The worst looks in the history of the Oscars

Some infamous looks on the most important night in Hollywood
Bjork: 2001
Tom Cruise: 1989
Bette Midler: 1982
Randy Quaid: 1974
Angelina Jolie: 2000
Wesley Snipes: 2022
Demi Moore: 1989
Jason Momoa: 2019
Sally Kirkland: 1989
Sally Kirkland: 2002
Sally Kirkland: 2007
Heather Mills and Paul McCartney: 2002
Uma Thurman: 2004
Kim and Mick Basinger: 1990
Cameron Diaz: 2002
Sebastián Yatra: 2022
Diablo Cody: 2007
Juliette Binoche: 2001
Lizzy Gardiner: 1995
Jane Fonda: 1995
Cher: 1986
Andra Day: 2018
Kate Winslet: 1998
Leonardo DiCaprio: 1994
Susan Sarandon: 1996
Willow Bay: 2015
Martin Landau and Tim Burton: 2006
Beyoncé: 2009
Ricky Thompson: 2022
Blanca Blanco: 2015
Pharrell Williams and Helen Lasichanh: 2014
Pharrell Williams and Helen Lasichanh: 2022
Helena Bonham Carter: 1987
Amatus Sami-Karim and Mahershala Ali: 2022
Whoopi Goldberg: 1993
Some infamous looks on the most important night in Hollywood

Elegance and glamour are something that not everybody agrees on. With each year, beauty standards and fashion change, and what was chic at one time, is hideous at another. Here is a (surely controversial) list of the looks that, at the time, the media thought were a bad fashion choice.

Let's start with this wedding-inspired look worn by Geena Davis in 1992. It was designed by Ruth Meyers and Bill Hargate and the actress chose it for a special occasion: It was the night when she could have won the Oscar for her performance in 'Thelma & Louise.'

Bjork: 2001

Bjork's look in 2001 (when she was nominated for her song 'I've Seen It All') was a revolution and a fashion statement on the red carpet. Her dress shaped like a swan was designed by Marjan Pejoski and has become an iconic look. Is it maybe an icon of what you should not wear? Well, that is up for discussion!

Tom Cruise: 1989

Tom arrived at the Oscars ceremony in 1989 with a military cut and a colored and textured bow tie that wasn't appreciated by fashion experts. The actor didn't get any awards that night, but his movie, 'Rain Man,' took home four Oscars.

 

Bette Midler: 1982

This fairy-godmother-inspired dress was very much in line with Bette Midler's style but was too costumey for everyone's taste.

Randy Quaid: 1974

A bad look or just the style of that era? Maybe a mix of both. The ruffles of the shirt seemed more adequate for a high school prom than for the Oscars. But what can we do? It was the 70s…

Angelina Jolie: 2000

Before being praised by fashion critics on the red carpet, Angelina Jolie had an obscure era. Although the actress took home her first Oscar for 'Girl, Interrupted,' the media wasn't a fan of her goth look on the 2000s red carpet.

Wesley Snipes: 2022

Taking risks can sometimes give you points, but in this case, Wesley Snipes didn't have a good fashion day. Do you like this look? Maybe fashion rules for men should start changing…

Demi Moore: 1989

Creating your own outfit at the Oscars can have its consequences, and one of them is to be included in the list of worst-dressed of the night. That's what happened to Demi Moore in 1989 with this look composed of a corset, tights, skirt, and heels.

Jason Momoa: 2019

Another undefinable look: Good or bad? Some said that the colors of the suit were too informal for the occasion, but the reality is that the outfit looks really good on Jason Momoa.

Sally Kirkland: 1989

The American actress, director, and producer Sally Kirkland deserves her spot on this list. Her first fashion "fail" occurred in 1989 when she wore a kind of ice skater bodysuit on the red carpet. But it wouldn't be the last.

Sally Kirkland: 2002

In 2002, Sally Kirkland was back on the red carpet to show everyone her galactic cabaret performer gown.

Sally Kirkland: 2007

But people would get more of her style. In 2007, Kirkland wowed everyone on the red carpet with this silky cape-dress thing.

Heather Mills and Paul McCartney: 2002

Maybe Heather Mills was too bold for the occasion when she appeared on the red carpet in 2002 with a two-piece set full of transparencies, lace, and flowers. A great contrast with her partner, Paul McCartney, who, for his part, didn't put any effort into his outfit.

