera Wang dress in 2000. But the Fashion Police really had a hate on for this 2010 look.  Those bodice swirls struck many as tacky, like a cheap burlesque costume.

And honestly, as 0ne of the most beautiful women ever to walk the face of the earth all she needs is a plain black gown and a little mascara. Who sold her on this hybrid Dior Haute Couture with a breastplate from a Nordic Goddess of War?

Despite the thumbs down from critics, she said, “I just loved this dress.”

17. Jodie Foster, 1989

The British fashion magazine Marie Claire hated this dress so much they pronounced “redemption will not be possible.”

The legend is that Foster saw the dress in a shop window in Rome. Not a bad thing. But the mistake, according to one reviewer, was that Foster “did not then give the dress to a younger cousin for her senior prom but kept it for when she won her first Oscar, for The Accused”.

Gifted directors like Foster agonize over every frame, every edit checked for composition and continuity. So it’s hard to picture her checking one last time in the mirror that evening before leaving the house, seeing light blue fins coming out her butt and saying “ Yup, Good to go.”

16. Susan Sarandon, 1996

This was a triumphant evening for Sarandon, winning an Oscar for her performance in Dead Man Walking. Her choice of gown got far worse reviews .

One reviewer guessed the hair and dress color came out of the same bottle of Chocolate Macaroon L’Oreal Color Expert.

Sarandon is a wonderful actress, a good person with a social conscience, forever to be remembered fondly as Annie in Bull Durham and Louise in Thelma and Louise. But everyone makes mistakes.

15. Gwyneth Paltrow, 2002

This is like a team effort, an experiment to make one of the most photogenic people in film seem sad and frumpy.

The see-through vest gives Paltrow a droopy looking bust, the skirt made her look shapeless and the excessive eye makeup looks teen-goth inspired.

One reviewer said “I  like it because it’s a small token of proof that Alexander McQueen, possibly the greatest fashion designer of all time, was also a fallible human being.” Gwyneth insisted she loved this outfit and told Harper’s Bazaar the problem was the braided hair.

14. Miley Cyrus, 2009

Miley may have scandalised many fans with this fashion faux pas, but that was before anyone could have anticipated the horror that would be Miley’s fashion sense five years’ hence.

The gown was too old for her, the endless scallops cascade over her and the carpet, and the whole thing makes her look like Hannah Montana trying too hard to impersonate a grownup. She ends up looking more like the frump girl from the ‘burbs at the Grad Dance.

The Guardian was even cattier describing it as “a rhinestone encrusted gown made out of granny’s doilies.”

13. Uma Thurman, 2004

We could give Uma the benefit of the doubt, speculating that she was coming straight from the wrap party of a remake of The Sound of Music. This alpine-inspired Christian Lacroix sure got a few yodels in the carpet.

Her father is a philosopher and maybe that was why she sounded philosophical about spending tens of thousands of dollars on a dress no one liked. “Everyone looked the same. Everyone had it down to such a perfect T…You get bored. That’s when you have to say, ‘I will be worst-dressed.”

You have to admire her for setting a goal and achieving it totally.

12. Kate Hudson, 2001

Poor Kate Hudson. This was her big night, nominated for Best Supporting Actress for her wonderful work as a rock and roll groupie in Almost Famous.

But she and designer Stella McCartney were eviscerated for this frock. Critics started with the tassels and went on to the cape (which McCartney apologized for), then the Victorian box purse and finally the hair which was taken aside for its own crucifixion. It does bring to mind Joanie Cunningham in ‘Happy Days’.

In a 2012 interview with New York magazine, Kate said she had totally forgiven McCartney and that “I felt so beautiful, and I have it in my closet still to the day.” In return, friend McCartney said, “I blame the hair.”

11. Charlize Theron, 2006

Theron is a repeat offender. Avant garde can be OK, especially when you have Ms. Theron’s assets. But this is more like a bunch of fabric strips were stitched together by a bunch of elves on drugs. Except for the one who did that big bow – that elf was definitely drunk.

The Fashion Police website said “You either loved it or hated it. We hated it. The bow on her shoulder looked like it weighed more than she did”.

10. Georgina Chapman, 2010

This dress brings to mind an old Western movie, what the hooker with a heart of gold might wear to the hoedown. The excessive shoulder straps and bling apparently hail from the Swiss Army Knife collection. Georgie Chapman is a fashion designer herself, so this must be a self-inflicted wound and on those grounds alone she earns her Top Ten status.

