The Most Controversial Celebrity Dresses of All Time

Jasmine Dior
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A dress can be just a a dress, but sometimes it's more. A dress can spark rumors about a relationship, or it can show the world a person's political beliefs. It can be an expression of identity, or it can just be a way to get people talking. From Old Hollywood to today, here are some of the most controversial, unique celebrity dresses of all time.

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Marilyn Monroe on a movie set in 1954

The white dress scene from The Seven Year Itch is one of the most memorable movie moments of all time. But, apparently, this white dress also played a role in Marilyn Monroe's divorce from Joe DiMaggio. He reportedly stormed off the set during filming, because he felt it was an "exhibitionist" scene. Not long after, Marilyn filed for divorce.

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Jayne Mansfield at a 1957 party

Sophia Loren was pictured giving some serious side-eye to Jayne Mansfield when she entered a Paramount Studios party in 1957 wearing this low-cut dress. Loren said of the famous photo, "I’m staring at her nipples because I am afraid they are about to come onto my plate. In my face you can see the fear. I’m so frightened that everything in her dress is going to blow — BOOM! — and spill all over the table."

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Madonna at the 1984 VMAs

This bridal lingerie-inspired look is one of Madonna's most iconic style moments of all time. It was especially scandalous because during her 1984 VMAs performance, she ended up rolling around on the floor and plenty of people got a peek at her undergarments.

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Edy Williams at the 1986 Oscars

Actress Edy Williams was known for her provocative outfits, but none stand out quite as much as this 1986 getup. Let's just say those pearls left very little to the imagination.

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Cher at the 1988 Oscars

Cher has had plenty of adventurous style moments during her career, including this daring semi-sheer Bob Mackie design she wore to the 1988 Oscars.

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Demi Moore at the 1989 Oscars

Bike shorts may have become more stylish in the last few years, but when Demi Moore wore this DIY dress/bodysuit to the 1989 Oscars, people thought it was kind of weird.

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Kim Basinger at the 1990 Oscars

Time magazine wrote, "Half menswear, half debutante gown, Kim Basinger's 1990 Oscar dress was nothing short of a white hot mess." She reportedly designed the dress herself.

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Kate Moss at the 1993 Elite Model Agency Look of the Year party

Kate Moss explained in an interview that when she wore this slip dress to a NYC afterparty in 1993, she didn't realize it was sheer. "It was the first time I really got papped. I had no idea why everyone was so excited — in the darkness of Corinne’s Soho flat the dress was not see-through!”

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Princess Diana at the 1994 Serpentine Gallery Gala

This look has come to be known as the "revenge dress," because Princess Diana wore it the same night Prince Charles spoke out publicly about his affair with Camilla. This form-fitting, off-the-shoulder Christina Stambolian dress with a hemline above the knee definitely broke a few royal style rules — and showed the world that Diana was doing just fine on her own, thank you very much.

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Elizabeth Hurley at a 1994 movie premiere

Before Elizabeth Hurley attended the Four Weddings and a Funeral movie premiere with Hugh Grant in 1994, she was pretty much unknown. But that all changed when she showed up in this plunging Versace creation held together with large gold safety pins. The dress catapulted both Versace and Elizabeth Hurley herself to a new level of fame.

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Lizzy Gardiner at the 1995 Oscars

Costumer designer Lizzy Gardiner may not be a household name, but she definitely left an impression when she wore this dress made of American Express cards to the 1995 Academy Awards. Some thought it was clever, but Cosmopolitan called it one of the worst Oscar dresses ever.

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Sarah Jessica Parker at her wedding in 1997

Sarah Jessica Parker wore a stylish black Morgane Le Fay dress to marry Matthew Broderick in 1997. In an interview, she said that if she were to do it all again, she wouldn't wear black. "I'd wear a beautiful, proper wedding dress, like I should have worn that day."

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Courtney Love at the 2000 Golden Globes

Courtney Love wore this semi-shredded dress by John Galliano to the 2000 Golden Globes. It was controversial largely because it was part of a couture collection that was "inspired" by Paris' homeless population, which some felt was insensitive to those who actually experience homelessness.

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Jennifer Lopez at the 2000 Grammys

The former CEO of Google shared that there were so many searches for photos of this dress after J.Lo wore it, that it inspired the company to create Google Images. Lopez wore a version of this dress again in a 2020 fashion show for Versace, and she looked just as stunning as she did 20 years ago.

