The Most Controversial Celebrity Dresses of All Time Through the Years

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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.

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.

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.”

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.

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.

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.

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!”

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.

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.

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.

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.

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.”

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.”

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.”

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.

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.”

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.

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.

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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