Uma Thurman: 2004

Uma Thurman is usually among the best dressed of the night, but she has also had some slip-ups. On the red carpet of the Oscars 2004, the actress disappointed many with this Lacroix design. Thurman later defended the dress and explained that the piece was beautiful but that she had worn it wrong.

Kim and Mick Basinger: 1990

Another actress who decided to design her own dress was Kim Basinger in 1990. It was a white satin asymmetric piece that didn't convince the fashionistas. Next to her, we can see her brother Mick wearing a red sash and a red bow tie which is the perfect look to gamble all your money in Las Vegas.

Cameron Diaz: 2002

In 2002, Cameron Diaz wanted to surprise everyone with this flowered and silk Japan-inspired design, but it didn't seem to suit her very much.

Sebastián Yatra: 2022

This very kitsch bright pink suit is maybe one of those looks that you can't stand at first, but at a second glance, you start to get into it…

 

Diablo Cody: 2007

The night that the screenwriter Diablo Cody won the statute for Best Original Screenplay for the movie 'Juno', she was also included in the list of worst dressed of the ceremony. This flowy animal print dress felt more suited for going to the beach than to Hollywood's big night.

Juliette Binoche: 2001

The 20s have been an endless source of inspiration for many designers, but in this case, Juliette Binoche's stylists went too far. The French actress's outfit looked more like a costume than an actual look.

Lizzy Gardiner: 1995

Another outfit that looked more like a Halloween costume than it should, was the one made of golden credit cards worn by Lizzy Gardiner. The look felt more suitable for a Grammy's ceremony, maybe, but not for the elegant red carpet of the Oscars.

Jane Fonda: 1995

In 1995, Jane Fonda dared to wear this eye-catching white and black dress that puzzled everyone and put the iconic actress on the worst-dressed list.

Cher: 1986

This iconic look is still bringing out the debate to the table: Is it too much, even for Cher? Some people love it, and others hate it. What do you think?

Andra Day: 2018

In 2018, Andra Day went out with everything she had and wore this extravagant pastel dress that didn't seem to amaze any fashion experts.

Kate Winslet: 1998

And here we have another Halloween costume. This time, Kate Winslet looked like she was going as Fiona from 'Shrek,' wearing a green gown in 1998.

Leonardo DiCaprio: 1994

Is this a bad look? People were actually mostly shocked about the fact that someone as young as Leonardo DiCaprio would wear something as boring and sober as this classic black suit.

Susan Sarandon: 1996

As the queen she is, Susan Sarandon appeared wearing sunglasses at the ceremony in 1996. However, they didn't complement her Dolce & Gabbana golden dress. The actress had worn better looks in other years, but at least she won the Oscar for Best Actress for her role in 'Dead Man Walking' that night.

Willow Bay: 2015

Although it seems that the dress that American presenter Willow Bay wore in 2015 was just simple 'Star Wars' merchandise, it was actually a dress designed by the brand Rodarte.

Martin Landau and Tim Burton: 2006

About Martin Landau's look we are not going to say anything (all our respects to one of the biggest Hollywood stars), but the red shirt that Tim Burton wore the night he won two awards for his movie 'Ed Wood' is a very questionable fashion move.

Beyoncé: 2009

The golden print was maybe a bit extreme and the whole dress looked more like a big China ceramic vase than a mermaid gown. The piece that Beyoncé wore in 2009 was designed by House of Dereon.

Ricky Thompson: 2022

The actor Ricky Thompson was trying to break all the fashion codes on the red carpet at the Oscars 2022, and maybe he went too far.

Blanca Blanco: 2015

The dress looked like it was actually on flames (?) Actress Blanca Blanco picked it out. And she failed…

Pharrell Williams and Helen Lasichanh: 2014

Maybe twinning on the red carpet wasn't a good idea after all… But on top of that, Pharrel Williams' short trousers were definitely too much.

Pharrell Williams and Helen Lasichanh: 2022

The musician is always trying to innovate and impress, and it (almost) never works out for him at the Oscars.

Helena Bonham Carter: 1987

We know it's hard to even recognize young Helena Bonham Carter and, yes, we know that goth is kind of her style, but this dress for the 1987 Oscars ceremony was a no.

Amatus Sami-Karim and Mahershala Ali: 2022

Amatus Sami-Karim and Mahershala Ali are good examples of why the red carpet of the 2022 Oscars won't be the one everybody wants to remember, fashion-wise.

Whoopi Goldberg: 1993

And lastly, we have… Whoopi Goldberg! In 1993, the actress surprised everyone with this 'original' outfit that looked like a gown a Disney witch could wear… Or are we being too harsh?

 

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