By Wonderwall.com Editors
9:00am PDT, Mar 10, 2024
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Though it certainly wasn't boring and we appreciated the fashion risk, we couldn't fully get behind the Valentino frock Kristen Wiig wore to the 2020 Oscars. Critics dubbed it her "lasagne dress."
MORE: Best Oscars jewels of all time
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Bjork made headlines when she donned this swan dress during the 2001 Academy Awards. The costume-like ensemble by Marjan Pejoski is now one of the most iconic looks in red carpet history.
MORE: Stars who brought their parents to the Oscars
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Cameron Diaz donned this disastrous getup during the 1998 Academy Awards. It would've been bad enough for a regular night out on the town, but the fact that she wore this look on Hollywood's biggest night made it a fashion crime against humanity!
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Messy Marchesa! Heidi Klum selected this frilly purple Marchesa gown for the 2016 Academy Awards, giving us tulle-filled nightmares. Between all the extra fabric and those unnecessary floral embellishments, this one was one of the worst looks that year.
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We're still not sure what was going on with Whoopi Goldberg's 1993 Academy Awards look: a wild purple-and-lime ensemble with an open skirt.
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With its bizarre fringed neckline, the muted Stella McCartney for Chloe gown that Kate Hudson (seen here with then-husband Chris Robinson) donned during the 2001 Academy Awards, when she was up for best supporting actress for her work in "Almost Famous," belonged in a Western flick rather than at an award show, right?
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The partly sheer menswear-inspired ensemble that Barbra Streisand donned during the 1969 Academy Awards made her look like quite the "Funny Girl."
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Though we appreciated the rocker vibe, Kristen Stewart's look at the 2022 Oscars left a lot to be desired. The star arrived in Chanel — a custom black satin jacket and matching shorts. She added a white chiffon blouse that she rocked unbuttoned and pointy-toe pumps, but ultimately this look felt way too casual for such a momentous occasion.
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Kim Basinger donned a bizarre asymmetrical white ballgown during the 1990 Academy Awards. The one-sleeve dress featured a dramatic neckline with a collar on one side. She added to the oddness of the overall look by wearing one satiny opera glove on her sleeve-free arm.
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We adore Liza Minnelli. But the vintage Halston separates she donned during the 2014 Oscars? Not so much. The silky blue ensemble was far too casual for Hollywood's biggest night, and the matching streak of blue in her hair was just plain cheesy.
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If Jennifer Connelly was hoping to elevate her look during the 2002 Academy Awards — the year she won the Oscar for best supporting actress for her work in "A Beautiful Mind" — by pairing a skinny scarf with her drab drop-waist tan gown, she failed tremendously.
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The white Christian Lacroix dress that Uma Thurman wore during the 2004 Academy Awards looked like an arts-and-crafts project gone wrong.
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During the 2000 Academy Awards, "South Park" masterminds Matt Stone and Trey Parker memorably spoofed two of the most iconic looks in red carpet history: the Versace gown that Jennifer Lopez donned during the 2000 Grammys and the pink Ralph Lauren dress that Gwyneth Paltrow wore during the 1999 Oscars. (The duo later admitted that they'd taken LSD before walking the red carpet.)
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Celine Dion didn't hit a high note when she wore a white John Galliano pantsuit — backwards! — during the 1999 Academy Awards. What was she thinking?
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There was a lot of pink on the red carpet at the 2019 Oscars, but we weren't fans of Sarah Paulson's take on the trend that year. She disappointed in a Brandon Maxwell gown with an oversized bodice and unnecessary cut-outs at the waist.
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It might not seem that bad now, but Anne Hathaway topped every worst dressed list after the 2013 Oscars in this disappointment of a pink Prada column dress. The poorly constructed gown featured two points in the fabric on the bodice, which drew attention to certain body parts that Anne probably would've liked to have kept under wraps. The whole thing was just amateur hour.
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Back in 1986, Cher dressed like she was heading to a burlesque show rather than the Oscars in a black Bob Mackie number with a towering headpiece.
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The always-gorgeous Elsa Pataky had that expectant-mom glow during the 2014 Oscars, so it's a shame that she didn't choose a dress that was more worthy of her beauty for Hollywood's biggest night. Instead, Chris Hemsworth's wife donned an unfortunate Elie Saab gown with a drop waist that pulled awkwardly under her baby bump.
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Yikes. Charlize Theron's 2010 Academy Awards gown was interesting, to say the least. The John Galliano for Christian Dior design memorably featured eye-catching florets on the bodice.
