The Oscar Awards ceremony is arguably the biggest night of the year for many actresses. Not only do they experience the excitement that comes with a nomination (or even just by simply being in attendance), but it can also be a major fashion moment for them. While some choose to shine, others fail miserably and attract our attention for all of the wrong reasons. Here, we take a look back at some of the worst Oscars dresses of all time.
1 / 33
Billie Eilish (2022)
Billie Eilish’s voluminous black gown drowned the singer. From the enormous ruffled train to the off-the-shoulder layered ruffled silhouette, the dress swamped the 21-year-old.
2 / 33
Jada Pinkett Smith (2022)
The 2022 Oscars were one of the most talked about Academy Awards (remember when Will Smith slapped Chris Rock on stage?), and partly for this dress on Jada Pinkett Smith (sorry not sorry, Will). The long-sleeved emerald Gaultier gown cascaded from a ruched bodice to a full, ruffled skirt that was just too much and over the top. Plus, it looked incredibly stiff and heavy.
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3 / 33
Kristen Stewart (2022)
We appreciate the bold choice Kristen Stewart made for the 94th Academy Awards, but we’re not really into this look. Although Stewart was nominated for Best Actress, we think this is not a Best Dressed look. The tiny shorts with matching suit jacket by Chanel didn’t stun in the way we hoped.
4 / 33
Emerald Fennell (2021)
We are a bit confused about this floral Gucci gown for Emerald Fennell. The dress would be perfect for going to brunch with friends, not hitting the red carpet at the Oscars. Also, the print feels way too springtime for such an iconic event, and we would have loved to see the Best Original Screenplay winner in something more exciting.
5 / 33
Amanda Seyfried (2021)
We absolutely love this bold red colour for Amanda's dress, but the pleats aren't doing it for us. It looks like the dress is wearing her, rather than her wearing the dress, and the dramatic flared bottom looks like it's swallowing her up.
6 / 33
Margot Robbie (2021)
There's no doubt that Margot Robbie is stunning, but this dress just isn't doing it f. The silver reminds us of tinfoil, and the floral print doesn't feel glam enough for the Oscars.
7 / 33
Kristen Wiig (2020)
We get it — Kristen Wiig is a funny lady — but her dress shouldn't be the punchline. The gloves give the look a true crime feel and the shoes are confusing. It's an uncomfortable-looking outfit, let's be honest.
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8 / 33
Laura Dern (2020)
With a late '90s and/or early 2000s vibe, this black tassels and pale pink dress misses all the marks. Nothing is especially flattering and nothing feels right when looking at it.
9 / 33
Lea Seydoux (2020)
From the awkward drop of her dress to the uncomfortable neckline, this dress would have failed in 1963, 1974 and any year Lea tried to wear it.
10 / 33
Rachel Weisz (2019)
Look, we get that she's always trying to be fashion-forward with her choices, but good golly, this shiny rubber rain-slicker capelet and flowery pleated skirt are almost unforgivable. (Not totally, because we still love her, but pretty close).
11 / 33
Linda Cardellini (2019)
For most of awards season 2019, Cardellini played it safe. Nothing too boring, yet nothing super exciting either. Then she must've lost a bet for Oscar night and was forced to wear the loudest, angriest dress she could find. Yes, "angry" isn't typically used to describe a garment, but this one is clearly swallowing her whole and once done, plans to hunt down its next victim.
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12 / 33
Kacey Musgraves (2019)
This is the baby version of Linda Cardellini's dress. And those tiers and shoulders definitely look stabby.
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13 / 33
St. Vincent (2018)
In 2018, St. Vincent stepped out in a downright wacky LBD. Though we hand it to her for testing out a much bolder choice than the long, embellished gowns nearly everyone else opted for, we can't help but wonder if the huge single puffy sleeve is supposed to be making up for the missing bottom half of her dress?!
14 / 33
Salma Hayek (2018)
This sparkly lavender pleated number was a questionable choice for the 90th Academy Awards. From the colour and cut to the chain detail spread across her chest, it was a total fashion flop for Salma Hayek that year, who doesn't need this much embellishment to look glam.
15 / 33
Andra Day (2018)
Singer Andra Day served up an over-the-top floral-print getup you simply could not miss on the red carpet. The drop-crotch makes it look more like a pantsuit than an Oscar-worthy dress (with the bizarre seam placements leaving us scratching our heads). She looked like she was swimming in it! Her whole look was extra (and not in a good way).
