The Most Unfortunate Dresses To Ever Appear At The Oscars

If there’s one thing we’ve learned from the Academy Awards, it’s that making it in Hollywood has nothing to do with fashion sense. Being that all eyes are on them, you would think that celebrities would want to dress to impress. Instead, some attendees arrive looking like they’re on their way to a worst-dressed Halloween party. From the infamous swan outfit to a gown that looks like a trash bag, these ensembles put the “out” in outrageous. Read on for some of the biggest fashion fails to have ever arrived at the Oscars.

Sally Looks Like She Found This Dress On The Ocean Floor

Sally-Kirkland-2002-Oscars
SGranitz/WireImage/Getty Images
SGranitz/WireImage/Getty Images

Actress Sally Kirkland arrived at the 2002 Academy Awards looking like she found her dress while scuba diving. The beige color doesn’t do much for Sally’s skin tone, especially considering it’s shiny and wrinkly-looking.

Texture aside, what is going on with the bottom of her dress? It’s like the designer decided to pin the fabric in random areas to create as clumpy a shape as possible. To make matters worse, Sally decided to sport a golden necklace that clashes with the unfortunate shades of the dress.

Bjork’s Swan Dress Looked Like A Halloween Costume

Bjork-2001-Oscars
Jeffrey Mayer/WireImage/Getty Images and LUCY NICHOLSON/AFP via Getty Images
Jeffrey Mayer/WireImage/Getty Images and LUCY NICHOLSON/AFP via Getty Images

Ever since Bjork debuted her swan dress at the 2001 Academy Awards, the ensemble has been an ongoing gag. Not only can you purchase a replica of the outfit, referred to as a “costume,” you can make it from home!

There are countless DIY directions online that teach you how to recreate this ghastly dress. To be fair, the skirt isn’t half bad. It’s the plush toy swan head wrapped around the singer’s neck that landed this outfit in the hall of shame. The designer clearly took looking like a swan too literally.

Lizzy’s American Express Dress Was Hard To Decipher

Lizzy-Gardiner-1995-Oscars
Barry King/Liaison/Getty Images and KMazur/WireImage/Getty Images
Barry King/Liaison/Getty Images and KMazur/WireImage/Getty Images

Australian costume designer Lizzy Gardiner showed off her skills with an American Express dress she doted at the 1995 Oscars. Though the outfit was impressive in how it was made, it seriously failed in terms of aesthetics.

If there is some deeper meaning to this credit card dress, it’s completely lost on us. Lizzy did win the Oscar for her work in The Adventures of Priscilla, Queen of the Desert. Compared to the outlandish outfits in that movie, Lizzy’s ensemble looks mild.

Kristen’s Dress Looked Like A Coral Reef-Matrix Fusion

Kristen-Wiig-2020-Oscars
Steve Granitz/WireImage/Getty Images and Amy Sussman/Getty Images
Steve Granitz/WireImage/Getty Images and Amy Sussman/Getty Images

We’re not sure what compelled funny woman Kristen Wiig to decide on this outfit for the 2020 Academy Awards. It looks like the designer was researching coral reefs while watching The Matrix when they created this ensemble.

The dress wouldn’t be half bad if they just ripped off those tentacle-like embellishments on the sides. And what’s up with that red carpet tail on the back? The black gloves must have been an attempt to add class to this disastrous look. Even worse, you can clearly see the beige undergarment poking out the sides.

Anne Looked Like She Dressed Up As A Trash Bag

Anne-Sophie-Bion-2012-Oscars
Bob Riha, Jr./Getty Images and Ian West/PA Images via Getty Images
Bob Riha, Jr./Getty Images and Ian West/PA Images via Getty Images

Anne Sophie Bion may be a behind-the-scenes worker, but she still should know better than to wear this dress to the Academy Awards. In 2012, she showed up to the Oscars looking like she was headed to a Halloween party dressed as a fancy trash bag.

The color and texture are spot-on, or rather, they would be if she truly were going for the garbage look. The cinched waist only serves to make the dress look that much more like a clumpy. At least the film editor could revel in her nomination for The Artist.

Sally’s Dress Was As Colorful As It Was Confusing

Sally-Kirkland-2007-Oscars
Vince Bucci/Getty Images and Jeff Kravitz/FilmMagic, Inc/Getty Images
Vince Bucci/Getty Images and Jeff Kravitz/FilmMagic, Inc/Getty Images

We don’t mean to single out Sally Kirkland by featuring her twice on this list, but she really knows how to pick some wild Oscar outfits! This one may not look like it came from the sea, but it does look like a poorly designed parachute/ circus tent.

We’re utterly confused about where all of this colorful fabric is attached to the dress. The red “curtain” is hanging from her arm, but what about that orange, yellow, and blue sheet of fabric? And is the parsley scarf supposed to bring the ensemble together, or tear it apart?

