10 Celebrity Wardrobe Fails That Went Terribly Wrong

If you like celebs and fashion as much as I do, you’re in for a treat!

Unless you’re a cinephile obsessed with finding the best plot, sound effects, or cast, you have to admit that one of the most enjoyable parts of watching an award show is admiring the stars as they strut down the red carpet. Their suits and dresses often cost more than an average person’s debt, and their loaned accessories are worth more than most of us will ever see.

But as much as I love to appreciate a celeb and think about how their outfits would suit me, I must admit I also like to see their wardrobe faux pas. Call me mean, but I find it amusing, and I’m pretty sure I’m not the only one. Whether the jewelry is a bad choice, the dresses are too casual, the shoes don’t fit properly, or they’re over-accessorized, one thing’s for sure: they will go down in history (but not as they would like to, though).

If you want to see the outfits and the accessories that didn’t do them justice and put them on the list of the biggest red carpet style fails of all time, keep reading, because I’m about to spill all the tea. Here they are:

Courtesy of Pinterest

1. Madonna

The gorgeous queen of pop is known for her extravagant appearances, but no one expected to see her entire behind on the red carpet if you know what I mean. She went to the Grammy Awards in LA in 2015 wearing a spicy outfit that can be described as Matador chic, and since many people said it wasn’t red carpet-appropriate, she did something to shut their mouths: she picked up the backside of her already short corset and dress combination and flashed her moon at all the cameras behind her.

I don’t know what you think, but one thing’s certain: her response won’t be forgotten anytime soon. But what do you think about her outfit? Did you like it? I must agree with those who said it’s better for a concert.

2. Uma Thurman

Uma Thurman is one of the prettiest celebs, but the Christian Lacroix dress she wore at the Oscars in 2004 didn’t do her any justice. She knew that her high-low tulle dress, paired with a vest won’t be appreciated by many, but she didn’t care. When asked about her fashion choice, she mentioned that she didn’t want to follow the rules and wear something predictable, so she didn’t mind if she was considered the worst-dressed celeb, but she’s glad she was chosen.

…What can we say? We adore her confidence, but not the dress!

Angelina Jolie 2000 Oscars
Photo by Everett Collection from Shutterstock

3. Angelina Jolie

Angelina Jolie looks amazing in almost anything, but her Oscar appearance in 2000 was shocking for multiple reasons. First of all, she wore a long black dress accessorized with a pair of silver earrings, which added a bit of sparkle. However, her pale skin and silky black hair made her look like Morticia Addams and not at all like a glamorous actress.

The second thing the celeb did that shocked the audience was the passionate kiss she shared with her brother James Haven. Even though everyone was startled seeing them make out, the stars said it was only an encouragement and a familiar kiss, nothing crazy.

Well, that’s what they said…

4. Sally Kirkland

Sally Kirkland is a famous actress known for her role in the drama movie “Anna” (1987), but her outfit choices don’t meet her talent. She shocked both the audience and the media at the 2007 Oscars with her weird outfit. She wore a long black dress that was sheer at the top, paired with a sort of colorful cape.

We have no idea what she tried to do, but she looked like she needed to put multiple clothes on her at the airport. Sorry, Ms. Kirkland, but it wasn’t a good one!

Cher 1986 Oscars
Courtesy of Pinterest

5. Cher

There’s no doubt that Cher is both a fashion icon and a stunning singer, but even pros get things wrong sometimes. At least this is what happened to her at the 1986 Oscars. She wore a sparkly two-piece set that revealed her toned abs, and while the cape made the outfit look more glamorous, the huge accessory she had on her head destroyed the entire look. It made her look like a giant angry black bird. Not very demure and certainly not very mindful, Ms. Cher!

6. Joy Villa

Joy Villa is known for having a bold appearance when it comes to fashion, but not all of them are worth being mentioned on the good list. The singer came to the 2015 Grammys wearing a bunch of orange fencing, which made her look like a potato sack from the grocery store. Not a look to be proud of!

However, if you have a different opinion regarding her fashion choice, let us know in the comments below because we’d love to chat!

7. Robert Downey, Jr.

If you thought that only women received the title of the worst dressed celebs, you were wrong, because many men made it on this list too. One of them is Robert Downey, Jr., who wore an outdated shiny suit paired with a big blue bow at the 2010 Oscars. While he was following the decade’s trends at the moment, I still believe he looks like one of the cats from “The Aristocats.” Do you agree with me?

8. Billy Bob Thornton

Billy Bob Thornton is famous for his incredible career and eccentric personality, but his fashion choices aren’t always top-notch. At least this is what happened at the 1977 Oscars. He wore a black suit with a white shirt and vest, paired with a horrible-looking tie.

The nice touch was the blue ribbon on this chest, which shows his support for child abuse prevention, anti-bullying, and s*x slavery awareness. It seems the actor and musician didn’t prioritize his outfit and instead focused on the event, as evidenced by his ZZ Top hat.

However, he might’ve been a trendsetter, because two decades later, sporty hats are paired with elegant outfits. If you don’t believe it, just look at what Kylie Jenner wore at the MET Gala in 2022.

Lizzy-Gardiner 1995 Academy Awards
Courtesy of Pinterest

9. Lizzy Gardiner

One of the most unforgettable red carpet moments was Lizzy Gardiner’s appearance at the 67th Academy Awards in 1995. While she was celebrated for her brilliant work on “The Adventures of Priscilla, Queen of the Desert”, her revealing outfit that night left much to be desired, in my opinion.

Her golden dress was made of American Express Gold Cards, and she paired it with a long cape in the same color. On the side, the dress was split so she could walk, revealing her long and toned legs.

10. Juliette Binoche

French actress Juliette Binoche was another celeb who didn’t quite nail it with her red carpet outfit. The beautiful star showed up at the 2001 Oscars looking like a goth flapper, with an old-fashioned pearl necklace and striped tights. While the idea might’ve been good, the real result was disappointing.

And there you have it—some famous faces who didn’t quite hit the mark with their red-carpet looks. We’d love to hear your thoughts! If you liked any of their outfits, drop a comment below so we can chat! If you enjoyed reading this article and would like to check out something else from our website, this is an article you don’t want to miss: 5 Reasons Why the Democrats Chose Kamala Harris

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