The All Time Most Unforgettable Oscar Dresses

By Kumar BahukhandiJan 13, 2025

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This article appeared in Articlesvally and has been published here with permission.

There is no doubt people from around the world look forward to the Oscars every year. Celebrities must plan far in advance for this special event, and we patiently wait to see not only who wins awards but also to judge their fashion choices. There are always beautiful, bright gowns, over the top fashionista dresses and of course the extreme, unforgettable, fashion faux pas.

Kendall Jenner

This has been an extraordinary year for Kendall Jenner. Her stardom has taken a huge rise, as she became one of the world’s top models alongside her best buds Gigi and Bella Hadid. Her 2017 red carpet dress leaves little to the imagination. It shows off her naturally thin and fit figure, and hugs her curves in all the right places. We love it!

Kendall Jenner1

Kendall Jenner

Miranda Kerr

The Victoria’s Secret Model always looks amazing and she looks as sexy as ever in this red dress.

She proudly displays quite a bit of skin with this look, and we think there might be more skin on display than material. She leaves little to the imagination and it totally works.

Miranda Kerr

Hilary Swank

Swank won an award and on the red carpet in 2000.

She won the Oscar for Million Dollar Baby and she lit up the room in this beautiful, elegant blue dress.

Hilary Swank

Farah Fawcett

Farrah Fawcett wore a beautiful, golden Stephen Burrows gown in 1978.

This dress was certainly memorable and thousand of girls copied the dress after she wore it.

Farah Fawcett

Irina Shayk

Irina’s dress was the topic of the night for many people.

It is certainly revealing. We think she looks gorgeous!

Screenshot 5

Irina Shayk

Gigi Hadid

The super famous, top model and her sister have always turned heads. This decision is no exception.

We wish we had their genes and bone structure! No matter which event she attends, Gigi looks stunning.

Gigi Hadid

Gigi Hadid1

Charlize Theron

We also think this is one of her finest red carpet moments. Do you agree?

While some like to criticize the South African beauty’s skin and hair, we think it complements the dress perfectly.

Screenshot 7

Rihanna

Our favorite bad girl, Ri Ri is well known for taking fashion risks.

We usually are big fans of her style, but we aren’t quite sure she pulls this one off. Some fashion experts have commented she looks like an unflattering Valentine’s Day bouquet.

Screenshot 9

Rihanna

Angelina Jolie

Usually, such a pale-colored dress wouldn’t complement such a pale complexion. In this case, however, it totally works!

This dress definitely complements her figure and she looks absolutely beautiful. While her face might look less than impressed, we think she nailed it.

Screenshot 10

Angelina Jolie

Katy Perry

Katy Perry certainly started some controversy over this interesting outfit decision.

Whether you love this look or hate it, we think Katy Perry achieved her goal of making a huge impact on the red carpet and challenging our expectations of how a woman should dress for this event.

Katy Perry

Andra Day

The 2018 look of Andra Day certainly caught eyes with its array of materials and colors.

She added more drama with her hairstyle decision. The voluminous ponytail full with loose waves was gorgeously decorated with small pink flowers. We certainly think this is a totally original, girly look.

Andra Day

The Grammy-nominated singer, Andra Day, turned heads both with this dress and by lying down on the red carpet!

Sarah Jessica Parker

SJP is well known for her adventurous and experimental fashion sense.

Some have said she went one step too far with this 2015 look. She definitely turned heads with both the dress and the headgear.

Sarah Jessica Parker

Daryl Hannah

We commend her for this look, especially in the ’80s!

In 1988 when Daryl Hannah paired elbow-length gloves with this glamorous gold dress and long blonde waves, she certainly turned heads.

Darryl Hannah

Jennifer Lopez

In 2015, Jennifer shined in this Elie Saab gown.

Every detail is perfection: the neckline, the coloring, the shape, it all just works so well!

Jennifer Lopez

Jennifer Lawrence

She looks graceful and gorgeous in her gown.

Jennifer Lawrence became the face of Dior in 2012 and we can see why.

Jennifer Lawrence 2013

Miley Cyrus

All her jewelry was by Bvlgari.

Here we can see she went with a black sequined Yves Saint Laurent gown with a plunging neckline. She paired it with black sandals, chandelier earrings, a snake necklace, a thick bracelet, and multiple stacked rings.

Miley Cyrus

Miley Cyrus is known to make a statement while on the red carpet; more often than not, she opts for edgy looks that will definitely catch your eye.

Cardi B

Cardi B showed up with a vintage Thierry Mugler look straight from 1995. The dress featured dramatic ruffles with pearl details at the waist and neck.