Celine Looked Like She Was Playing Dressup

Celine-Dion-1999-Oscars
Jim Smeal/Ron Galella Collection via Getty Images and Ron Davis/Getty Images
Jim Smeal/Ron Galella Collection via Getty Images and Ron Davis/Getty Images

Celine Dion may be a fantastic singer, but that doesn’t excuse the fact that she showed up to the 1999 Oscars looking like she snuck into her father’s closet to play dress-up. The outfit looks like it’s about ten sizes too big.

If the top wasn’t open-back, we would swear that she put it on the wrong way. The hat looks like it’s about the same height as Celine’s face, and her sunglasses are lined with cheesy rhinestone stars. The ensemble is a perfect example of why trying to look cool doesn’t result in actually looking cool.

Juliette Looked Ready To Cast A Spell

Juliette-Binoche-1997-Oscars
Frank Trapper/Corbis via Getty Images and Jeffrey Mayer/WireImage/Getty Images
Frank Trapper/Corbis via Getty Images and Jeffrey Mayer/WireImage/Getty Images

Juliette Binoche may have wowed critics with her performance in The English Patient, but she didn’t impress anyone with her Wizard-like outfit. Her brown, velvet gown has such a massive collar that we’re almost convinced she cast a spell to win that Oscar.

To top it off, the dress is dragging on the ground so much so that we’re surprised she didn’t faceplant on the stage while accepting her award. The best part of this outfit is the jewelry, but even sparkling gems can’t make up for all that dreary fabric.

Jennifer’s Dress Looked More Like A Tired Rag

Jennifer-Connelly-2002-Oscars
SGranitz/WireImage/Getty Images and MIKE NELSON/AFP via Getty Images
SGranitz/WireImage/Getty Images and MIKE NELSON/AFP via Getty Images

If Jennifer Connelly put as much effort into her outfit as she did for her role in A Beautiful Mind, then we wouldn’t feel like her dress doubles for a rag. The shaggy skirt wouldn’t be half bad if the color weren’t a dirty taupe.

The shade doesn’t work well with her skin tone, but the worst part is how it clashes with the cream scarf. We’ll never understand how someone thought that accessory was a smart move. Not even Jennifer’s Oscar could brighten up this disastrous ensemble.

Susan’s Copper Dress Looked Poofy And Wrinkled

Susan-Sarandon-1996-Oscars
Steve Granitz Archive 1/WireImage/Getty Images and Barry King/Liaison/Getty Images
Steve Granitz Archive 1/WireImage/Getty Images and Barry King/Liaison/Getty Images

Susan Sarandon did such an excellent job in Dead Man Walking that she took home the Oscar. The only downside is that she did so while drowning in a poofy, copper mess. Her wrinkly dress looks like Cinderella’s gown if she rolled around in the mud on her way to the ball.

The only thing about this dress that seems intentional is how closely the tone matches the Oscar in Susan’s hands. Hopefully, she didn’t lose the award in all that fabric on her way home.

Melanie’s Snakelike Dress Wasn’t Appealing

Melanie-Griffin-2010-Oscars
Jeff Kravitz/FilmMagic/Getty Images and Frank Trapper/Corbis via Getty Images
Jeff Kravitz/FilmMagic/Getty Images and Frank Trapper/Corbis via Getty Images

Melanie Griffith’s 2010 Academy Awards dress looked the sort of thing Medusa would wear. The grey-green gown had a flowy skirt and translucent sleeves that would have been lovely if not for the snakelike pattern running throughout.

We can’t imagine what would have compelled the actress to pick such a gown. Perhaps she thought the unappealing pattern would take attention away from the boot on one of her feet and the cane she had to use while in recovery. If only she would have done what snakes do and shed that top layer, her outfit would have been a stunner.

Rachel’s Gown Was Mismatched And Bloated

Rachel-Weisz-2019-Oscars
MARK RALSTON/AFP via Getty Images and Steve Granitz/WireImage/Getty Images
MARK RALSTON/AFP via Getty Images and Steve Granitz/WireImage/Getty Images

Rachel Weisz’s 2019 Oscar outfit proves that even the most gorgeous women can’t pull off everything. This hot red dress looks like the result of chopping apart two dresses and sowing them together. The bottom is flowy and floral, while the top is taut and shiny.

We wish we could say that the clashing fabrics was the only issue, but it’s also the way the dress hangs. The skirt poofs out tremendously at the waist as though it were a maternity gown. If you compare this dress to others Rachel wore that year, it’s apparent the designer is to blame.

Kim Looked Like The Bride And The Groom

Kim-Basinger-1990-Oscars
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella/Ron Galella Collection via Getty Images

Considering Kim Basinger’s history as a fashion model, you would think that she’d be immune to such a fashion catastrophe as this one. To be fair, models wear things all the time that regular people wouldn’t dream of putting on, but this gown goes too far.

The skirt is so poofy that it looks like Kim is about to walk down the aisle in a fairytale-themed wedding. One half of the dress looks somewhat normal, with a strapless, form-fitting top and a white glove. The other half, though, looks like a cross between a white button-up and a letterman’s jacket.