16 / 33
Charlize Theron (2010)
We struggled with including this lilac Dior dress Charlize Theron wore to the 82nd Academy Awards in 2010. We didn't think it was possible for Dior to do wrong, but rose buds should never be applied to boobs – or anywhere, for that matter!
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17 / 33
Stacy Kiebler (2010)
Clearly, retired professional wrestler Stacy Keibler learned nothing from Charlize Theron's faux pas. Even George Clooney couldn't distract us from the massive gold rose coiled on the hip of her Marchesa gown.
18 / 33
Whoopi Goldberg (2009)
No one would ever call Whoopi Goldberg a trendsetter. It's not that we're trying to be mean, but this outfit is just one of many fashion blunders we have spotted over the years.
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19 / 33
Jennifer Hudson (2007)
Jennifer Hudson’s red carpet look in 2007 wasn’t the best, and the Oscar-winner also knew it. The brown Oscar de la Renta dress with gold bolero was reportedly Vogue’s editor Andre Leon Talley’s idea. The whole look was unfortunately not flattering and did nothing for the actress and singer.
20 / 33
Anne Hathaway (2007)
It's impossible to ignore (or forget) Anne Hathaway's 2007 Oscar dress: the year of the bow! As if the oversized boob bow wasn't enough, there's another one on the back of the dress just below her rear.
21 / 33
Tilda Swinton (2008)
To say that Tilda Swinton has a unique sense of style would be an understatement. The woman does androgyny like nobody's business – which is fine with us! What isn't fine is this lumpy, velvet sack she wore to the ceremony in 2008.
22 / 33
Uma Thurman (2004)
No one is debating whether Uma Thurman is beautiful enough to be a Grecian goddess, but that doesn't mean she needed to dress like one. Sorry Uma, but Christian Lacroix really let you down this time.
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23 / 33
Halle Berry (2002)
Many people claimed that Halle Berry was the best-dressed actress on the red carpet at the 74th Academy Awards. We beg to differ. Even Elie Saab couldn't make us fall in love with this hip-enhancing mermaid skirt over a floral sheer bodysuit, reminiscent of retirement home rugs.
24 / 33
Faith Hill (2002)
Rewind back to the early 2000s when this look was just as ew as it is today. The singer's rainbow gown hit all the wrong notes.
25 / 33
Gwyneth Paltrow (2002)
These days, it's pretty rare to see Gwyneth Paltrow take a red carpet fashion misstep, but in 2002 her gauzy tank with no bra and massive taffeta skirt was doing her no favours.
26 / 33
Probably one of the most memorable Oscar dresses (for all the wrong reasons), Bjork's swan dress is still making appearances at Halloween parties.
27 / 33
Angelina Jolie (2000)
Angelina Jolie has come a long way since she arrived at the 72nd Academy Awards looking like a gothic princess. Pair this with the awkward make-out session she had with her brother and we'll agree that this was a red carpet mishap we're happy to forget.
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28 / 33
Celine Dion (1999)
We've seen her wear her fair share of over-the-top looks over the years, but who could forget the backwards tuxedo jacket Celine Dion sported in 1999 when she was nominated for Best Original Song for "The Prayer" (from the animated film Quest for Camelot)? Sure, it's not technically a dress but had we known this was the outfit she was going to choose, we would have hoped for rain or some sort of spill that would have prevented her from actually wearing this to the show.
29 / 33
Repeat offender Cher graced the red carpet again in 1998 wearing another Bob Mackie creation. Though we'll admit, the dress had some redeeming qualities – cape aside – we just couldn't get on board with the frilly visor or lace choker.
30 / 33
Geena Davis (1992)
The bustier and ruffled bubble skirt/train combo, with the black spaghetti straps and hosiery and the long white gloves made this outfit an all-around doozy. Oh, the '90s.
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31 / 33
Kim Basinger (1990)
Poor Kim Basinger probably thought she looked edgy when she strolled across the stage at the 62nd Academy Awards. She claims to have designed the horrific Jekyll-and-Hyde-like wedding dress herself.
32 / 33
Demi Moore (1989)
Sure, it was the '80s, but that's still no excuse for bicycle shorts and an embroidered corset top with peekaboo bra. If it weren't for all the metallic features, we would've totally believed she stole this from Elvira's closet.
33 / 33
We're not sure if we should blame Oscar-winning diva Cher or Bob Mackie for designing this sartorial nightmare. Bared belly buttons and fake hair are two things that should never make their way onto the red carpet – unless it's on Halloween!
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Written ByDenette Wilford