The All Time Most Unforgettable Oscar Dresses
The Oscars are not only an annual televised hit in the United States but all around the world. Celebrities plan extensively for this ground-breaking event, and while we all like to see who wins, many of us are just as interested in what’s the latest celebrity fashion trend. From the incredible flowing gowns gliding down the red carpet to the less effusive (but just as fashionable) shorter lengths from some more daring celebrities, we all want to know: what are they going to wear? And, who will be the best and worst dressed at the Oscars? This slideshow will show you some jaw-dropping, eye-ogling dresses modeled by some of the top in the industry.
Rihanna
Bad girl Ri Ri tends to win our hearts with her voice as well as her fashion, but not so much in this case. This fashion risk was one we don’t think she quite pulls off. Is it just me, or does Rhianna look like that one Valentine’s Day bouquet you wish you didn’t get? Some fashion experts think the same thing.
Rihanna
Angelina Jolie
This pale-colored dress against Angelina Jolie’s pale complexion was a fashion risk, but it was a risk worth taking. The dress compliments her figure so much that she looks stunning. While her face looks a little less impressed by her choice, we think this was a win for Angelina.
Angelina Jolie
Katy Perry
As Katy Perry tends to do, she started some controversy, and this time with her outfit choice. No matter whether you loved the look or hated it, nobody can say she didn’t make an impact with this dress. She, more than anyone else at the Oscars, had the goal to challenge our expectations of how women should dress for the Oscars. We’d say she achieved her goal.
Katy Perry
Bella Hadid
No one is better suited to wear a sexy red dress than supermodel Bella Hadid. Her body looks amazing and it’s no surprise that we’re all envious of her gorgeous looks.
Bella Hadid
Emily Ratajkowski
Emily Ratajkowski is the kind of woman who could look good in just about anything, and this dress is no exception. Talk about looking like a million bucks! Emily can pull off black better than most, and the flattering shape of this dress suits her sexy figure well.
Emily Ratajkowski
Irina Shayk
Irina Shayk was a hot topic in her revealing yet gorgeous dress. While she leaves little to the imagination, we wonder, was it too much? What do you think? No matter what, we think the dress is a winner.
Irina Shayk
Gigi Hadid
Looking for an incredibly famous top model who has perfect gene and bone structure? Look no further than Gigi Hadid, who has always turned heads. The event doesn’t matter, Gigi always looks stunning, and this eccentric evening gown is no exception.
Gigi Hadid1
Miranda Kerr
Victoria Secret Model Miranda Kerr looks as sexy as ever in this long, cut-out red dress. The skin in this look is not something out of character to display and adds to her appeal. This is a look we like and think works for her.
Miranda Kerr
Jaimie Alexander
American Actress, Jaimie Alexander definitely turned heads when she attended the primer of “Thor” in Los Angeles. Her little black dress was…revealing, to say the least. The Azzaro Couture dress included a revealing sheer panel that started at the neckline and went all the way down her midsection. Alexander still kept the look looking classy with her simple yet gorgeous makeup look.
Jaimie Alexander
Beyonce’
Here we have another absolutely stunning look for the icon, Beyonce’. The Queen was totally glammed up in this gorgeous gold sequin Ellie Saab dress when she attended the Golden Globes. Despite the fact that this dress had a plunging neckline and showed off a little bit too much skin, not only did she make a bold fashion statement but her presence left people completely speechless.
Beyonce’
Tracee Ellis Ross
Actor, Tracee Ellis Ross showed up to the Vanity Fair Oscar Party looking absolutely stunning! The Girlfriends star wore this Zuhair Murad Coutoure ruby, lock cut gown and looked fabulous. Her simple hair and makeup really complimented the look. Fans absolutely adored her radiance. There’s no doubt that this look is one of her best so far. What do you think?
Tracee Ellis Ross
Chrissy Teigen
We all love how beautiful Mrs. John Legend is and no matter what she wears she looks absolutely stunning. It was no different when she attended the Grammys in LA in this dazzling, low cut orange gown. Teigen’s dress also included some incredible shoulders that she totally rocked. She finished off her gorgeous look with a small clutch, shiny gold heels, and some very elegant diamond accessories.
Chrissy Teigen
Kylie Jenner
Miss Kylie Jenner has become a huge household name all over the world. The young model and cosmetics guru arrived at the Met Gala wearing lavender from head to toe. Kylie rocked the red carpet in her custom Versace lilac gown for the biggest night in fashion. Despite wearing an obvious purple wig and matching feathers, she perfectly pulled off one of her most stylish and glamorous looks. Some might say this wasn’t the best choice but we think she looks beautiful.
