Thankfully, there have been a handful of women that have successfully managed to do so. Since we simply love to keep you entertained, here’s our second installment of actresses and their timeless Oscar outfits!
Given this was her debut appearance at the Academy Awards after her burst-out role in “The Girl With the Dragon Tattoo”, Rooney Mara started strong.
The cream-colored Givenchy Haute Couture gown was everything we could have hoped for from the often goth-leaning actress. The mermaid cut was specifically designed for her by the famous dressmaker.
Cate Blanchett surprised on the 2011 Oscars red carpet in a unique Givenchy Haute Couture gown.
The lavender dress had interesting square shoulders and a pop of yellow applique to juxtapose the single-hued number. This one was a risk that absolutely paid off.
Witherspoon's look in 2006, when she won the best actress for her role as June Carter in the hit film, “Walk the Line”, was a vintage home run.
The Christian Dior gown was intricately beaded and offered a deep yet tasteful v-neck. The look could have been taken directly out of "Shakespeare's In Love."
Dressed almost like an Oscar herself, Renée Zellweger looks ravishing in a yellow strapless gown by Jean Dresses.
The yellow gown has a sweetheart neckline and a long drape of fabric that cascades down the middle. A perfectly done red lip completed the look.
Mira Sorvino rocked the red carpet in a strapless gown by Armani, which gave a glam twist to a prom gown.
This is a fit and flare dress with a sparkly, beaded bust. Her twisted updo topped off the look, creating one of the more memorable looks in Academy Award history.
So Winona Ryder was actually photographed multiple times at various Hollywood events in this black Armani dress and she still chose to wear it to the Academy Awards in 1990.
We gotta give her respect for that, as celebrities are expected to never be seen wearing the same thing twice. The Armani number is absolutely stunning with unique necking and clean black lines.
Literally the epitome of classic Hollywood glamour, Hepburn absolutely stunned at the 1975 Academy award red carpet in a Givenchy number.
The charming gown displayed an intricately beaded top with a peekaboo cutout in the middle and is embellished with a white bow. The beading is juxtaposed with a clean white skirt, which makes for a balanced, compelling look.
Always one to go bold with her fashion choices, Janelle Monae didn’t disappoint on the 2020 Oscars red carpet.
The Ralph Lauren gown took over 600 hours to make. It was created using hand embroidery only and was embellished with 168,000 Swarovski crystals. The most surprising component is the Robinhood-esque hood, not generally seen at glamorous events, but she made it work.
Another timeless classic that could have been worn during the early days of Hollywood, Saoirse Ronan looks impressive in a soft pink Calvin Klein dress.
The clean strapless lines of the dress are perfectly offset by the oversized bow in the back and the bride-like train. A natural makeup look pulls the entire ensemble together. Ronan looks like she's ready to take on the world.
Most definitely a nod to old Hollywood, in 2013 Jessica Chastain wore a sequined Armani Prive gown.
The dress was form-fitting and embellished with geometric beading, and a sweetheart neckline, popular with original Hollywood glamour. A red lip and a deep side part made this look absolutely timeless.
On the 2013 Academy Awards red carpet, Jennifer Aniston went bold with a red Valentino gown. The choice paid off.
The fit and flare strapless dress was quite a showstopper, with a slight satin sheen and impressive train. Aniston topped off the look keeping her hair fairly natural.
Hathaway looked timeless in this Armani Prive gown. The sequined, strapless dress was the perfect metallic mixture of gold and silver and offered a fitted silhouette that ran just long enough to cover the heels.
Hathaway once again proved her mastery, not just in acting and singing but also in beautifully refined runway looks.
Channeling the likes of the aforementioned Grace Kelly from the 1955 Academy Awards, Kate Winslet stunned at the 2007 Oscars in a mint green Valentino gown.
The one-strap satin dress was accented by an over-the-shoulder train. Winslet topped off the classic look with geometric gold studs and a clean updo.