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Björk at the 2001 Oscars

Ah, the swan dress. This was one of the more memorable and puzzling style choices ever to grace the red carpet. TV fashion critic Steven Cojocaru reportedly said it was "one of the dumbest things I've ever seen" and Joan Rivers said that Björk "should be put in an asylum." But as Björk herself said: "It's just a dress."

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Toni Braxton at the 2001 Grammys

Braxton bared lots of skin in this Richard Tyler design that she wore to the 2001 Grammys. Although it was a successful night (she won the Grammy for Female R&B Vocal performance), one critic wrote that the dress "made the attractive Braxton look as though she had yards of toilet paper stuck in all the wrong places."

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Macy Gray at the 2001 MTV VMAs

Macy Gray used the 2001 VMAs to promote her upcoming album in a very literal way. One writer for MTV.com said of the ensemble, "She looks like a Jo-Ann Fabrics (or Mood, for those of you Project Runway fans out there) threw up all over her, and then she held the whole mess together with industrial-strength paper clips." Yikes.

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Gwyneth Paltrow at the 2002 Oscars

Gwyneth herself expressed some regrets about this red carpet look. In a post for Goop several years later, she said, "I still love the dress itself but I should have worn a bra." She may have loved the dress, but critics didn't. One Guardian writer wrote, "The usually chic Gwyneth Paltrow came a cropper in a tacky transparent black vest by Alexander McQueen. Her gap-year plaits, goth eye make-up and clunky jewellery were more Camden Market than red carpet."

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Lady Gaga at the 2010 VMAs

Lady Gaga has always been known for her outlandish style choices. But there was one dress that was especially controversial: The meat dress she wore to the 2010 MTV Video Music Awards. In an interview, Lady Gaga explained, "It has many interpretations, but for me this evening ... If we don't stand up for what we believe in and if we don't fight for our rights, pretty soon we're going to have as much rights as the meat on our own bones. And I am not a piece of meat."

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Lady Gaga at a Philip Treacy show in 2012

There was some controversy around this hot pink burqa-like dress that Lady Gaga wore at a Philip Treacy fashion show in 2012. An article published in The Atlantic accused Lady Gaga of "fetishiz[ing] the women of another culture in order to sell records."

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Kate Middleton at the Thames Diamond Jubilee Pageant in 2012

Kate Middleton wore this bright red Alexander McQueen dress to an event where the rest of the royal family was wearing more muted colors. The Daily Mail wrote a pretty harsh article accusing her of trying to "steal the show."

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Kim Kardashian at the 2013 Met Gala

When Kim Kardashian attended the Met Gala for the first time in 2013, she wore a stretchy floral dress made by Givenchy. Pretty quickly, social media lit up with people criticizing Kardashian's look and comparing her dress to a couch. Robin Williams even joined in with a Mrs. Doubtfire joke. Kim later said in an interview, "I was crying the whole way home. Because I just couldn't believe it. There were all these memes about me and this couch."

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Selena Gomez at the 2013 MTV Movie Awards

While performing her song "Come and Get It," at the 2013 MTV Movie Awards, Selena Gomez wore a bindi and an outfit that appeared to be Bollywood-inspired. Hindu statesman Rajan Zed said of the performance, "The bindi on the forehead is an ancient tradition in Hinduism and has religious significance ... It is not meant to be thrown around loosely for seductive effects or as a fashion accessory aiming at mercantile greed. Selena should apologize and then she should get acquainted with the basics of world religions."

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Katy Perry at the 2013 American Music Awards

Katy Perry brought a "geisha-inspired" look to her performance of "Unconditionally" at the 2013 American Music Awards. Nolan Feeney at The Atlantic criticized her performance, writing, "It’s these kind of stereotypical visuals that plays into white fetishization of Asian women — something Perry doesn’t have to deal with when she takes off her costume."

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Anne Hathaway at the 2013 Oscars

Critics had a lot to say about this pale pink Prada dress that Anne Hathaway wore to the 2013 Academy Awards. One writer called it "simultaneously bland, confusing, ill-fitting, and vaguely inappropriate." Turns out, it wasn't Anne's first choice either. She had another dress picked out, but found out shortly before the Oscars that her Les Misérables costar Amanda Seyfried was going to wear something almost identical. So she wore this instead, to the horror of fashion bloggers everywhere.

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Rihanna at the 2014 CFDA Fashion Awards

There are "naked" dresses, and then there's the naked dress Rihanna wore to the 2014 CFDA Fashion Awards, which left almost nothing to the imagination. But as the singer herself said during the awards ceremony, “You will never be stylish if you don’t take risks.”