The entire ensemble was made to resemble a pearl inside a clam but in a fashionable way. Cardi paired the dress with a matching pearl updo. In fact, this was the same piece that was worn on the runway.

Cardi B

Penelope Cruz

Penelope looks so beautiful!

We love the dress, her simple hair, and simple jewelry.

Penelope Cruz

Taylor Swift

At this year’s AMAs, Taylor Swift went for gold for her onstage outfit.

She sported a glittering gold bodysuit embellished with crystals and fringe detailing. To complete the look, she wore gold block-heel ankle boots with pointed toes and crystal-covered heels.

Taylor Swift

The singer was honored with the Artist of the Decade award and performed a medley of her greatest hits on stage.

Blac Chyna

31-year-old Blac Chyna attended the Oscars for the first time in 2020.

To complete her look, she paired the dress with coordinating Jimmy Choo heels and large matching blue earrings. She attended the event with Christopher Trujillo, the record producer, and recording engineer as his plus one.

Blac Chyna

She showed up wearing a black high-slit low-cut Dona Matoshi gown that featured embroidered shoulders to the show.

Geena Davis

This one is more of a throwback. The black and white ruffled minidress had ruffles that made it look somewhat like an elaborate costume.

Here we have Geena Davis at the 1992 Academy Awards wearing a dress designed by Ruth Meyers and Bill Hargateat. She paired it with long gloves.

Geena Davis

Melissa Rauch

The star recently announced an exciting pregnancy.

She is seen here in a breathtaking yellow dress that is rouched and cinched around the waist area, the color is beautifully bold and daring for someone with such a fair complexion.

Screenshot 4

Melissa Rauch

Often seen as an underdog on ‘The Big Bang Story’ Melissa Rauch takes the red carpet by storm, that’s for sure.

Jennifer Aniston

Jennifer Aniston doesn’t always wear red, but when she does, wow!

She looks stunning in this crimson Valentino Haute Couture gown at the 2013 Oscars.

Jennifer Aniston

Salma Hayek

We can’t believe she is 51 years old!

Just at this last Oscars, Salma Hayek wore a purple Gucci dress with a beautiful diamond Harry Winston chain.

Salma Hayek

Emily Ratajkowski

Emily Ratajkowski is a gorgeous woman and we love this dress on her.

We think she looks like a million dollars. She looks great in black and the shape of this dress is very flattering on her sexy figure.

Emily Ratajkowski

Cindy Crawford

Beautiful, supermodel Cindy Crawford would wear just about anything and look gorgeous.

For her first-ever Academy Award’s she picked a winner. This body-hugging Herve Leger dress shows off her incredible figure and we think she looks awesome.

Cindy Crawford

Heidi Klum

Heidi Klum is used to strutting her stuff on many catwalks and red carpets.

This purple gown is definitely girly, but some have said it was not an appropriate choice for this event.

Heidi Klum

Celine Dion

Celine Dion decided to take a risk and go for a rock chic glam look here.

We aren’t sure the dark makeup or the dress was her best style choice.

Celine Dion

Cameron Diaz

Cameron Diaz is used to being at the top of the best-dressed list.

While this kimono-esque nightgown might not be everyone’s favorite look, it is certainly bold and memorable.

Cameron Diaz

Kim Kardashian West

Fashionista KKW is known for taken fashion risks and being on top of trends in the design world. This dress is a great example.

Since her marriage to Kanye West, we think her style has matured and improved. We think this dress is elegant and classy, and it hugs her figure in all the right places.

Kim Kardashian West

Demi Moore

Demi Moore really surprised us with this look. She usually dresses way more chic.

Wither you love this dress or not, it is undeniable that she looks extremely happy wearing this interesting dress.

Demi Moore

Cher

We absolutely love Cher! Some style critics called this look “unflattering.

She is absolutely an icon but even total divas can wear not the most flattering looks.” We aren’t sure about the dress, but we dig the wig!

Cher

Lady Gaga

Lady Gaga always is always pushing the boundaries and is an amazing fashion trend setter.

This outfit certainly fits the bill. Lady Gaga’s style has certainly evolved and this jump suit exudes class and timeless style.

Lady Gaga

Juliette Binoche

The nineties were an interesting time for fashion. This one is not easy to forget.

Juliette Binoche’s 1997 Oscars look was this dress made from brown velvet. Some might not give the dress an award, but she walked with the Best Supporting Actress Award during this show.

