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.

Laura Dern Transported Back To The ’90s

Laura Dern
Steve Granitz/WireImage
Steve Granitz/WireImage

Even though Laura Dern wore this gown to the 2020 Academy Awards ceremony, it looks as though she’s back in the late ’90s or early 2000s. The pale pink satin gown with black tassles isn’t doing much for the actress, aside from making her look like an unassuming extra in The Great Gatsby.

Being nominated for a Best Supporting Actress award, one would think Dern would have gone all-out glamour for the ceremony. Instead, she walked up to the podium to accept her award in a dress that can only be described as “playing it safe.”

Léa Seydoux’s Neckline Should Never Have Been Designed

Lea Seydoux
Amy Sussman/Getty Images
Amy Sussman/Getty Images

During the 2020 Academy Awards, French actress Léa Seydoux graced the red carpet in this white dress. Looking like she’s popping out of the top of a wedding cake with the weirdly full yet not-full skirt; Seydoux could have done much better for the big night.

Not to mention the odd neckline with its strangely low cutout is doing nothing for the already questionable piece of clothing. All in all, the actress’s beauty is a bit diminished by her wardrobe choice.

Linda Cardellini’s Angry Pink Dress

Linda Cardellini
Steve Granitz/WireImage
Steve Granitz/WireImage

For someone who usually plays it safe during red carpet appearances, Linda Cardellini went all out for the 2019 Academy Awards. A pink, angry-looking dress with a satin bow, this dress couldn’t have stayed in the background if Cardellini tried her hardest to stay invisible.

It’s loud, vibrant, and looks to be beyond uncomfortable. Seriously, fashion designers shouldn’t be allowed to use tulle or dress their clients in something that looks like a mix between something Elle Woods and Glinda the Good Witch would wear.

Kacey Musgraves, Aka The Princess Of Tulle

Kacey Musgraves
Dan MacMedan/Getty Images
Dan MacMedan/Getty Images

Country singer Kacey Musgraves might have been going for a princess look for the 2019 Academy Awards, but she wound up looking like a three-tier cake made out of bubblegum-pink tulle. Not only does the dress look very uncomfortable and scratchy, but how in the world was anyone able to hug the artist that evening?

The Giambattista Valli Couture gown is definitely best left on the high fashion runway and not on the red carpet. The cotton candy pink and red don’t exactly mesh well together.

Faith Hill Took “Somewhere Over The Rainbow” Too Far

74th Annual Academy Awards - Arrivals
ImageDirect CR:Frank Micelotta/ImageDirect
ImageDirect CR:Frank Micelotta/ImageDirect

AT the 2002 Academy Awards ceremony, Faith Hill graced the audience with a stunning rendition of “Somewhere Over the Rainbow.” Unfortunately, the country singer took her “theme” a bit too far, strutting down the red carpet in a rainbow Versace gown that had no place being at the ceremony.

The lacey pastel rainbow pattern did nothing for the grace and poise Hill typically exudes. While Hill’s singing hit all of the right notes that evening, this gown hit all of the wrong ones.

Geena Davis’ “Wedding Dress”

Geena Davis And This
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella/Ron Galella Collection via Getty Images

Actress Geena Davis is probably questioning her decision to go with designers Ruth Meyers and Bill Hargate for this little getup. At the 1992 Academy Awards, the Oscar nominee was seen wearing what can only be described as a Las Vegas wedding dress on the red carpet.

One hundred percent satin with a fitted corset top, black straps, a ruffled skirt, full ruffled train, and elbow-high gloves, Davis looked more prepared to stand in front of an Elvis impersonator than the Academy.

St. Vincent Or Betty Rubble?

St. Vincent
VALERIE MACON/AFP via Getty Images
VALERIE MACON/AFP via Getty Images

St. Vincent strutted down the red carpet at the 2018 Academy Awards ceremony in a different take on the classic little black dress. And that different take isn’t necessarily great. While the artist is a natural beauty, the black Betty Rubble dress looks better suited for a live-action episode of The Flintstones and less so for the Oscars.