Elizabeth Hurley donned a completely sequined Versace gown in 1995, but this look is so timeless that it could no doubt be worn in any Academy award era.
Hurley chose a thin double spaghetti strap dress and a matching clutch while keeping the rest of the accessories to a minimum, emphasizing the decadence of the gown.
Like a fancy little cupcake, country singer Casey Musgraves triumphed at the 2019 Oscars red carpet in bubblegum pink, Giambattista Valli gown.
The multi-layered dress was covered in tulle and offered a standout shoulder embellishment. The look was finished off with a slicked-back hairdo to counter the volume of the gown.
In, 1969, Barbara Streisand, no doubt a trendsetter, shocked the runway with a sequined, sheer blouse and trousers.
The look was surprising for an award show where the majority of the attendees show up in gowns. This Arnold Scaasi look was considered bold at the time, but that was a good thing, making the young starlet talk of the town.
Another Lady Gaga classic. After shocking Hollywood with her wild meat dress and some other off-the-wall looks, Gaga chose to go with a tame, sleek black Alexander McQueen gown.
The dress is the perfect combination of elegance and Avante Garde. The clean line strapless look alongside the structured waist make Gaga look great.
When does Zendaya not slay on any red carpet? We have never seen her sporting a bad red carpet look.
In 2021, she absolutely crushed at the Academy Awards in a lemon yellow Valentino dress. While yellow is not an easy color to wear, Zendaya looks great in it. The strapless gown consists of cutouts only a stunner like her could rock.
Okay, this Oscar look is absolute luxury at its finest. Lauren Hutton rocks a pastel rainbow gown by Halston.
The look is topped off with a metallic gold belt and, here’s the piece de resistance, a jaw-dropping fur coat. If someone wore this look today, no doubt they’d be on the best-dressed list.
Nothing says elegance and classic Hollywood like the adorable Grace Kelly. At the 1955 Academy Awards, Kelly wowed with a lime green, satin gown from designer Edith Head. She added classic pearls as well as a fashionable updo.
The gown was relatively form-fitting and had an exquisite train in the back. This is one of her most memorable.
In 2019, Lopez the woman who never ages, absolutely stunned us in this Tom Ford, sequined gown. The form-fitting frock is embroidered with a mirror mosaic and though it’s full coverage, Lopez still looks sexy in it.
The gown’s style is both modern and futuristic, which makes this a memorable one not just for the Oscars, but in general.
Cate Blanchett is looking absolutely stunning in this Armani Prive gown with 3D floral detailing. She has always been one of those women who just seems to get it right when it comes to dressing for the Oscars.
We think the pastel blue compliments her very well. We’re almost certain there isn’t anything she can’t pull off.
We really aren’t sure what’s going on here, but as we know, the nineties were an interesting time in the world of fashion. However, we’re having a really difficult time understanding where Juliette Binoche’s head was when she picked out this dress to wear to the 1997 Oscars. She’s looking like something straight out of a low-grade horror film and we just can’t get past it.
She may have gone home with a trophy that night, but you can be sure it wasn’t because of her Dracula-like ensemble.
Cher as we all know, is truly an icon. She is an amazing singer and that’s something you can’t take away from here. However, her outfit choices could sometimes be questionable. The outfit Cher is wearing in this photo is not very flattering on her body. It almost looks like a bed skirt that was made into a dress.
Not to mention, it looks quite baggy on her. Come on Cher, we expect more from you than this!
Celine Dion caused jaws to drop at the 2017 Met Gala. The 49-year-old singer wore this high slit Versace dress. It certainly caught the attention of others, but we aren’t sure if it was good or bad.
We also aren’t sure what’s going on with the funky and edgy up-do.
Cameron Diaz is an actress who always seems to kill it with her red carpet looks. However, this kimono type gown, comparable to something you may sleep in didn’t work for us.
She sure did improve in later years with her outfit choices.
At the 2008 Academy Awards, Marion Cotillard looks like a modern mermaid in this Jean Paul Gaultier dress. She finished her look with a Chopard diamond necklace and ring, and a Daniel Swarovski clutch.