Kylie Jenner
Andra Day
This 2018 look from Andra Day caught our attention given the many colors and flowing, flowery garments. The Grammy-nominated turned heads not only with this dress but with how she laid down on the red carpet in it! She amped up the drama with her hairstyle choice. The thick ponytail combined with loose waves was accessorized with small pink flowers. We definitely think this original, girly look was worth the drama.
Andra Day
Rita Moreno
Who says you can’t wear the same thing twice to the Oscars? Just ask Rita Moreno. She first wore the elegant black and gold-embossed boatneck gown in 1962 when she won an Oscar for Best Supporting Actress for West Side Story. She showed us all that you can still look amazing and even jaw-dropping in the same dress, fifty-six years later.
Rita Moreno
Nicole Kidman
Leave it to Nicole Kidman to look like a complete diva at the 90th Academy Awards. Does she deserve a spot on the year’s best dressed list for her cobalt blue Armi Privé dress? We think so. The unique shape and perfect tailoring, along with the bold red lipstick, makes us think this is a dress that will be remembered for ages.
Nicole Kidman
Cameron Diaz
When thinking about the top of the best dressed list, Cameron Diaz always makes the cut. Although this kimono-esque night gown might not make the top 10, or even 25, it is without a doubt memorable and stands out from the crowd.
Cameron Diaz
Kim Kardashian West
Beautiful fashionista Kim Kardashian West takes fashion risks and we know it. Since marrying Kanye West, her style has matured and KKW’s style has improved. This dress is the perfect example of how she combines elegance with class. Plus, it shows off that KKW figure in all the best places.
Kim Kardashian West
Olivia Rodrigo
At the 2022 Grammy Awards, Olivia Rodrigo wore a black satin gown with striking corset details and hot-pink rhinestones that produced an optical illusion. The “Good 4 You” singer wore a Vivienne Westwood gown with matching opera-length gloves on the red carpet, where she was nominated in seven categories. She also wowed the other guests in attendance by wearing two pink choker necklaces and black platform stiletto heels.
Olivia Rodrigo
Sarah Jessica Parker
Fashion experts and admirers alike all know Sarah Jessica Parker for her adventurous and even sometimes experimental fashion sense. Her 2005 Oscars look may have taken it too far, some experts say. Without a doubt, she turned heads on the red carpet that night, for better or worse.
Sarah Jessica Parker
Heidi Klum
Heidi Klum is well versed in walking red carpets and used strutting catwalks. This purple flowing gown is girly and gorgeous, but some experts say it wasn’t the right choice for the Oscars.
Heidi Klum
Celine Dion
Celine Dion wins our hearts with her singing, but we can’t say this fashion risk and rocker-chick look had the same effect. The dark makeup and the black dress was not the best fashion choice for this red carpet event.
Celine Dion
Daryl Hannah
It was 1988 when Daryl Hannah combined this glamorous gold dress with elbow-length matching gloves. That, with her long blond waves certainly won some fashion points at the Oscars. Way to be setting trends and defying the norm, even in the 80s!
Darryl Hannah
Cindy Crawford
International supermodel Cindy Crawford could wear just about anything and look beautiful. At the Academy Awards, she chose a body-hugging dress by Herve Leger, and she looks like a winner. This white dress shows off her beautiful figure, and we think she made the right choice.
Cindy Crawford
Demi Moore
This look was a little out of character for Demi Moore. Her surprising look won some hearts and turned away others. Whether you preferred her more chic looks or jumped on board with this dress, it’s clear that she looks extremely comfortable and excited wearing this unique dress.
Demi Moore
Cher
Pop icon Cher is someone that everybody just has to love! She shows us that even the divas of the music world can sometimes wear less than flattering looks. While some critics called the look “unflattering,” we still love her wig!
Cher
Lady Gaga
Lady Gaga is one to set the stage for pushing boundaries and making a statement. She is a unique trendsetter and this outfit is one that matches her personality perfectly. Gaga’s style has evolved over the years and this jumpsuit just screams class and style true to Lady Gaga’s personality.
Lady Gaga
Juliette Binoche
The nineties were a time for fashion that sometimes we like to pretend never happened. Juliette Binoche’s 1997 Oscars look is one of those times. The brown velvet dress may not have been award winning, but Binoche walked away with the Best Supporting Actress Award during the show.
Juliette Binoche
Kate Winslet
Is it ever possible for Kate Winslet to look anything less than stunning? We think this dress suits her in both the long cut and red color, and against her pale skin and drawn back hair, her natural beauty is really accentuated. Way to go, Kate! You’re the English rose of the Oscars!
Kate Winslet
Liz Hurley
Liz Hurley sent shocks through the celebrity community in 1995 not only with this dress, but with the man standing by her side. When fellow British actor Hugh Grant came as her date, she started waves of controversy. Nobody at the time would know they would go on to become the ultimate celebrity couple.
