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20 Worst Oscars Looks That Still Confuse Us

When celebrities step onto the red carpet, you better believe they do it with style. And when it’s the Oscars red carpet, that’s when all the feathers and the jewels come and all the celebs try to look their very best. It’s their night, after all. It’s when all the media and the fans are watching, judging and basically figuring out who was the best dressed and the worst dressed.

There have been some memorable moments at the Oscars. There was Jennifer Lopez’s gravity-defying green dress that showed more than it hid, and who can forget Angelina Jolie’s leg flashing black dress at the Oscars that not only had a million memes posted in its honor, but her leg got its own identity and fan page? There was also Jennifer Lawrence’s famous tumble at the Oscars – in a pink dream of a dress that we’d take a thousand falls for. If you want to know about upcoming red carpet fashion for the year, then it is the Oscars red carpet where you will find all the fashion hits, misses as well as faux pas and foibles. So we talk about the same page today – fashion-conscious and fashion-forward celebrities who somehow managed to make an epic fail of themselves at the Oscars red carpet. The Academy Awards is no place to experiment with fashion but sometimes these celebs managed to second-guess themselves and their fails are registered for posterity on the world wide web forever! Here are the ugliest and weirdest dresses seen at the Oscars’ red carpet – and we hope to never see such fashion fails ever again.

20 Gwyneth Paltrow’s Epic Fail

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Gwyneth Paltrow is usually one of the best-dressed celebs on the red carpet. An amazing physique with an epic fashion senses means she is very often the epitome of fashion and the newbie starlets in Hollywood should be taking notes from this lissome blonde. That is, excluding the 2002 Oscar mistake that Paltrow made. It wasn’t as if what she was wearing was from the flea market – quite the opposite in fact. The Alexander McQueen dress was a coveted one but somehow was terribly ugly. It has a sheer and sleeveless bodice with a pleated black skirt with a long train. While the dress may have looked good on the couture stage, amidst the glittery presence of the red carpet, it made Paltrow look wan and worn out. The earrings and necklace did nothing for her and even her makeup seemed rather meh… The Grecian braids were the only saving grace but it was a clear case of too little and too late.

19 Kate Hudson Was A Texan Lampshade

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Kate Hudson is usually an A-lister on the red carpet, even though we don’t really see her on the silver screen much anymore. But in 2001, she made not one but many fashion fails on the red carpet. One, she wore a form-fitted gown in an unflattering color and far too many tassels. Then she wore her hair in a weird gelled and curled updo. Then she put on gobs and gobs of silver-toned makeup that did nothing for her. 2001 was her single and only nomination. If the disappointment of not having won the statuette wasn’t enough, the then 21-year-old found herself on the worst-dressed list the next morning and this dress of her made her stay ever since. She said, "It was my first and only nomination. I was 21 years old and to have Stella McCartney dressing me – well I felt like the hippest, coolest girl in the world. I woke up the next morning to find out I was on every Worst Dressed list possible.” Hudson, of course, called Stella and laughed it off!

18 Demi’s Moore’s Self-Designed Disaster

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In 1989, Demi Moore was the biggest actress around. While her blockbuster Ghost wasn’t out yet, she was already a popular actress married to Bruce Willis and was steadily climbing up her career ladder. So when she stepped out on the red carpet of the 1989 Oscars in her own creation, she was making a bold move. She wore a hybrid dress/bodysuit that she herself had made from spandex bike shorts, a corset, and a metallic floral-print fabric that was tacked on as a layered bra and a train. In the picture, Demi Moore is obviously preening to all the attention and we see a lot of smiles around. The next morning the press jumped on Moore for stepping out in a bizarre self-made dress at such an important event. She did not care, being Demi Moore, and seemed to enjoy all the attention her little cut-and-sew creation was getting. Her fashion sense may have been ridiculed then but if you look closely at today’s ramps, you might end up thinking that she was simply 30 years early with her creation!

17 Kim Basinger Pulled A Jackson

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Apparently, Demi Moore’s 1989 bold dress really inspired Kim Basinger. The next year, we had the joy of seeing Basinger don a really dreadful satiny-white concoction of her own making. At 37, Basinger was at this time at the height of her career. Success goes to people’s head in weird ways and with Basinger, it was her personal touches on an otherwise boring dress. She looked part Frankenstein’s bride with her put-together monstrosity of a dress and part Miss Havisham. The satin ball gown had one side of a popped collar, with the bodice slashed down to the waist at the other end. It had strange embroidery on one arm and the other arm sported a white arm-glove in a Michael Jackson kind of style. Her blonde hair cascaded on one end and she sported red lipstick – the verdict was a resounding look of confusion. Basinger could have and should have done much better than this.

