16 head-turning Oscar looks that are still considered controversial today

The best Oscars looks are the ones that are still talked about decades later

Don Ameche holding the Best Supporting Actor Oscar award for his role in Cocoon, backstage at the Academy Awards with award presenter Cher, who is wearing an unusual Bob Mackie evening gown with a feather headdress.
(Image credit: Bettmann / Contributor / Getty Images)

The Oscars are home to some of the most stunning (and not so stunning) outfits of the year. The highly-anticipated night is almost here, and while we can't wait to see what the stars show up in, we can't help but look back on the looks that made (and still make) headlines.

From Barbara Streisand's see-through pantsuit to Cher's questionable feather headdress, here are the most controversial Oscar outfits that still make us do a double-take.

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1. Barbara Streisand 


(Image credit: Walt Disney Television via Getty Images Photo Archives/Walt Disney Television via Getty Images)

In 1969, Barbara took home the award for best actress for her performance in Funny Girl. What she wasn't expecting, though, was for her entire pantsuit to go completely see-through (under the right lighting).  

2. Cher

Portrait of Cher at the Oscars, wearing an outfit by Bob Mackie.

(Image credit: Frank Trapper/Corbis via Getty Images)

Cher, without a doubt, stole the show for red carpet looks during the 1986 Oscars ceremony. The look screamed Las Vegas showgirl and was the creation of her longtime collaborator Bob Mackie.

3. Edy Williams

Actress Edy Williams arrives to the 46th Academy Awards at Dorothy Chandler Pavilion in Los Angeles,California.

(Image credit: Michael Montfort/Michael Ochs Archives/Getty Images)

Edy bore everything during the 1974 ceremonies. Known for her wacky and eccentric clothing, she even brought her dog with her and landed headlines when critics deemed her outfit inappropriate for the award show.

4. Demi Moore

Demi Moore

(Image credit: Jim Smeal/Ron Galella Collection via Getty Images)

Demi rocked the biker shorts look long before they came back into style. She also decided to pair it with a Victorian-styled skirt attached at the back. 

5. Kim Basinger

Kim Basinger and brother

(Image credit: Ron Galella/Ron Galella Collection via Getty Images)

This look was a ballgown-suit combo bringing us elegance and charm as Kim walked down the red carpet for the 1990s Oscars.

6. Geena Davis

1992: Actress Geena Davis in ruffled evening dress at Academy Awards.

(Image credit: DMI/DMI/The LIFE Picture Collection via Getty Images)

Geena gave us a very bridal showgirl look in her ruffled satin-like gown – even pairing it with long white gloves for added elegance.

7. Whoopi Goldberg 


(Image credit: Frank Trapper/Corbis via Getty Images)

No, you did not suddenly transport to Oz, that's just Whoopi's glowing green and purple Oscar's fit she wore to the 1990s show. She even matched her shoes to the outfit showing us that she wasn't playing it safe that year.

8. Lizzie Gardiner

Lizzie Gardiner at the Shrine Auditorium in Los Angeles, California

(Image credit: Ron Galella/Ron Galella Collection via Getty Images)

Your eyes are not fooling you. Those are, in fact, credit cards in the shape of a dress. Lizzy designed the dress herself and reportedly used 254 expired American Express Gold cards to complete the look. The look received mixed reviews, with some women accusing her of not taking the night seriously.

9. Matt Stone & Trey Parker

Matt Stone & Trey Parker

(Image credit: SGranitz/WireImage)

These two really turned heads when they showed up in these brightly colored gowns. If the vibrant colors didn't steal your attention, then the dress styles most certainly did. You could arguably say that they stole the show that night.

10. Björk

Bjork at the arrivals at the 73rd Annual Academy Awards at Shrine Auditorium in Los Angeles, California.

(Image credit: Mirek Towski/FilmMagic)

This dress is quite literally a piece of history. In 2001, Björk stunned the world by showing up in a swan-shaped dress. People were so taken by it that it's actually preserved in museums around the globe.

11. Gwyneth Paltrow

Actress Gwyneth Paltrow attends the Vanity Fair Oscar Party at Mortons March 24, 2002 in West Hollywood, CA.

(Image credit: Sebastian Artz/Getty Images)

The following year, Gwenyth shook the crowd by ditching her soft and sweet looks for an edgy goth glam outfit that critics were speechless when she arrived. While Gwenyth today still loves the gown, she has some of her own critiques, saying she wished she had worn a bra with and toned down the makeup.

12. Sally Kirkland

Actress Sally Kirkland attends the 79th Annual Academy Awards held at the Kodak Theatre on February 25, 2007 in Hollywood, California.

(Image credit: Stephen Shugerman/Getty Images)

There was a lot going on with this look that critics even compared her outfit to a circus tent. The colorful design mixed with the black and transparent bodice really showed off everything (including her pasties).

13. Celine Dion

Arrivals at the Dorothy Chandler Pavilion in Los Angeles, California.

(Image credit: Kevin Mazur/WireImage)

Celine redefined how to wear a tuxedo by quite literally showing up in a backwards tuxedo for the 1999 Oscars. This was back when women were still strictly wearing gowns to the ceremony making Celine one of the first to step away from that tradition. While reviewers raved about the look, that year was possibly one of the most interesting in Oscar fashion history. 

14. Angelina Jolie

Actress Angelina Jolie arrives at the 84th Annual Academy Awards held at the Hollywood & Highland Center on February 26, 2012 in Hollywood, California.

(Image credit: Ethan Miller/Getty Images)

You know you've made it when your look causes a social media frenzy. Angelina was showing off the dramatic slit of her dress so much that it caused her leg to trend on Twitter. No one could ever forget her power stance, though.

15. Pharrell Williams

Musician Pharrell Williams (L) and wife Helen Lasichanh attend the Oscars held at Hollywood & Highland Center on March 2, 2014 in Hollywood, California.

(Image credit: Michael Buckner/Getty Images)

Nothing caused more of a stir than when Pharrell showed up to the Oscars wearing shorts instead of a more traditional suit. He really decided to show off his legs that year.

16. Anne Hathaway

Actress Anne Hathaway, wearing Giorgio Armani, arrives at the Oscars at Hollywood & Highland Center on February 24, 2013 in Hollywood, California

(Image credit: Lester Cohen/WireImage)

Anne's dress has received a lot of criticism over the years, not only for the illusion that her boobs were sticking out but because she was originally supposed to wear a Valentina gown but made a last-minute decision to wear this Prada gown instead.

Rylee Johnston

Rylee is a U.S. news writer who previously worked for woman&home and My Imperfect Life covering lifestyle, celebrity, and fashion news. Before joining woman&home and My Imperfect Life, Rylee studied journalism at Hofstra University where she explored her interests in world politics and magazine writing. From there, she dabbled in freelance writing covering fashion and beauty e-commerce for outlets such as the TODAY show, American Spa Magazine, First for Women, and Woman’s World.