Liz Hurley
Cate Blanchett
Count on Cate Blanchett to be that amazing celebrity who is always on point with her fashion choices, on and off the red carpet. Her Armani Prive gown along with the 3D floral detailing was a tribute to old Hollywood glamour.
Cate Blanchett
Lupita Nyong’o
Lupita Nyong’o adored an incredible custom-made Prada gown in baby blue to the 2014 awards. There’s not a single thing that doesn’t work in this dress. The floating shape, the amazing cut, and even the neckline are all perfect! We think this look is flawless and it’s undoubtedly one of our all time favorites.
Lupita
Amanda Seyfried
Amanda Seyfried took this Alexander McQueen gown and absolutely owned it. Her classic hairstyle coupled with the dress made for a complete look. This timeless, beautiful style is something think we will adore for ages.
Amanda Seyfried
Amy Adams
How do you make a look that can’t be topped? Take Amy Adams’ Oscar De La Renta dress and add a touch of elegance and style. Just looking at her dress, we think there’s no exception to this 2013 choice.
Amy Adams
Zendaya
Young Zendaya caused a bit of controversy with this dress. While some fashion critics think her risk awards her a spot on the best dressed list, others are not so certain. Where do you think this dress belongs? Is it a win or perhaps a faux pas?
Zendaya
Faith Hill
Faith Hill has mentioned in interviews that she dresses how she feels. We can only assume she felt extremely happy on this day, wearing a slew of bright summer colors. While some weren’t a fan of her look, others say the colors match her personality. Regardless of how you feel about the look, we can all agree her effusive happiness is attractive in and of itself.
Faith Hill
Kim Basinger
Kim Baginer is more amazing that we thought. She designed this dress herself and it is definitely an unforgettable look. She was able to take home Best Actress in a Supporting Role in this white Cinderella gown for her work in L.A. Confidential.
Kim Bassinger
Whoopi Golberg
We love Whoopi Goldberg for always finding a way to make us laugh, and if that was her point with this interestinng look, she absolutely achieved her goal.
Whoopi
Gwyneth Paltrow
Gwyneth Paltrow’s infamous pink dress is on the list of every Oscar list. Everything in this look from the powder pink dress to her unforgettable hair transformed her into a perfect Barbie doll. What’s there not to like about this dress?
Gwenyth Paltrow1
Kate Hudson
Kate Hudson exudes class, glamour, and style, and this looks shows off all of that. It’s not easy to look perfect on the red carpet year after year, and we definitely want to know how she does it.
Kate Hudson
Charlize Theron
We think Charlize Theron’s look was perfect, and is one of her best red carpet moments of all time. Critics argued Charlize’s skin and hair in this look didn’t fit with the similarly-colored dress. What do you think? Too much blending or perfect complements?
Charlize Theron
Michelle Williams
Michelle Williams nails this look with her red lips against the yellow dress and her porcelain skin. This look is beautiful and is among her best fashion choices of all time.
Michelle Williams
Celine, Again
It was 1999 when Celine Dion decided to wear a backwards tuxedo to a red carpet event. Her fans had mixed reviews, but we give her kudos for taking this big fashion risk.
Celine Dions 2nd Look
Octavia Spencer
Octavia Spencer looked so great in her dress, we have to wonder if her fashion sense had to do with taking home the Best Supporting Actress award that night.
Octavia Spencer
Farah Fawcett
Farrah Fawcett is a name everyone knows for her beauty and fashion sense. In 1978 she set a new fashion trend in her gold Stephen Burrows gown. Thousands of women copied the look after she wore it.
Farah Fawcett
Marion Cottilard
Marion Cotillard transformed into a shining mermaid in her Jean Paul Gaultier dress. We think this look sets her apart from the crowd and was a win for the night.
Marion Cottilard
Zoe Saldana
Zoe Saldana took a different turn on celebrity fashion with her Givenchy Haute Couture along with a crystal bodice and a tulle skirt that turned heads for fans and critics like. We have one thing to say about this outfit: stunning!
Zoe Saldana
Meryl Streep
Meryl Streep knows how to make a statement, and this time she did so in a gold Lanvin dress. She looks incredible, and the look is one that totally works!
Meryl Streep
Halle Berry
Halle Berry always turns heads from her natural beauty alone, and this sheer dress definitely made headlines! The maroon tones in the dress look amazing with her skin tone and showed off her figure in a classy yet sexy way. We think this belongs on the list of best dressed!
Halle Berry
Hilary Swank
Hilary Swank took home an Oscar in 2000 for her performance in Million Dollar Baby. The room lit up when she walked in with this royal blue gown with a cutout back.