16 Uma Thurman’s Dress Seemed Confused

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For the 2004 Oscar red carpet Uma Thurman donned a Christian Lacroix – now think of tall and leggy Thurman in an elegant dress and visions start to form. Except that in 2004, it was a nightmare. Part Swiss milkmaid and part billowy curtain, the dress should never have been made, or seen in the public eye. Everything about the dress just flopped – the bodice was made for Mama June and the skirt was just confused. It billowed here and there and even Thurman’s leg flashes could not add any saving grace to such an ugly dress that could not have made anyone look good. The sleeves billowed strangely and the blue waist sash just hung there, unsure of whether it needed to be cinched or not. Thurman’s makeup was fine but added nothing to her appeal and the layered necklaces looked even more bizarre with the white sack she was wearing.

15 Charlize Theron And Her Awkwardly Placed Rosettes

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For all of us who thought that at least Charlize Theron could do no wrong, well, in 2010, we were all proved wrong. The mauve John Galliano for Dior gown called out attention for all the wrong reasons. The color and the fit were fine but there were lavender rosettes on the bodice that just looked very, very strange. The same fabric of the rosettes was used to make a very bulky train at the back that failed to add any appeal to the dress. Various fashion websites called her various things including “Madonna going to prom” but Theron did not really care. In fact, she adamantly said in response that she loved the dress. So much for the fashion police since Theron refused to be coaxed into any kind of regret of her ill-dressed curves! The starry earrings were a big save as was the makeup but other than Theron, no one liked the dress.

14 The South Park Creators Made A Bold Statement 

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South Park creators Trey Parker, Marc Shaiman and Matt Stone showed up at the Academy Awards of 2000 in complete disgrace. Parker was nominated for his song “Blame Canada,” co-written by Shaiman and trio, for some reason decided to step out on the red carpet in some interesting outfits. Parker dressed as Jennifer Lopez – repeating a cheap version of the iconic green Versace silk chiffon dress that she had worn to the 42nd Grammy Awards ceremony in 2000. Shaiman dressed as faux-fur covered disaster. Stone decided to emulate Gwyneth Paltrow and wore the prom version of her iconic pink Ralph Lauren dress, which she had worn to the 71st Academy Awards in 1999. Most of the celebrities were shocked and some were pretty vocal about their feelings. However, the trio did not care. And if you think this was bad, they had originally planned to wear duck costumes, complete with bills and all.

13 When Celine Dion Flipped A Dior

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In 1999, Celine Dion strutted onto the red carpet of the Oscars in what a fashion critic dubbed as “a profusion of confusion!” She wore a Dior lady-tux that seemed to have a surplus of fabric – of course, we could argue that Dior had foreseen the popularity of the boyfriend blazer by like a decade and a half – but that’s still no excuse for wearing it backward. Maybe Dion lost the blouse she intended to wear with it, or found it far too daring to be worn just as right side up – but normally, you don’t do something like that to an outfit by Dior. And that’s what Dion did – she wore the blazer backward and then added to it a jauntily tipped fedora, studded sunglasses, and a devil-may-care attitude. We loved the sass, yes, but the blazer was so bad. The only saving grace is that Celine’s frame, the blazer adds a certain charm. So if there was someone who could flip a Dior and get away with it, it's Dion!

12 Lizzy Gardiner Wore A Movie Reject

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Lizzy Gardiner and Tim Chappel were the costume designers for the 1994 movie The Adventures of Priscilla, Queen of the Desert. Gardiner chose to attend the red carpet of the 1995 Academy Awards in a creation of her own, which was co-incidentally a reject from the film’s wardrobe. Apparently, even fictional people refuse to wear a dress fashioned out of 254 expired American Express gold cards. Of course, all eyes were on Gardiner, considering she and Chappel won the golden statuette as well, weirdly dressed as she was. Her “excuse” or “justification” of the dress to the media was a simple “I’m broke and didn’t have anything to wear.” We are not sure why this was her emergency go-to look. After this, we are sure that Amex gave her an honorary card!