The asymmetrical cut, satin bow, and large accent sleeve are too much to fit into one tiny dress. While the dress is trying its hardest to be classy, it looks more like a doomed Halloween costume.

Andra Day And The Seams That Went Wrong

90th Annual Academy Awards - Arrivals
Dan MacMedan/WireImage
Steve Granitz/WireImage

During the 2018 Academy Award ceremony, it was hard to miss Andra Day on the red carpet. Sporting a Zac Posen gown, the actress flaunted her baby blue and pink floral gown like it wasn’t a piece that warranted a few questions. A question such as what in the world was the designer thinking when he was stitching all of those seams?

There doesn’t seem to be rhyme or reason for some of the seams, not to mention the bunching at her knees and arms make each limb look drastically out of proportion from the rest of her body. Day deserved better.

Salma Hayek Should Have Said No To The Extra Crystals

Salma Hayek Should Have Said No To The Extra Crystals
Steve Granitz/WireImage
Steve Granitz/WireImage

Actress Salma Hayek literally sparkled on the 2018 Academy Award’s red carpet in a custom Gucci by Alessandro Michele. With one too many sequined disks, layers of dazzling crystals, and tiers upon tiers of purple tulle, the typically glam actress went a little too overboard.

This is one of those cases where less would definitely have been more. And for someone like Hayek, who doesn’t need a lot to look gorgeous, this gown was an absolute Oscar fail.

Whoopi Had A Need For Green (And Purple)

Whoopi Had A Need For Green (And Purple)
Frank Trapper/Corbis via Getty Images
Frank Trapper/Corbis via Getty Images

During the 1993 Academy Awards, Whoopi Goldberg showed her true colors. Apparently, those colors just so happen to be lime green and purple. A matching jumpsuit with a jacket doubling as a pseudo-dress and pumps, Goldberg honestly looked as though she was ready to jump into a remake of the Wizard of Oz

.. a remake that would have more modern music and dance numbers. The high collar is just giving off way too many witchy vibes for this piece to be okay for anything other than dress up.

Dior Did Wrong By Charlize Theron In 2010

Charlize Theron
Bettmann/Getty Images
Bettmann/Getty Images

In 2010, Dior Haute Couture did wrong by actress Charlize Theron, designing this lilac dress specifically for the starlet to walk down the Academy Award red carpet. Not only does the color do nothing for her paler complexion and light hair, but the train pale purple train and matching rose bud accents are just too much, even in terms of quirky Oscar dresses.

Amazingly, Theron has gone on record saying that she absolutely loved wearing this dress. Was she lying? Perhaps.

Stacy Keibler’s Hip Grew 10x That Oscars

Stacy Kiebler
JOE KLAMAR/AFP via Getty Images
JOE KLAMAR/AFP via Getty Images

Two years after actress Charlize Theron graced the red carpet with her strange rosebud gown, Stacy Keibler followed suit. At the 2012 Academy Awards, the actress arrived in a metallic gold Marchesa gown that made her hips look about ten times their actual size, thanks to a rosebud accent.

While the gold color works very well with Kiebler’s natural golden hues, the dress really isn’t doing much for her figure. Amazingly, it was love at first sight for the actress when it came to the gown. She saw it during a fashion show, tried it on, and the rest, as they say, is history.

Uma Thurman In This Greek Goddess Get-Up

Uma Thurman In This Greek Goddess Get-Up
Jeffrey Mayer/WireImage
Jeffrey Mayer/WireImage

Typically known for dazzling on the red carpet, people were floored to see Uma Thurman show up in this Christian Lacroix gown during the 2004 Academy Awards. The French designer usually has more out-there pieces, and it was exactly that reason that had Thurman going to him.

That year, Thurman wanted to make the worst-dressed list! And she did, by wearing this tulle, blue satin, and gold Greek goddess-like gown. During an interview with The Hollywood Reporter, the actress revealed that she chose the gown specifically because she knew she would be criticized for it! Mission accomplished.