Seeing this reminds us of how the 'La Vie en Rose' actress completely immerses herself into her movie roles.
When Daryl Hannah wore elbow length gloves with her stunning gold dress and long blonde waves at the 1988 Academy Awards, she got heads turning. She looks absolutely ravishing- a total princess.
We wonder how a look like this would go in 2019. It reminds us of something right out of the Princess Diaries
Katy Perry is a sensation, but we were definitely questioning her outfit choice for the Oscars. What was the look she was going for? We aren’t too sure. What we are sure of, however, is that she was trying to make a lasting impression for everyone who saw her, and we are certain that it worked.
Katy Perry is known to wear questionable outfits in general, so we are not too surprised. Just a little confused.
Hilary Swank won an Oscar in 2005 for her amazing performance in the movie Million Dollar Baby. She made quite the entrance with a very sexy, low open back Guy Laroche dress. We had no idea that Swank had such a sculpted back!
There aren’t too many people who could pull off a dress like this.
Halle Berry didn’t go home with an Oscar this night, but that doesn’t change the fact that she looks absolutely stunning in this sheer gown. It shows off her amazing curves and overall figure.
She may not have been a winner at the Oscars, but she’s a winner in our book.
This stunning Spanish actress made jaws drop at the 79th Academy Awards. She went with a very original red carpet look in a strapless blush-colored Atelier Versace gown. She wore her hair back tightly and paired it with some simple jewelry.
And you can’t forget about the trail of feathers that just hit it out of the park.
Did you know that Kim Basinger designed this Cinderella look-alike dress? She wore it to the 62nd Academy Awards. While there she won the Best Support Actress award for the role she played in L.A Confidential.
This debutante-like dress is definitely a little weird.
Kate Hudson shines in everything she wears. She wore this gold Versace dress fit for a princess that took 500 hours to make. She strutted it to the 2003 Oscars with a soft, wavy up-do.
She gets every aspect of a red-carpet event right.
This may be Emily Ratajkowski’s sexiest look yet. The mid-twenty-something Sports Illustrated model is on fire in this Stephen Khalil gown which features an embroidered sheer skirt and corset-style top.
She wore this number to the 2016 Vanity Fair Oscars party.
Irina Shayk is seen here wearing an Atelier Versace gown with a cutaway feature down the side and in its place is a sheer mesh catsuit. Apparently, this outfit caused a lot of controversy on the Red Carpet and we can see why.
It’s a very revealing outfit, but she pulls it off very well.
Nicole Kidman is someone who always sets the bar high with her looks. Here she looks nothing short of a queen at the 90th Academy Awards. Does it surprise you that she was on the best-dressed list? It doesn’t surprise us.
She looks incredible in her cobalt blue Armani Prive dress that was tailored to her body perfectly and going with a red lip was a perfect choice to tie everything together.
Do birds of a feather stick together? We would have to say so. Zendaya is not one to shy away from bold colors and patterns and we love it. She absolutely killed her 2017 Met Gala look.
The Dolce & Gabbana gown with scarlet trim is incredible.
Angelina Jolie is undeniably beautiful and is one incredible actress. At the beginning of Angelia’s career, she was known to give off this bad girl vibe and her attire mirrored that. When she attended the Oscars in 2010, she was arm in arm with her brother. While the two were walking down the carpet they exchanged a kiss that would make you think the pair were together if you didn’t know they were brother and sister.
Although we are all for a solid relationship between brother and sister, we can’t help but think that exchange was a little too odd.
This South African beauty always looks absolutely radiant on the red carpet. Her bronzed skin and beautiful blonde hair complemented this golden metallic Gucci gown wonderfully.
We love that she paired the dress with 1920’s waves. We are eager to see what she wears in the future.
Between Gigi and her sister Bella, we aren’t sure who turns heads more. It doesn’t matter though because these two sisters are drop-dead gorgeous. Regardless of the event, they are attending they always look naturally beautiful.