9. Lizzy Gardiner, 1995.

This dress is truly, memorably awful. The Oscar-winning costume designer strung together 254 American Express Gold cards and actually wore them in public. It suggests an amended form of the old Amex ad slogan: “Don’t Leave Home With It.”

A point in Lizzy’s favour: the dress raised more than $12,000 for AIDS research. But can you imagine being a director or producer meeting her in that get-up and thinking “I will stick hot needles in my eyes before I let that woman anywhere near my next film.”

She won her Oscar for Priscilla Queen of the Desert. Now it kind of makes sense.

8. Celine Dion, 1999.

This is not so much an outfit as it is a clear cry for help.

The Canadian singer, like most women, could have looked quite fetching in a John Galliano white tuxedo. But wearing it backwards and adding a hat was not a great choice. Jessica Winter opined that “The pants were mis-delivered from a Big and Tall Men’s Shop catering to hospital staff.”

Best summed up by another scathing review, “She looked like she was going the wrong way to an all-white funeral procession.”

7. Whoopi Goldberg, 1993

She’s a comedian, so one might hope she was just kidding. Was it a tongue-in-cheek reference to her fabulous performance in The Color Purple? Was it an impersonation of what a Teletubby might wear if nominated?

One reviewer guessed maybe Whoopi was trying to dress like Kim Basinger’s African American fairy godmother. The saddest thought is that such a popular woman didn’t have a single friend to stage an intervention.

6. Hilary Swank, 2003

This was an unflattering dress for the remarkably beautiful Swank. But there was not much of an effort in the hair and makeup departments. As for the dress, the fashion director of Marie Claire magazine eagerly named Ms. Swank the worst-dressed woman at the 2003 Oscars.

The Guardian concurred. “Last night’s pink, gauzy mess looked simultaneously cavity-inducingly sweet and depressingly frumpy.It’s a safe bet that Vogue won’t be using her as a cover girl again anytime soon.”  Really, she had a better wardrobe as the boxer in Million Dollar Baby.

The unfortunate dress hasn’t put much of a crimp in her career though. Perhaps having the talent to win two Oscars is a more important measure of a person.

5. Demi Moore, 1989

Ms. Moore must have pedaled over to the theater since she still seems to be wearing bicycle shorts. And she looks absolutely overjoyed to be photographed with them on. It was the best performance of her entire career.

It’s not like she was nominated for anything that night, because she’s never been nominated for any Oscar. She was born in Roswell New Mexico, home to the alleged 1947 UFO crash. Maybe she still shops there, since this outfit is out of this world.

4. Geena Davis, 1992

It’s completely baffling why Davis, who had been nominated for her no-nonsense role in Thelma and Louise, would show up in a costume that was totally nonsensical. She looked half Cancan dancer, half Bo Peep in search of those missing sheep.

The dress was inspired by an occasionally resurrected fashion dating from Victorian days referred to as ‘asymmetrical’ or ‘waterfall’. It’s often more derisively named the Mullet after the hideous hairstyle of the same name.

Time Magazine concluded, “This is clearly a woman who sees the Oscars as a hilarious costume party.” On the other hand, she just started a film festival to promote women filmmakers. What’s more important?

3. Bjork, 2001

The Icelandic singer made a strong bid for All Time Worst with her famous Swan Dress. She was there to perform her nominated song “Now I’ve seen it All”, which everyone else on the red carpet must have been humming as she went by.

How many times have you looked at a friend’s horrible get up and said “I think we can fix it with a fake swan around your neck.”?

One observer came to her defense, arguing that it wasn’t a fashion disaster, it was art. Well, Andy Warhol made a works of art out of Campbell soup cans but he never wore them to the Oscars.

2. Barbra Streisand, 1969

The 41st Academy Awards were historic. The Best Actress category finished in a rare tie between Streisand for Funny Girl and Katherine Hepburn in The Lion in Winter. But she took home the worst outfit award hands down.

It was in The Age of Aquarius and Woodstock so there may have been hallucinogenics involved. The designer Arnold Scaasi convinced her to “show off how young and cute you are and forget about being elegant.”

1. Cher, 1986

But when it comes to the Greatest Fashion Fiasco of all time, it’s not even close.This completely taste-free Bob Mackie design for Cher is the winner by several converted touchdowns and looks like its reign will continue unchallenged for the foreseeable future and beyond.

Knowing her deep seated need for attention, this was likely a premeditated fashion atrocity. It seems Cher believes in the old marketing scheme that bad press is better than no press at all.

Sadly, no one interviewed the guy sitting directly behind her during the ceremony…