11 Geena Davis’s Bo-Peep Get-Up

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Geena Davis showed up at 1992 Academy Awards in a Little Bo-Peep dress, and it looked like she had lost most of her dress along with her sheep. The white satin dress had an uber-fitted corset that highlighted her physique, but it was the high-low ruffled skirt that caught and held those stares. Reminiscent of a can-can dress, Davis looked very happy with her outfit – that 100-watt smile shows it all. She may have been making the worst-dressed Oscars list ever since, but Davis did not care. Mary Ellen Fields, the associate of designer late Bill Hargate, says about the dress, “She never took those things too seriously. She was going for something with a sense of humor and different from everyone else.” And so Geena Davis did an iconic thing by wearing that dress – she didn’t take herself or the red carpet too seriously, and that’s probably what many celebrities could take all that well.

10 Jennifer Connelly’s Thrift Store Look 

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Jennifer Connelly’s dirty dishwater green dress turned out to be a double whammy for her. First, the dress was barely staying up on her slim frame and seemed to be slipping down while she walked on stage. Secondly, either she had a cold or her stylist was having a very off day – the pale straw-colored scarf on her neck worsened the already dull and drab dress. Surprisingly the gown was a Balenciaga, but it made Connelly look shapeless and drab. She may have won the Oscar for Best Supporting Actress for A Beautiful Mind, but in no way did that dress do anything for her, other than making her look like a mess. The neutral makeup and lack of bling did her no favors either. We hope that Connelly never pulls off a stunt like that – a beautiful woman like that should be wearing beautiful clothes, period.

9 Juliette Binoche’s Dated 20s Look

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Juliette Binoche is one very pretty woman, especially when she plays dress up. But at the 2001 Oscar red carpet, her ensemble fell short of looking good. A black halter-neck corset was paired with a black short skirt with a floor-length train on one side, and knee-length boots with strappy cutouts. She wore fingerless arm sleeves with the ensemble and multi-stranded pearl necklaces that fell about her in contrived mess. A very 1920s hairstyle completed the look – with a gelled side parting and the works. As pretty as she is, the outfit did not do anything for her and looked uncomfortably contrived, though it was a Jean Paul Gaultier look. She may have the sass to carry it off, but some dresses are just too bad to look good on even the best of bodies and attitudes.

8 James Franco Channelling Marilyn Monroe 

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Having Anne Hathaway and James Franco host the 2011 Academy Awards was basically a mistake, start to end. From Franco’s lack of enthusiasm to Hathaway’s overenthusiastic monologue – the actors got a lot of flak for doing what they did on the Academy stage. The most cringe-worthy moment, Hathaway in a tux and Franco wearing Monroe’s iconic pink dress of the movie, Gentlemen Prefer Blondes. Was Franco happy with appearing in drag? Absolutely not. Said Franco later, “I was so pissed about that, I was deliberately going to fall onstage and hopefully my dress would fall off or something – they couldn't blame that on me," He said that he felt trapped in the material and felt it was simply not his thing to do. The discomfort is apparent; he’s not that great an actor yet. Men in drag on the red carpet is never a good idea – let’s hope not to see another dude in a dress at the Oscars.

7 Zoe Saldana In Designer Pompoms

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Some fashionistas hailed Zoe Saldana’s daring Givenchy Couture gown as a fashion-forward move. The gown begins well with an embellished bodice that Saldana looks great in. But after the crystal corset ends, the mess begins. A swath of silly fabric forms the bottom half of the bodice and falls down in a loosely fitted skirt. The skirt further ends in layers of ruffled tulle in ombre-shading and somehow ends up looking like a pompom octopus instead of a trail. Presented at the Riccardo Tisci's spring 2010 Paris runway, the gown also had a bow and a trail at the back – made in the same sparkly fabric as the bodice. A chunky ring and some bling at her ears looked nice, and the casually pulled-back ponytail looked pretty. All looks good, except the tulle trail that could have made her trip, but surprisingly didn’t.

6 Is That A Swan? Nope, Just Bjork

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2001 was a year of many firsts. Gladiator came out and everyone realized that Russell Crowe could indeed act and look great while he did it. So everyone wanted a glimpse of the new macho man, but Bjork stole his thunder. How? By wearing a swan as a dress. Or rather a dress that was a swan. It’s too crazy for words. Especially when she decided to lay eggs on the red carpet as well, much to the chagrin of many a vegan and vegetarian there. The dress was not some kind of disaster that she made herself. Nope. It was an actual dress designed by Macedonian designer Marjan Pejoski. Bjork wore an embellished body stocking underneath while the “swan” covered her essentials. Why did Bjork wear it? Well, maybe it was her swan song! Okay. We’ll stop… But it had to be said.