Juliette Binoche

Kate Winslet

Kate Winslet always looks stunning on and off the red carpet. We totally think this dress suits her with both the cut and the color.

Against her pale skin this dress really accentuates her natural beauty. Nice choice, Kate! You look like the epitome of a beautiful English rose!

Kate Winslet

Liz Hurley

Liz Hurley started a wave of controversy in 1995 not only due to this dress, but also the man on her arm.

Her date this year was fellow British actor, Huge Grant. They later went on to become the ultimate Hollywood couple.

Liz Hurley

Cate Blanchett

This Armani Prive gown complete with the 3D floral detailing was a well down ode to old Hollywood glamor.

Cate Blanchett is one amazing woman who seems to always get it right with her fashion choices during awards seasons.

Cate Blanchett

Lupita Nyong’o

Lupita Nyong’o wore this amazing custom baby blue prada gown to the 2014 awards. Everything about this dress works on her.

The floating shape, cut, neckline, everything! We think there is not one flaw in this look and it is one of our all time favorite celebrity dresses.

Lupita

Amanda Seyfried

Amanda Seyfried really owned this Alexander McQueen gown.

We think she made a great decision with both the dress and her classic hairstyle. It offers a beautiful, timeless look that we just adore.

Amanda Seyfried

Amy Adams

We love Amy Adams’ style and this Oscar De La Renta dress is no exception. Well done, Amy!

The American Hustle actress looked like the epitome of elegance at the 2013 awards. We aren’t sure she can top this look.

Amy Adams

Zendaya

This young beauty stirred up a wave of controversy with this dress.

Some fashion critics think this risk deserves a place on the best dressed list, while others strongly disagree. Do you think this is a fashion win or a huge faux pas?

Zendaya

Faith Hill

Faith has said in many interviews she likes to dress how she feels.

She must have felt very happy on this day because she chose to wear the happiest summer colors. While some people aren’t a huge fan of this look, we think she looks jovial and that is very attractive on its own.

Faith Hill

Kim Basinger

Kim Baginer designed this dress herself and it definitely is an unforgettable look.A. Confidential.

She rocked this white Cinderella look during the 62nd Academy Awards where she won Best Actress in a Supporting Role for her work in L.

Kim Bassinger

Whoopi Golberg

We love this comedic actress to death, and if her goal was to put a smile on our face with this look she definitely achieved that.

Whoopi

Gwyneth Paltrow

There is no Oscar Dress list without Gwen’s infamous pink dress. This look is definitely unforgettable.

We love everything about this look from the dress to the hair. She looks like a perfect real life Barbie doll.

Gwenyth Paltrow1

Kate Hudson

Kate Hudson definitely has a classy, glamour style, and this look reflects that.

She has perfected the art of looking amazing on the red carpet and we wonder every year how she will look.

Kate Hudson

Michelle Williams

Michelle Williams is beautiful and this dress is definitely one of her best fashion decisions ever.

She nails it with the red lips against the yellow dress and her porcelain skin. Everything about this look is red carpet perfection.

Michelle Williams

Celine, Again

Back in 1999, Celine Dion wore a backwards tuxedo.

There were mixed opinions about this look, but we think it is awesome whenever a celebrity takes a risk!

Celine Dions 2nd Look

Octavia Spencer

Octavia Spencer looked amazing in this dress.

That night she won the award for Best Supporting Actress.

Octavia Spencer

Marion Cottilard

Marion Cotillard shined in a beautiful, mermaid like Jean Paul Gaultier dress.

Marion Cottilard

Zoe Saldana

Simply beautiful!

In 2010, Zoe Saldana wore a Givenchy Haute Couture with crystal embellished bodice and a tulle ruffled skirt that made heads turn.

Zoe Saldana

Meryl Streep

It absolutely works and she looks great!

Meryl Streep made a statement in this gold Lanvin dress.

Meryl Streep

Halle Berry

This dress definitiely made headlines! Halle looked beautiful in this sheer dress.

The maroon looks beautiful against her skin and it shows off her figure in a very classy way. This dress is a winner in our book!

Halle Berry

Angelina Jolie

In 2012 Angelina wore an Atelier Versace dress.

Her pose showing off one leg went viral because she looked so beautiful!

Angelinas 2nd Look

Cher, Again

This dress is definitely iconic.

Cher stole the red carpet in this wild headpiece and black jewel-encrusted look.

Chers 2nd Look

Bjork

This swan dress is definitely an unforgettable Oscar moment.

We commend Bjork for taking a risk, but this might not be her best look.

Bjork

Julia Roberts

We love the train in the back.