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Lady Gaga ruined an otherwise stellar look at the 2015 Academy Awards with her accessories: She wore a pair of oversized red leather gloves with her gorgeous white Azzedine Alaia gown. Why? We still don't know!
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"The Favourite" star Rachel Weisz donned one of our least favorite looks of the 2019 Oscars. Her red Givenchy dress featured an edgy latex top contrasted with a feminine embellished tulle skirt, which combined for an unflattering overall look. One element of her ensemble we did like? Her unexpected diamond headband.
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Back in 1995, Australian costume designer Lizzy Gardiner unforgettably donned this dress comprised of 254 expired American Express credit cards to pick up an Oscar for best costume design for her work on "The Adventures of Priscilla, Queen of the Desert." The dress was originally conceived as a costume for the film: "I'm broke, and I didn't have anything to wear. So I went through my list of past good ideas," Lizzy reportedly said.
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Angelina Jolie channeled Morticia Addams at the 2000 Academy Awards, where she picked up the Oscar for best supporting actress for her work in "Girl, Interrupted."
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Juliette Binoche was wearing this velvet coat-dress with a massive popped collar when she won the Oscar for best supporting actress for her work in "The English Patient" in 1997.
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Hilary Swank wore a bizarre Christian Dior gown during the 2003 Academy Awards. The frock featured a spaghetti-strap minidress under a tulle overlay. Weird.
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Jennifer Hudson won big during the 2007 Academy Awards — but not because of her ensemble. Though the color of her Oscar de la Renta gown was beautiful and had one of our favorite features — pockets! — she really lost us with her metallic snakeskin-patterned bolero jacket.
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Scarlett Johansson delivered one of the most disappointing Oscar style moments of the past decade when she attended the 2017 Academy Awards in this completely unflattering Alaia dress, which she wore with a black bejeweled belt.
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Mariah Carey seriously underwhelmed during the 2010 Academy Awards in a cheap-looking asymmetrical dress that gave us major prom vibes. (Seriously, like, did she pick this up at Macy's?)
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Paul McCartney's controversial second wife, model Heather Mills, raised eyebrows when she joined him at the 2002 Oscars in midriff-baring separates: a lacy off-the-shoulder top with a matching midi-length skirt.
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Geena Davis channeled a Vegas showgirl during the 1992 Academy Awards in this dress with a high-low ruffled hemline that she wore with sheer black pantyhose.
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Two words come to mind when we think about the Lanvin dress that Tilda Swinton donned during the 2008 Academy Awards: trash bag.
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Dakota Johnson's matronly 2017 Academy Awards gown was one of the worst on the red carpet that year. The gold Gucci dress featured a train, a frilly high collar and a bizarre bow detail at the waist — all of which added up to a major miss.
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Rachel Griffiths attended the 1999 Academy Awards in an eyesore of an iridescent pink gown with matching gloves. (Hey, it was the '90s!)
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During the 2007 Academy Awards, Faye Dunaway rocked a funky black gown with a drop waist that left a lot to be desired.
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The copper color of the very poofy dress that Susan Sarandon donned during the 1996 Academy Awards matched her hair but was somehow all wrong. She completed her look with a matching shawl — because obviously more shiny bronze fabric is what this look needed!
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Faith Hill couldn't choose which pastel shade she wanted to wear during the 2002 Academy Awards, so she basically wore them all in one Versace dress.
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It's hard to go wrong with Chanel, but Sarah Jessica Parker did just that during the 2010 Academy Awards. Her gown from the design house had way too much going on in the back.
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Zoe Saldana wore a Givenchy Couture gown in multiple shades of purple during the 2010 Academy Awards. Needless to say, fashion critics were divided over this big, bold look.
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Maya Rudolph donned this disastrous Valentino design at the 2018 Oscars. Though it was edgy and unexpected, the long-sleeve dress with a turtleneck and a pleated front just wasn't the right look for such a fancy event.
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If you end up with an injury, maybe pick a dress that won't highlight it? Melanie Griffith attended the 2005 Academy Awards in this blinged-out Atelier Versace gown featuring a sky-high slit that showed off her interesting accessories: a cast and a cane.
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Sophia Loren attended the 2009 Academy Awards in a "Dynasty"-worthy monstrosity of a gown.
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Helena Bonham Carter's long legacy of wearing truly terrible ensembles during the Oscars stretches all the way back to 1987, when she donned this atrocity of an all-black ensemble — an asymmetrical tulle skirt with a bustle and a velvety bodice with a sheer, polka-dot neckline and sleeves — with no makeup and a messy updo.
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The divisive tiered Zuhair Murad gown that Miley Cyrus donned during the 2009 Academy Awards drew comparisons to a wedding cake.