When Gigi attended the Vanity Fair party, she wore a cut-out dress that everyone seemed to love. We aren’t sure that anyone could have pulled this off but her.
Rita Moreno was the first Latina actress to win an academy award. In addition, she also had been nominated for 6 Emmy nominations and a Tony. In 1962 she won the Oscar for Best Supporting Actress for the role she played in West Side Story. To the event she wore a very classic black and gold boatneck gown.
Over fifty years later, Rita wore the same exact look to the event. Wearing the same outfit twice is not something you see every day, and that is truly amazing.
Lady Gaga always gets away with pushing the boundaries, of course, this time, she chose to no differently at the Academy Awards. She reached out to her designer friend Brandon Maxwell to design an outfit for her to wear to the awards
He made five custom dresses for the event and this white jumpsuit was the one that she pic. It has a very classy and timeless feel to it.
Kendall Jenner is one of the most well-known celebrities. She is known for her modeling and her appearances on Keeping Up with the Kardashians. She has accomplished so much over the years. She has become one of the world’s hottest top models and has even been seen on the cover of Vogue, a popular magazine. Recently she was seen on the red carpet in a gown that left very little to the imagination.
While it complimented her well, we have to wonder if she had any wardrobe malfunctions throughout the evening.
Some may argue that Zoe Saldana was a little over the top in this Givenchy Haute Couture dress that she wore to the 2010 Oscars. Others may argue that she absolutely killed it. The majestic train, sequins, and ruffles are in all the right places in our opinion.
This dress is very unique and she ended up on the 2009 best-dressed list.
Bella Hadid, one of the new Dior beauty ambassadors, caught everyone’s attention at the Cannes Film Festival. She wore an Alexandre Vauthier dress which complimented her very well.
She tends to always wear black to events, so this was a pretty big risk and she blew this look out of the water. Go Bella!
Not only is Julia Roberts incredibly talented, but she is also drop-dead gorgeous. She wore this vintage black and white Valentino dress to the awards. She looked absolutely unforgettable in it.
We definitely vote this dress as one of our favorites that we’ve seen her in.
This isn’t the first time that Gwyneth Paltrow looks like a real-life Barbie. She wore this pink Ralph Lauren gown to the 71st Academy Awards back in 1999 where she won the Oscar for Best Actress.
This dress became an instant classic and she looks beautiful in it.
Years later even Gwyn calls her 2002 Oscar gown a "glaring" fashion faux pas. This Ballerina inspired dress looks very similar to the costume you’d see in the movie Black Swan.
Everyone has their bad moments so we’re going to forgive her for this one. We do, however, sure hope she got rid of this stylist.
We aren’t sure if Andra Day turned a curtain into a dress with this outfit, but the cameras loved it. The colors are perfect on her as the pastels compliment her skin tone beautifully. Her bold makeup and voluminous ponytail were just enough to tie this ensemble together.
If you haven’t heard of Andra Day, she is a Grammy-nominated singer and her songs will blow you out of the water.
Amy Adams made quite the grand entrance at the 2013 Academy Awards with this dress. The color is a powdery blue with a beautiful design that featured fluffy layers of feathery tulle that trailed behind her.
This was a very soft look for Amy Adams, and we are here for it.
When Madonna arrived at the 63rd Academy Awards she was wearing roughly $20 million worth of Harry Winston diamonds. It looks like she was trying to channel her inner Marilyn Monroe.
Not to mention the queen of pop certainly made a statement with the King on her arm as her date.
Whoopi Goldberg is known for being a very versatile actress who kills every role she plays. While she may be very funny, we weren’t sure if this outfit was meant to be a joke.
This very bright pantsuit and bold lime-green-and-purple overcoat at the 1993 Oscars was a big no for us.
Fashion critics questioned Celine Dion’s white backwards tuxedo outfit designed by John Galliano that she wore to the 1999 Oscars.