Julia Roberts looked stunning and classic in this dress.

Julia Roberts

Bella Hadid

Her body looks amazing in this sexy red dress.

No wonder Bella is one of the top models in the world!

Bella Hadid

Jennifer Lawrence, Again

We love her smoky eyes and sleek haircut. Everything goes so well together!

Jennifer Lawrence rocked a simple but chic cropped top and skirt, and she looked beautiful.

Jennifer Lawrence Again

Charlize, Again

Charlize knows how to wear color.

She wowed in this red Dior dress.

Charlize Theron

Madonna

We think she looks stunning!

The queen of pop resembled Marilyn Monroe in this beautiful look.

Madonna

Whitney Houston

We love it and think it definitely works!

Whitney Houston definitely took a risk wearing this modern white suit back in 1994.

Whitney Houston

Mira Sorvino

Mira Sorvino won on and off the red carpet!

She looks like a princess and also won the award for The Mighty Aphrodite.

Mira Sorvino

Reese Witherspoon

Reese looks classic in this vintage Christain Dior dress.

She won the award for best actress for Walk the Line that evening.

Reese Witherspoon

Rita Moreno

We totally love this decision and this look. She looks amazing!

Rita Moreno wore it for the first time in 1962 when she won the Oscar for Best Supporting Actress for her role in West Side Story. Fifty-six years later, she decided to rock the same look complete with beautiful black satin opera length gloves.

Rita Moreno

This is the second time this elegant black and gold boatneck gown has hit the red carpet.

Nicole Kidman

At the 90th Academy Awards, Nicole Kidman looks like a total red carpet diva. The shape is so unique and it is tailored to perfection.

We think she deserves a place on the year’s best dress list for her cobalt blue Armi Privé dress. We also love the bold red lipstick she chose to complement this look.

Nicole Kidman

And again, Nicole Kidman wore this Balenciaga gown back in 2007. We love the bow draping from her neck.

We think this dress really compliments her figure and the color is perfect for her skin and hair color. Nice job, Nicole!

Nicole Kidmans 2nd Look

Marion Cotillard

Marion Cotillard is just beautiful! We think it is different and looks perfect on her!

In 2008 she turned heads wearing this Jean Paul Gaultier dress that looked as though it was literally made of fish scales.

Marion Cotillard

Zoe Saldana

Zoe Saldana at the 2010 Oscars was, well, interesting.

She chose this Givenchy Haute Couture dress with a crystal embellished bodice and a big tulle train. We aren’t sure it is her best dress, but her makeup, hair, and accessories are great!

Zoe Saldanas 2nd Look

Michelle Williams

Back in 2010, Michelle Williams was nominated for Best Actress for My Week With Marilyn.

She wore this cute red tulle Louis Vuitton gown. The matching lipstick is a beautiful touch.

Michelle Williams 2nd Look

Gwyneth Paltrow

Gwen wore this to the 2012 Awards.

It is a beautiful Tom Ford cocktail dress. We approve!

Gwyneth Paltrow

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The All Time Most Unforgettable Oscar Dresses

Kendall Jenner

Miranda Kerr

Hilary Swank

Farah Fawcett

Irina Shayk

Gigi Hadid

Charlize Theron

Rihanna

Angelina Jolie

Katy Perry

Andra Day

Sarah Jessica Parker

Daryl Hannah

Jennifer Lopez

Jennifer Lawrence

Miley Cyrus

Cardi B

Penelope Cruz

Taylor Swift

Blac Chyna

Geena Davis

Melissa Rauch

Jennifer Aniston

Salma Hayek

Emily Ratajkowski

Cindy Crawford

Heidi Klum

Celine Dion

Cameron Diaz

Kim Kardashian West

Demi Moore

Cher

Lady Gaga

Juliette Binoche

Kate Winslet

Liz Hurley

Cate Blanchett

Lupita Nyong’o

Amanda Seyfried

Amy Adams

Zendaya

Faith Hill

Kim Basinger

Whoopi Golberg

Gwyneth Paltrow

Kate Hudson

Michelle Williams

Celine, Again

Octavia Spencer

Marion Cottilard

Zoe Saldana

Meryl Streep

Halle Berry

Angelina Jolie

Cher, Again

Bjork

Julia Roberts

Bella Hadid

Jennifer Lawrence, Again

Charlize, Again

Madonna

Whitney Houston

Mira Sorvino

Reese Witherspoon

Rita Moreno

Nicole Kidman

Nicole Kidman

Marion Cotillard

Zoe Saldana

Michelle Williams

Gwyneth Paltrow

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