Tilda Swinton’s Baggy Sack Dress

The 80th Annual Academy Awards - Show
Michael Caulfield/WireImage
Michael Caulfield/WireImage

While Tilda Swinton is known for her remarkably unorthodox style, people couldn’t get over the baggy black washed silk Lanvin gown she wore during the 2008 Academy Awards. Looking closer to a sack than an Oscar-worthy gown, the questionable piece sported a long, baggy sleeve on one side and absolutely nothing on the other.

It looked as though Swinton would take flight each time she lifted her arm! The tiny actress looked like she was being swallowed whole as she walked on stage to accept her Best Supporting Actress award.

Whoopi Goldberg, The Leopard Queen Of The Carpet

Whoopi Goldberg
Jeffrey Mayer/WireImage
Jeffrey Mayer/WireImage

The thing people have to remember about this leopard dress is that no one ever said actress and comedian Whoopi Goldberg was a trendsetter. While the floor-length long-sleeve leopard print dress is doing little to nothing for the actress, it does bring out her personality in a shining fashion — absolutely hysterical.

Who else would think to wear this type of gown to the Academy Awards? Only people with a stunning sense of humor, that’s who. And only those people would think to wear their signature shades as an accessory.

Dorothea Hurley Was Stuck in The ’80s

Dorothea Hurley Was Stuck in The 80s
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella/Ron Galella Collection via Getty Images

When your husband is a rock and roll legend, the red carpet look just has to be outrageous, it appears. At least, that’s the case for Dorothea Hurley, who looks as though she was thrown back into the ’80s during the 1991 Academy Awards.

The shoulder pads, sequined dress, cut-out sleeves, and sky-high hair might have been a good look at some point in time (maybe?) but it really didn’t have any place on the Oscars red carpet. At least she and Bon Jovi looked normal when standing next to one another.

Helena Bonham Carter Looks Like An Emotional Teenager

Helena Bonham Carter
Ron Galella/Ron Galella Collection via Getty Images
Ron Galella/Ron Galella Collection via Getty Images

While Helena Bonham Carter is known for her unique sense of style, she went above and beyond for the 1987 Academy Awards. That year, she looked like an emotional teenager who “wasn’t going through a phase” and would have rather stayed home locked in her room than on stage presenting the award for Best Documentary Short Subject.

Yes, it was the ’80s, but the velvet dress with the see-through polka dot sleeves and matching gloves were even too much for the decade. At least, too much for the red carpet.

Gwyneth Paltrow Was A Bubblegum Princess

Gwyneth Paltrow
Ke.Mazur/WireImage
Ke.Mazur/WireImage

Actress Gwyneth Paltrow’s 1999 Oscar gown got mixed reviews from fashion experts. But a lot of them agreed that the actress looked like a princess swathed in a bubblegum pink gown. Kind of plain, with not much going on; it was an interesting choice for someone who was nominated for Best Actress (an award she ultimately won that year).

And it wasn’t just the dress, but also the strange matching shawl, slicked back librarian bun hairstyle, and bedazzled choker necklace that had a lot of people scratching their heads. It wasn’t one of her finer looks.

Sharon Stone Looked More Ready For A Parent-Teacher Chat

Sharon Stone
Evan Agostini/Getty Images
Evan Agostini/Getty Images

Actress Sharon Stone did something a bit different for her 1998 red carpet look. And, honestly, it didn’t pay off. Stone opted to go high-fashion for her bottom half, choosing to wear a tight-fitting Vera Wang skit. But when it came to her shirt, Stone hopped into her husband’s closet.

Stone’s top half is clothed in nothing more than a white button-down shirt from the Gap, of all places. While she doesn’t look horrible, the actress does look a bit too casual for a high-fashion and black-tie event like the Oscars.

Hilary Swank And This Bold Statement

Hilary Swank
SGranitz/WireImage
SGranitz/WireImage

In 2003, Hilary Swank walked onto the Academy Awards red carpet in this pink tulle mishap. Under the tulle, Swank is wearing what looks like nothing more than a mini dress from Forever 21, embellished with rhinestones and accented with the tulle overlay and midsection clip.

However, this gown is actually the design of Christian Dior (sorry). She then had the bright idea to go and custom dip-dye her shows to match the pink ombre look. Thankfully, she wasn’t accepting her Best Actress award that year.