The Most Controversial Oscars Outfits Over the Decades: Past and Present

The Most Controversial Oscars Outfits Over the Decades: Past and Present

Explore the most daring and eccentric fashion choices seen on the Oscars red carpet throughout history with a nostalgic twist.

Not every outfit at the Academy Awards is a hit.

Over the years, beloved celebrities have shown that they can make fashion blunders too, despite having top designers. Some common mistakes include clothes that don't fit well, strange textures, and unusual colors. Remember Björk's infamous swan dress at the 2001 ceremony?

Fashion is a subjective matter, and we appreciate the celebrities who take risks on the red carpet. However, there have been some Oscars outfits that have garnered attention for the wrong reasons.

Here, we have compiled a list of the most controversial Oscars dresses of all time. Keep reading to see the list.

Questionable Oscars Outfits Through the Years 400 554

Questionable Oscars Outfits Through the Years 400 554

Credit: Getty Images (3)

The Most Questionable Oscars Dresses Through the Years: Then and Now 

Not every look at the Academy Awards is a winner. 

Over the years, beloved celebrities have shown us that even they can make fashion mistakes, despite having access to top designers. Some of these mistakes include poorly fitting outfits, confusing textures, and bold colors. Remember Björk's infamous swan dress at the 2001 ceremony?

While fashion is a matter of personal taste, we must give credit to the celebrities who take risks on the red carpet. However, there have been a few Oscars outfits that have raised eyebrows for all the wrong reasons. (It might have been intentional, considering we even dedicated a whole post to them.)

Below, We has rounded up the most questionable Oscars dresses of all time. Keep scrolling to see the list: 

Questionable Oscars Outfits Through the Years 399

Questionable Oscars Outfits Through the Years 399

Credit: Kevin Mazur/Getty Images

Zoe Saldana, 2023

Saldana is a timeless beauty, but her Fendi slip dress reminded Us of a night gown. The look, however, did flatter her figure and featured a pretty pink hue.

Questionable Oscars Outfits Through the Years 398

Questionable Oscars Outfits Through the Years 398

Credit: Chris Pizzello-Pool/Getty Images

Laura Dern, 2021

At the event, Laura Dern won the Best Supporting Actress award for her performance in Marriage Story. She stunned in a feathered gown by Oscar de la Renta. While mixing textures can be fun, the feathered skirt of the dress overwhelmed Dern's overall look.

Questionable Oscars Outfits Through the Years 397

Questionable Oscars Outfits Through the Years 397

Credit: Amy Sussman/Getty Images

Kristen Wiig, 2020

There was a lot going on with Wiig’s bright red Valentino Haute Couture gown that featured huge ruffles down each side.

Questionable Oscars Outfits Through the Years 396

Questionable Oscars Outfits Through the Years 396

Credit: George Pimentel/FilmMagic

Dakota Johnson, 2017

Stylist Kate Young put Johnson in a champagne-colored Gucci gown that completely aged her.

Questionable Oscars Outfits Through the Years 395

Questionable Oscars Outfits Through the Years 395

Credit: Frazer Harrison/Getty Images

Charlize Theron, 2010

Theron can usually do no wrong, but the rosette details of her Dior gown felt off.

Questionable Oscars Outfits Through the Years 394

Questionable Oscars Outfits Through the Years 394

Credit: Steve Granitz/WireImage

Uma Thurman, 2004

Thurman called this Christian Lacroix look her most “embarrassing experience.”

Questionable Oscars Outfits Through the Years 393

Questionable Oscars Outfits Through the Years 393

Credit: KMazur/WireImage

Jennifer Connelly, 2002

Connelly’s Balenciaga gown didn’t need to be accessorized with the chiffon neck scarf.

Questionable Oscars Outfits Through the Years 392

Questionable Oscars Outfits Through the Years 392

Credit: Mirek Towski/FilmMagic

Bjork, 2001

The list would not be complete without the swan dress.

Questionable Oscars Outfits Through the Years 391

Questionable Oscars Outfits Through the Years 391

Credit: Steve Granitz Archive 1/WireImage

Kate Hudson, 2001

Hudson’s Stella McCartney gown was a bit too busy with sparkles, fringes and cutouts.

Questionable Oscars Outfits Through the Years 390

Questionable Oscars Outfits Through the Years 390

Credit: Jeff Kravitz/FilmMagic

Kate Winslet, 1998

Winslet’s Alexander McQueen dress seemed better suited for a big screen role and not the red carpet.

Questionable Oscars Outfits Through the Years 389

Questionable Oscars Outfits Through the Years 389

Credit: Kevin Mazur/WireImage

Whoopi Goldberg, 1993

Goldberg said backlash of the outfit — which channeled her Cinderella character four years too early — “kept me from dressing up for a very long time.”

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