Worst Oscar Dresses and Fashion Choices of All Time

Take a walk down memory lane to revisit some of the worst Oscar fashion choices of all time.

Worst Oscar Dresses and Fashions of All Time

Each year, watching the Academy Awards reminds us that celebrity fashion is almost as important as the award show itself.

Unfortunately, not everyone get its right, but there is a silver lining — the worst choices are often the most memorable.

Check out some of the worst Oscar dresses and men's fashion choices ever seen on the red carpet.

St. Vincent (2018)

Musicians often have a hard time dressing for the Oscars, and St. Vincent is no different.

This is fine for the Grammy red carpet but tough to pull off at the Oscars.

Bette Davis (1936)

This Oscar outfit was no accident on Davis' part and was worn in protest. She was nominated for best actress for her role in “Dangerous," but she actually hated the film.

She reluctantly went to the award show in this plain dress after Warner Bros forced her to show up. The collar is so large because the dress was designed to look like something the hired help would wear, which is how she felt about being employed by the studio.

Helena Bonham Carter (2013)

Bonham Carter got plenty of flack for this outfit, and its made plenty of "worst dressed" lists.

However, she's got a unique style all her own, even if this dress didn't work as well as her others usually do.

Ann Margaret (1965)

Ann Margaret would have been 24 in 1965, but this outfit and styling ages her by about 20 years.

It would have also been very warm for Los Angeles, too, even in winter!

Sally Kirkland (2002)

There are way too many things going on here, least of which is the weird rhinestone Bindi jewel on Kirkland's forehead.

Billie Eilish (2020)

Eilish is still young, and this ensemble was a big misstep for an event as formal as the Oscars.

However, she really made up for it at the Met Gala just a year later!

John Travolta (2010)

Tell us you didn't feel like attending the Oscars without telling us you didn't feel like attending the Oscars.

John Travolta will go first.

Lizzy Gardiner (1995)

Gardiner won an Oscar for costume design for "The Adventures of Priscilla, Queen of the Desert."

This dress, made from 254 expired American Express gold cards, was created for the film, which it would have been great for, but the card company wouldn't authorize it, so Gardiner wore it on the red carpet instead.

Edy Williams (1986)

Actress Edy Williams starred in 1969's "Beyond the Valley of the Dolls," one of the greatest cult classics of all time on par with "The Rocky Horror Picture Show."

Williams attended the Oscars several times — so believe us when we tell you, it was hard to pick just one of her outfits for inclusion on this list.

Barbara Streisand (1969)

Streisand wore this Scaasi pantsuit (she was one of the first women to wear pants to the Oscars) proudly, but when the flashbulbs went off, the lining to this outfit didn't exactly conceal everything as intended.

In fact, it revealed more than she and the designer bargained for.

Robert Downey, Jr. (1989)

Robert Downey, Jr. with Sarah Jessica Parker

Downey Jr. became one of the worst dressed men in Oscar history with this pirate-meets-Peter-Pan ensemble.

He's thankfully grown up a bit in the past two decades.

Cher (1974)

Cher has always been one to take chances in fashion, but she looks like she should be on a beach drinking a margarita at sunset instead of walking down the red carpet.

That floral choker really makes a statement.

Demi Moore (1989)

If you didn't already know, bike shorts weren't just meant for bikes or gyms back in the late 1980s.

While it's definitely one of the decade's oddest and most unflattering fashion trends, sewing them into a gown didn't make things better.

Dennis Rodman (1997)

If Rodman had played Willie Wonka, this may have been the perfect Oscar outfit.

It turns out he didn't, and it wasn't.

Kim Basinger (1990)

Basinger is said to have designed this dress herself with a little inspiration from none other than Prince.

It's a good thing she stuck to acting.

Matt Stone and Trey Parker (2000)

Did you really think "South Park" creators Matt Stone and Trey Parker were going to take the Oscars seriously?

When asked about the dresses by reporters, they avoided the questions entirely, saying only, "It’s a magical night tonight."

Bjork (2001)

Bjork made none other than Joan Rivers mad about this dress choice. She said, "The girl should be put into an asylum."

But say what you will — this is the dress that's remembered from the 2001 Oscars.

Celine Dion (1999)

Dion's backward tux was from Dior by John Galliano. It was accessorized with a cocked Fedora and diamond-studded Ray-Bans. For all its splendor, it made dozens of worst-dressed lists.

Dion, however, remains unfazed regarding the criticism to this day: "If I would do this today, it would work. It was avant-garde at the time."

Heidi Klum (2016)

Just how much is too much lavender?

This is the answer. Klum's dress looks like it smells like a potpourri bowl.

Pharrell Williams (2016)

If he had on pants, Williams may have made a completely different list.

But shorts at the Oscars should be a big no-no. They never work.

Lady Gaga (2015)

While it's not Gaga's best look, the gown itself isn't really the issue. It's the dishwashing gloves that she decided to use as an accessory that became an instant Oscar meme.

Maybe she has a side hustle as a cleaning woman?

Diana Ross' Oscar Date (1985)

Ah, the 1980s.

We don't know who Diana Ross' date is, but his shoulder pads and full-length leather coat are a mesmerizing choice — and one of the most daring men's fashions in Oscar history.

Linda Cardellini (2019)

Cardellini's lace ensemble looks like something you'd wear when getting dressed for the Oscars back in the 1960s.

It has "old school boudoir photo" written all over it.

Jon Bon Jovi (1991)

Seinfeld's George Constanza once said, "I would drape myself in velvet if it were socially acceptable."

In 1991, Bon Jovi lived that dream.

Laura Dern (2021)

There's nothing not to love about Laura Dern (and her Oscar for "Marriage Story" was well-earned), but this dress looks like two completely different outfits sewn together in a rush.

And how many birds were compromised in making the skirt?

Kristen Wiig (2020)

Some people compared Wiig's 2020 Oscar dress to lasagna, but we think it's more David Bowie-inspired.

It's cool but not Oscar-worthy.

Kasey Musgraves (2019)

Pink was all the rage at the 2019 Oscars, and thankfully, that trend has passed.

Musgraves' outfit is saccharine sweet, as if Pepto Bismol were a dress.

Uma Thurman (2014)

Thurman's beauty outshines this dress, which looks like four different outfits — both causal and formal — sewn into one.

We actually kind of like it for a day at the beach maybe or for sailing on a pirate ship but definitely not for this formal affair.

Juliette Binoche (1996)

As we learned from Bon Jovi (and George Costanza), velvet was a big deal in the 1990s.

But this goes above and beyond with a popped collar, which is also a very strange choice.

Cher (1986)

Yes, we had to include Cher again. At this time in the 1980s, Cher had long been on the fringes of Hollywood, as people thought of her as too much of a pop icon to be taken seriously as an actress.

When she decided to attend the Oscars, she decided to make a statement — and boy, did she ever. "I thought, 'OK, you can go in a simple black dress and be just like everyone else.' But then I decided, 'I’m going to remind them of what they don’t like about me.'"

Mic drop.