Hilary Swank
Angelina Jolie
Angelina Jolie has gone viral plenty of times, and this 2012 dress was among one those times. Her a bare leg jutting out of her Atelier Versace dress put her in the headlines once again. Her beauty seems to be unmatched at times.
Angelinas 2nd Look
Cher, Again
Cher took this iconic dress and stole the red carpet with it. Her interesting headpiece along with the jeweled look was something to be remembered.
Chers 2nd Look
Bjork
Bjork transformed herself into a swan with this unforgettable Oscar moment. While we say kudos to Bjork for her fashion risk, the look is probably not one we’d want to see again.
Bjork
Julia Roberts
Julia Roberts is another celebrity who exudes class and a high sense of fashion. She looked incredible in this stunning black and white dress. The train completed the look.
Julia Roberts
Jennifer Lopez
Jennifer Lopez took this Eie Saab gown in 2015 and absolutely shined in it. All the details in the dress are perfect: the shape, the beautiful neckline, and even the colors. We say she looked like a real winner in this gown.
Jennifer Lopez
Penelope Cruz
Penelope Cruz always looks beautiful, and this dress is no exception. Everything from her hair the simple accessories complete her look to perfection.
Penelope Cruz
Salma Hayek
Was it really only at the last Oscars that 51 year old Salma Hayek wore a perfect Gucci dress with a Harry Winston diamond chain? She looks incredible! What will she wear next?
Salma Hayek
Jennifer Lawrence, Again
Jennifer Lawrence decided against a gown with a basic yet chic crop top and skirt. With such a simple look she looked surprisingly beautiful. Her smokey eyes and sleek hair complete the look. It seems she’s joining the ranks of the stars who can wear just about anything!
Jennifer Lawrence Again
Charlize, Again
If it wasn’t the case before, Charlize knows how to wear her colors. She shocked us all in this amazing red Dior dress.
Charlize Theron
Madonna
Madonna took a moment to revise her style to resemble Marilyn Monroe in this incredible look. It’s amazing that the queen of pop can master a new look so effortlessly!
Madonna
Whitney Houston
Whitney Houston was an artist who took risks, and she made sure to take risks on the red carpet too. Her 1994 white suit is beautiful, and totally works!
Whitney Houston
Mira Sorvino
Mira Sorvino looks like a princess in this dress and was able to take home an award for The Mighty Aphrodite in this amazing look. With a complete look, it’s no wonder that she won!
Mira Sorvino
Reese Witherspoon
Reese Witherspoon made sure she showed off a classic look in her vintage Christian Dior dress. She took home an award for Best Actress for Walk the Line in this beautiful dress.
Reese Witherspoon
Nicole Kidman
Nicole Kidman showed off a stunning Balenciaga gown in 2007. The bow draping from her neck compliments her style. The red dress color was perfect for her skin tone and hair. We’re sure her future dresses will have the same gorgeous appeal.
Nicole Kidmans 2nd Look
Marion Cotillard
Marion Cotillard turned heads in her 2008 Jean Paul Gaultier dress that had the look that it was literally made of fish scales! This dress, while certainly unique, looks perfect on her.
Marion Cotillard
Zoe Saldana
We can’t say this was Zoe Saldana’s best dress, and maybe not her worst. The 2010 Oscars for her in this Givenchy Haute Couture dress was an interesting choice. Her accessories, a crystal bodice and tulle train, made for a confusing look. Besides the dress, her hair and makeup were great choices!
Zoe Saldanas 2nd Look
Michelle Williams
Michelle Williams wore a small Louis Vuitton gown to her 2010 nomination for Best Actress for My Week With Marilyn. Her lipstick matched the dress perfectly and made for a great addition.
Michelle Williams 2nd Look
Gwyneth Paltrow
Gwyneth Paltrow wore a classy To Ford cocktail dress to the 2013 Oscars. Two thumbs up!
Gwyneth Paltrow
Jennifer Lawrence
Jennifer Lawrence took on the face of Dior in 2012, and we can now see how the brand has transformed her into a more mature, graceful, and gorgeous celebrity in this dress.
Jennifer Lawrence 2013
Jennifer Aniston
It’s not often that Jennifer Aniston wears red, but when she does, all we can say is: wow! At the 2013 OScars she looked gorgeous in this crimson Valentino Haute Couture gown. Let’s hope she gets more red in her wardrobe.
Jennifer Aniston
Kendall Jenner
Kendall Jenner starts off our tour of the Oscars with a dress that highlights her beauty and her modeling fame. As one of the world’s top models alongside Bella and Gigi Hadid, becoming a Victoria’s Secret model, and her family’s hit reality show ending it’s 14th season with ratings through the roof, it really makes you wonder, what else could a person want?
Kendall Jenner