Angelina Looked A Little Too Gothic

Angelina-Jolie-2000-Oscars
Ke.Mazur/WireImage/Getty Images and Jeff Kravitz/FilmMagic, Inc/Getty Images
Ke.Mazur/WireImage/Getty Images and Jeff Kravitz/FilmMagic, Inc/Getty Images

Being that attending the Academy Awards is a great honor, especially when you’re a nominee, you would think Angelina would look less gothic. Between her long, all-black gown, dyed hair, and winged eyeliner, we’re not sure if she’s about to accept an award or go to a funeral.

Angelina did end up winning for Girl, Interrupted, so perhaps her attire is meant to emulate her emotionally distraught character. Then again, it was hard to pin down what Angelina was thinking in the early 2000s.

Charlize’s Dress Didn’t Do Her Justice

Charlize-Theron-2006-Oscars
Ian West – PA Images/Getty Images and Pool BENAINOUS/LEFRANC/Gamma-Rapho via Getty Images
Ian West – PA Images/Getty Images and Pool BENAINOUS/LEFRANC/Gamma-Rapho via Getty Images

Charlize Theron is another one of those stunning actresses who you would expect could pull off any outfit. Her grace and class are so apparent that she almost does make this hideous dress look passable, but we’re not being fooled.

The black-green color makes it look like the outfit was washed too many times and has begun to lose its vibrancy. The bow on her shoulder is so massive that we can’t imagine it was comfortable sitting in a chair. And then there’s the jagged train that looks as though it was stiffened with starch.

J Lo’s Side Train Made Her Hip Look Out Of Place

Jennifer-Lopez-2010-Oscars
Steve Granitz/WireImage/Getty Images and Ian West/PA Images via Getty Images
Steve Granitz/WireImage/Getty Images and Ian West/PA Images via Getty Images

Jennifer Lopez would have stunned in this dress if it weren’t for one unfortunate detail. The designer thought it would be a good idea to pin a bundle of fabric to one side so that her hip looks entirely out of place.

Typically when dresses offer an optical illusion, it’s to flatter the person wearing it. That wasn’t the case with this 2010 gown. The blaring embellishment wouldn’t be bad if it was at her lower back and served as a train. Instead, it looks like Jennifer has the skirt of another dress stuck to her side.

Diablo’s Dress Looked Like A Cheetah-Print Curtain

Diablo-Cody-2008-Oscars
Kevin Mazur/WireImage/Getty Images and Jeff Kravitz/FilmMagic/Getty Images
Kevin Mazur/WireImage/Getty Images and Jeff Kravitz/FilmMagic/Getty Images

Diablo Cody may have won the Academy Award for her screenplay Juno, but she lost when it came to dressing for the ceremony. It looks like she grabbed a cheetah-print curtain and haphazardly threw it on, adding some jewels around the neck to make it show-ready.

The lazy gown completely overshadows the sparkly embellishments and would be better suited for a pool party than a rewards ceremony. We must say that from the neck up, Diablo looks lovely with her black hair, red lipstick, and eclectic earrings. Too bad that’s only a small fraction of the total ensemble.

Tilda Appeared To Be Wearing A Velvet Blanket

Tilda-Swinton-2008-Oscars
Jeff Vespa/WireImage/Getty Images and Kevin Mazur/WireImage/Getty Images
Jeff Vespa/WireImage/Getty Images and Kevin Mazur/WireImage/Getty Images

We all have those days when we don’t want to get out of bed. Evidently, Tilda Swinton was having one of those days when she decided to dress up in a black velvet blanket for the 2008 Academy Awards.

The solid black dress hangs like a throw blanket you’d find on someone’s couch. Leaving one side sleeveless while the other has a baggy sleeve only reinforced the lazy blanky look. From the neck up, Tilda’s bare face and lack of jewelry make it look like she genuinely did roll out of bed to collect her Oscar for Michael Clayton.

Meryl Streep Looked Like She Was Wearing Gold Gift Wrap

Meryl-Streep-2012-Oscars
Gregg DeGuire/FilmMagic/Getty Images and Frank Trapper/Corbis via Getty Images
Gregg DeGuire/FilmMagic/Getty Images and Frank Trapper/Corbis via Getty Images

When you’ve been to the Oscars as many times as Meryl Streep has, you’ve got to start getting creative with what you wear. That must be why the actress showed up to the 2012 awards show looking like a poorly wrapped Christmas present.

Her sparkly gold dress would have been lovely if it didn’t look like the designer struggled to shape the gown into something a human could fit into. We’re just relieved her win was for The Iron Lady and not The Devil Wears Prada.

Jodi’s Outfit Was Overflowing With Wrinkles

Jodi-Foster-1989-Oscars
Ron Galella, Ltd./Ron Galella Collection via Getty Images
Ron Galella, Ltd./Ron Galella Collection via Getty Images

It can be hilarious to look back on fashion trends and wonder what they were thinking. However, this fashion fail can’t be blamed on ’80s fashion. Jodi Foster’s ensemble doesn’t sit right by any decade’s standards on account of its unsightly design and profuse wrinkles.

The real kicker is the partial train clinging to the back of her dress. We’re sure the added fabric was meant to give the gown a unique design, but it looks like it doesn’t belong, which is saying something considering the entire outfit is one color.