Celine told PEOPLE magazine back then that she didn’t regret the bold look. We aren’t too sure that this look will ever be a trend.
Sarah Jessica Parker
It’s okay to be a little adventurous in the world of fashion because it’s how trends start. However, we aren’t sure about Sarah Jessica Parker’s ensemble back in 2015. The dress and headpiece are interesting to say the least.
We hope Sarah never pulled this out of the closet again after she wore it. We’re all wondering what she thinks about her outfit now when she looks back on it.
Miranda Kerr is known as one of the most famous Victoria's Secret models to ever walk the runway. She never fails to impress us with her looks and she certainly turned heads with this dress.
She attended the 2016 Vanity Fair Oscar Party wearing a custom Kaufman Franco gown, Christian Louboutin shoes and an Atelier Swarovski bag.
We love Katniss Everdeen and Jennifer even more. She wore an Alexander Wang gown with Anita Ko jewelry for the Vanity Fair party in 2016. It showed off a slight midriff and amazingly toned arms.
She paired this with a simple silver shoe which complimented the dress perfectly.
Angelina Jolie is one heck of an actress who may be mostly known for her role in Mr. & Mrs. Smith with Brad Pitt. Who would’ve thought that a woman with such a pale skin tone could pull off a white satin dress like the one she’s wearing?
We weren’t sure it was possible until we saw her rocking it.
You may expect a look like this from Megan Fox or Blake Lively but not Angelina Jolie, right? In 2012 her high-slit Atelier Versace gown went viral. She paired this dress with Salvatore Ferragamo's custom-made black velvet peep-toe pumps.
We admire her courage and bravery to wear something like this!
Cindy Crawford is one of the most beautiful supermodels to ever live. Recently she has been seen promoting a skincare line and it doesn’t look like she’s aged one bit. You may be wondering what a supermodel like Cindy would wear to her first Academy Awards? Well, if you’re Cindy, you could wear a trash bag and still look like a million bucks.
In the end Cindy opted for a bodycon Herve Leger dress to show off that amazing model figure.
Kim Kardashian West
Like Kendall Jenner, Kim Kardashian West is known for her appearances on KUWTK. She has always been someone who has worn questionable and revealing outfits to events that shows off the contour of her body.
However, Kanye who is not only a rapper but also now a designer made sure she glowed on the red carpet.
Gosh, this woman is beautiful! Kate Upton is a model and actress who is incredibly famous for her curves and assets. The dress she wore here to the Vanity Fair Oscars party leaves very little to the imagination.
With that being said, the dress compliments her body well and is very slimming to her waist. Not to mention she looks creepily close to Marilyn Monroe in this photo.
Emma Thompson strutted this form-fitting print embellished Roberto Cavalli dress to the 2013 AFI FEST. She had a hasty fall but played it off and posed as if nothing ever happened.
We applaud her for getting back up posing happily after that little mishap.
Cher has had no boundaries when it came to her Oscar looks over the years. In 1986 The Academy asked Cher to present the Best Supporting Actor award and she certainly made quite the entrance. She absolutely stole the red carpet with this showstopper.
Cher stood to be about ten feet tall with the headdress.
Meryl Streep usually dresses very modestly, but this Lanvin dress was a bold statement to make, and it totally worked. In 2012 Streep also took home the gold for The Iron Lady. We don’t ever recall a head-turning moment from Meryl, but this was the perfect time to make it happen. She paired this dress with Salvatore Ferragamo gold lizard sandals.
Wouldn’t you agree that this is the best she’s ever looked?
Leave it to JLo to just kill it at events. This dress just screams Oscars. The plunging neckline looks very flattering on her. She is wearing an Elie Saab gown creation from the fall/winter 2014 collection.
What’s even more amazing is the dress is all handmade! This is one of our favorite looks of all time.
Amanda Seyfried was discovered by a modeling agency in a town in Pennsylvania, and she has been killing the game ever since. At this Oscar event she wore an Alexander McQueen gown which looks incredible on her.