5 Hilary Swank Didn’t Look Swanky Enough

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When we think of Hilary Swank’s Oscar red carpet appearance, we all think of that dream of a dress in navy blue by Guy Laroche that she wore in 2005. The backless wonder is what we would call a perfect red carpet dress for the Oscars – plenty of sass and beauty in it. But just two years before this, Hilary Swank wore a pink gauzy number from Dior that was akin to a little girl playing dress-up than an actual dress. The thought process behind the dress seems clear to us –  Swank spotted a nice crystallized mini at Dior but wanted to wear it to the Oscars red carpet. But she wanted the dress to be turned into a gown instead, as minis are no longer considered red carpet appropriate. The designers at Dior must have simply gathered up some pink gauze and added a few stitches here and there. They then cinched the fabric at the waist and voila – the mini is now a gown. Only, it isn’t. And pink gauze is so not swanky!

4 Chloe Sevigny’s Oscar Failure 

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Chloe Sevigny is probably remembered more for her fashion sense than for her acting. In fact, she is considered a fashion icon extraordinaire and is a regular on best-dressed lists the world over. She has not only modelled for top designers but is also a fashion designer herself. That said, even the best do slip up and at the 2001 Vanity Fair Oscar party, Sevigny seemed to have forgotten parts of her dress at home. She wore a Chanel Haute Couture but the dress is strangely put together. It begins with a lacy shirt-bodice that’s cinched at the waist with a slim belt with bow-like ruffles on the neck. The skirt is the deal breaker. It’s a sheer fabric in black, more suitable as a mourning veil than as a dress – and features a ruffled bikini skirt to hide her essentials. Overall not an outfit for the fashion-forward, or even fashion-conscious.

3 Angelina Jolie’s Morticia Addams Look 

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Angelina Jolie won the Best Supporting Actress award in 2000 for Girl Interrupted but had they known that she’d be attending in a goth look – they might have given the Oscar to someone else. She attending this red carpet with her brother and both were dressed in all-black gothic looks. The only difference was that her brother sported blonde tresses while Angelina stuck with poker straight, hip-length tresses. If you ask us, the all-black was way too much. 12 years later, Angie wore another all-black outfit (remember her right leg?) and that was an instant hit. This overtly black and fully covered Versace gown did not do much for this beauty in her prime – so it goes to say that even the best of designers and the most popular of celebrities can make an epic fail when it comes to red carpet fashion, even at the Oscars!

2 Jennifer Lopez’s Dress Seemed Hungry

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When you wear Armani Prive you better be darn sure that you look good in it, even if you have an amazing tan, an amazing figure, and go by the name "Jennifer Lopez." For her 2010 Oscar appearance, J-Lo wore a pristine white creation by the best red carpet brand there is – Armani Prive. The dress looked pretty enough at first glance with its icy white look and a bubble-wrap kind of fabric. The fitted bust looked great on J-Lo but it’s the extra ruffles at the waist that looks as if a form-fitted dress got hungry and swallowed another dress. Very distracting, especially when Amanda Seyfried turned up at the same red carpet wearing a very similar dress minus the extra waist ruffles. Maybe Jennifer's dress ate part of Seyfried’s same fabric gown. Shouldn’t Armani Prive have given both the celebrities a heads up? That said, despite the carnivorous dress, J-Lo can do no wrong on the red carpet with that physique and her inimitable sense of style.

1 Cher’s Inexplicable Look

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Cher has outdone herself many a time at the Academy red carpet but nothing screamed “look at me now” as much as her 1986 appearance. The dress, if we can call it that, was a custom-created Robert Mackie that no but Cher could have pulled off. There was a strappy, skimpy top and a long sequined skirt that glittered as much as the flashbulbs popped. There was this really strange feathered headgear that was very witch doctor meets Star Trek as well. And finally, to put the costume all together, there was a cape, with strappy cuffs to match the strappy top. Bob Mackie recalled the meeting to discuss her dress as rather memorable: "I told Cher, 'But you can't wear that to the Academy Awards.' She said, 'I don't care. I don't want to look like a housewife in an evening gown.' She was in every newspaper the next day; she's not so dumb."

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