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Miley Cyrus at the 2015 MTV VMAs

As the host of the 2015 VMAs, Miley Cyrus had several outlandish outfits she wore throughout the evening. This dress (if you can call it that) by Atelier Versace was her first ensemble of the night.

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Blac Chyna at the 2015 MTV VMAs

Model Blac Chyna appeared at the VMAs in 2015 wearing a dress emblazoned with words like "whore" and "gold digger." Fellow model Amber Rose wore a matching suit. Blac Chyna explained in a red carpet interview, "[We] basically wanted to paint a picture of what everybody, kind of like, already says about us."

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Katy Perry at the 2015 Met Gala

This Moschino dress Katy Perry wore in 2015 became the subject of controversy after street artist Joseph Tierney (also known as "Rime") brought a lawsuit against the designer saying that they stole his artwork.

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Aunjanue Ellis at the 2016 NAACP Image Awards

Actress Aunjanue Ellis wore this statement-making dress to the 2016 NAACP Image Awards. The dress was emblazoned with "Take it down Mississippi," which was a reference to the the use of the confederate battle emblem on the official state flag at the time. In 2020, lawmakers voted to change Mississippi's state flag.

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Rihanna at the 2018 Met Gala

The theme of the 2018 Met Gala was Heavenly Bodies, and Rihanna certainly delivered in this beaded John Galliano dress and matching pope-inspired headpiece. But not everyone was a fan. Some people on social media slammed Rihanna, saying the outfit was "so offensive" and made "a mockery of Christian religion."

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Meghan Markle at the 2018 Trooping the Colour parade

Meghan Markle has been known to break some of the British royalty's rules when it comes to fashion. This chic Carolina Herrera dress she wore to the Trooping of the Colour parade in 2018 was admired by many, but others critiqued her for breaking the rules by baring her shoulders, which supposedly was seen as drawing attention away from the Queen.

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Meghan Markle at a 2018 performance of 'Hamilton'

Meghan Markle was the subject of fashion controversy yet again when she wore this modern black tuxedo dress from Judith and Charles to a 2018 performance. Some UK tabloids criticized the look, because she broke two of the supposed style rules for royals: The hemline hit above her knee and she neglected to wear nude tights underneath the dress.

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Meghan Markle at the 2018 British Fashion Awards

Meghan Markle supposedly broke royal protocol again in December 2018, when she wore this off-the-shoulder Givenchy gown. In an interview with CNBC, a former butler to the family explained that black clothes in the royal family are usually reserved for mourning, and that dark nail polish is an "absolute no-no."

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Scarlett Johansson at the 2018 Met Gala

This dreamy dress Scarlett Johansson wore to the 2018 Met Gala raised some eyebrows. The gown was designed by Marchesa, the line founded by Harvey Weinstein’s ex-wife Georgina Chapman. This event marked the first time a major celebrity wore Marchesa to a red carpet event after the Weinstein allegations broke.

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Joy Villa at the 2019 Grammys

Singer Joy Villa has chosen some unusually political outfits for her red carpet appearances, including this "Build the Wall" dress she wore to the 2019 Grammys, as a message of support for then-President Trump's plan to build a wall on the US-Mexico border.

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Kim Kardashian at the 2019 Met Gala

Kim Kardashian turned heads at the Met Gala again in 2019 while wearing this sheer beaded dress made by Thierry Mugler. This dress was considered controversial because in addition to being very sheer, people just could not believe Kim's waist was really that small. Turns out, the secret was a tight, custom-made corset and a rigorous exercise schedule.

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Billy Porter at the 2019 Oscars

Pose star Billy Porter turned heads when he arrived at the Academy Awards wearing this incredible Christian Siriano design. Speaking to Vogue about the dress, he said, "My goal is to be a walking piece of political art every time I show up. To challenge expectations. What is masculinity? What does that mean? Women show up every day in pants, but the minute a man wears a dress, the seas part."

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Joy Villa at the 2020 Grammys

Joy Villa chose another pro-Trump dress for her appearance at the 2020 Grammys. The back of the dress said "impeached and re-elected," referring to Trump's initial impeachment trial.

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Natalie Portman at the 2020 Oscars

Natalie Portman used her Oscars outfit by Dior to call attention to the fact that the year's Best Director nominees were all men. Along the lining of her cape, she had names of female directors embroidered in gold. She explained ahead of the ceremony, "I wanted to recognize the women who were not recognized for their incredible work this year in my subtle way."

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