The gold leaf detailing on the dress is to die for.
Kate Winslet is, of course, well-known for her role in the Titanic film. No matter where she goes she always looks absolutely beautiful. She is one of the classiest stars we have ever seen. There is never a time you see her on the red carpet in something that isn’t flattering and classic.
She is the epitome of English Rose. The cross-shoulder is the perfect touch to such an elegant yet simple gown.
Trey Parker and Matt Stone
Trey Parker and Matt Stone are known for having a great sense of humor. If you aren’t sure who they are, but you’re familiar with the show South Park, know that they are the ones who created the show. They showed up to the 1999 Academy Awards wearing dresses, and we all know it was for the laughs. They tried to dress similar to Gwyneth Paltrow and Jennifer Lopez, who both are known for their iconic fashion choices.
We all got a kick out of this one, so we’re going to let it slide. We aren’t sure if any other duo could pull something like this off.
We aren’t sure what Bjork was thinking with this swan dress, but it definitely made a lasting impression as it is still being talked about roughly 16 years later. Although the outfit is strange, we feel that she can pull it off!
She is the queen of quirkiness after all.
Liz Hurley turned heads on this red carpet for a number of reasons. One being that the man on her arm was fellow British actor Hugh Grant. The other being her dress. We aren’t sure what all the buzz was about, but in our personal opinion, we think that Liz pulled off this dress beautifully.
Not to mention her arm candy wasn’t bad at all either.
The first thing that comes to mind when seeing this dress is a bag of skittles. We also think that Faith Hill may have already been Pro-LGBT before anyone else.
She is stunning and can pull off almost anything, but this Versace mermaid dress was definitely a fail in our opinion.
Octavia Spencer wore this beautiful Tadashi Shoji white gown to the 2012 Academy Awards. From the makeup to the jewelry, she looked absolutely stunning.
While there she accepted her Best Supporting Actress award for The Help.
Charlize definitely knows how to work a red carpet. She looks jaw-dropping every time she sets foot onto the carpet of an awards ceremony. You may recognize her from her many appearances in the J’adore Dior fragrance advertisement.
So of course, she was seen in a beautiful bold red dress from Dior with a deep-cut neckline and statement jewelry.
Lupita Nyong’o definitely stole the show in this baby blue Prada gown. It is gorgeous and she looks gorgeous in it. It’s simple yet classy. The color of the dress just makes her glow.
There’s no one bad thing to say about this look. She is killing it.
Salma Hayek is known for her part in the #metoo movement. While the 2018 Oscars may have come and gone, the memory of her outfit stays. Salma is 51 but doesn’t look a day over 28. Lucky! She wore a purple pleated Gucci gown with a diamond chain by Harry Winston.
She paired this dress with a dark purple lip which really tied the whole outfit together. She truly glowed on the red carpet.
We aren’t sure what Demi Moore was thinking when she put this outfit on. One may argue that this outfit goes down as one of the worst in fashion history. Others may argue that by looking at the people behind her, the outfit is a hit. It looks like she may have ridden a bicycle to the event based on what looks like bicycle shorts in the front.
We’re sorry Demi but we may have to send you to What Not to Wear after this.
This Vera Wang dress on Michelle Williams will go down in history as one of her best looks. The Brokeback Mountain actress wore this eccentric marigold yellow plunging V-neck with a low bun and side-swept bangs.
We absolutely love it.
Farrah Fawcett looked to die for at the Golden Globes ceremony in 1978. She wore an innovative Stephen Burrows gown which had inspired thousands of replicas for the disco scene.
This liquid gold dress will go down in history as one of the best.
Rihanna has no shame in her game when it comes to fashion. There is no water she won’t cross. We aren’t really sure what the look she was going for here, but she almost looks like a bouquet of flowers or colorful eucalyptus.
We aren’t sure if this is extremely innovative or if it’s just a big no. Either way, Rihanna can rock anything. You go, girl!