Academy Awards, also known as the Oscars is the biggest event of the year in the film industry. Celebrities book this day in their calendars a year ahead. And this night is not only about movies and artists, but almost equally importantly about outfits. In the history of 91 years of Oscars, we’ve seen everything – from the craziest costumes to the most wonderful masterpieces. Here is a collection of the most iconic ones.

Andra Day

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American singer Andra Day choose a spectacular gown for the 90th Annual Academy Awards. It for sure was an unforgettable night for her, not just because of the eye-catching outfit, but as a nominee for the best original song for 2017, she had the honor to perform on the stage of the Oscars.

Rihanna

Rihanna, who so many times proved her revolutionary and wild style in fashion to the world, with this outfit she just didn’t find the path. From the pink eyes and cheeks all the way to the heels the concept is a big no from our side.

Angelina Jolie

With a body and vibes Angelina has, it is probably impossible to blunder when it comes to dresses. And this pale colored elegant silk gown with its remarkable cleavage matches her style perfectly – even though her face seems to tell something else.

Katy Perry

Wooow, what can make a superstar to choose an outfit like this? Looking at this composition, there is actually not even one part of it that would be OK. The only explanation for choosing this costume can be that Katy Perry wanted to steal the show. Well, she definitely was the talk of the night in this red wonder.

Kendall Jenner

On the Forbes top-earning models list Kendall Jenner became the World’s Highest-Paid Model in 2017. She has nothing to be shy about, and she is famous for wearing showy dresses. This transparent gown she wore last year’s Academy Award leaves again little to the imagination.

Rita Moreno

Rita Moreno’s gown worn during the 2018 Academy Award has most probably the loveliest story of all time. This dress is from the year 1962, and she wore it when she won the Best Supporting Actress award for her role in West Side Story. Fifty-six years later, she chose this beautiful dress again for hitting the red carpet.

Nicole Kidman

Red carpet loves Nicole Kidman, she’s had a number of amazing outfits during the years. This Armani Privé gown is from the 90th Academy Awards, and it is definitely amongst her best ones. Her red lipstick and the cobalt blue dress are a great match.

Cameron Diaz

Cameron Diaz is known of her easy-going style, that she usually represents very well on the rep carpet, too. However, this kimono-style dress reminds us rather be a nightgown than an Oscars outfit. Not to mention that this rose color makes her face pale despite of the beautiful natural make-up.

Kim Kardashian West

Kim Kardashian West is famous for her extraordinary style, and for some fashion faux pas. However, this outfit is perfectly designed, carefully detailed, and emphasizes her curves and assets. Her ex-designer rapper husband might have a role in its success.

Sarah Jessica Parker

We’ve always loved Sarah Jessica Parker’s outfits since SANY’s first episode came out. However, in 2015, she might have taken it one step too far. We love the dress and the idea of this “crown”, but let’s be honest, it’s just too big and too red, just like a campfire on top of her pretty head.

Heidi Klum

This world-famous model knows how to pose even when her gown has one too many tulle layer. Looking at the two sides of this purple dress we cannot decide if she wanted to be a virgin princess or hot chick for the night.

Celine Dion

Celine Dion has the appearance of a queen, whatever she wears…except for this black and silver gown, with the scary black eye makeup. The silver sparkles remind us on a disco ball from the 80′, the black asymmetric top part leaves us with the feeling the threads got loose, and wait! Is it really a plaster fixing it?

Daryl Hannah

Kill Bill star Daryl Hannah wore this breathtaking gold dress with a pair of ivory, elbow length gloves at the 1988 Academy Awards. Fashion trends can come and go, but there are eternal pieces of clothes. This gown would amaze anyone even today. Pure elegance!

Cindy Crawford

This picture is probably the most famous one of Cindy Crawford and Richard Gere. Is was taken of the ex-couple on Cindy’s first Academy Awards. They look so brilliant and happy together. The harmony is reflected in their outfits, too, the supermodel was wearing a body-hugging, white Herve Leger dress which emphasized her incredible figure.

Gigi Hadid

Top model Gigi Hadid and her sister are well-known of choosing remarkable outfits, no matter which red carpet event they attend. At the latest Vanity Fair party, Gigi’s playful, still full of elegance black dress was definitely one of her best appearances, together with her carefully picked heels.

Demi Moore

Demi Moore usually picks rather conservative and modest gowns for the red carpet but this ensemble from her early years is definitely a big no from us. The cloak from the middle age couldn’t cover enough of her bicycle shorts. This outfit will go down in history as one of her worst red carpet choices.

Cher

Cher is typically a superstar who we love for her voice, and not necessarily for her fashion style. Even is she has an incredible shape, a number of times she has picked strange outfits. This is one of the most unflattering outfits of hers. The silk skirt is huge, and the mousy top looks like it’d have shredded by a dog. It is very far from being elegant.

Kate Upton

Model and actress Kate Upton is famous for her curves and assets and her dress couldn’t emphasize it more on this Vanity Fair Oscars party. Do you see the similarity to Marylin Monroe, too? She is like her unknown granddaughter in this outfit.

Juliette Binoche

The 90′ were the years of pathfinding in fashion for many of the stars. with many ups and downs. The 1997 Oscars was unforgettable for Juliette Binoche. Not just because she won the trophy, but because of what she wore. The brown velvet combined with this absurd Dracula-like collar is like something out of a B-grade horror movie. She may have walked away with the trophy but she certainly lost on the fashion front.

Kate Winslet

Kate proved in the Titanic how stunning she can be in these elegant dresses. She always looks beautiful on the red carpet, too, and this dress was one of her best choices. The simply tailored red gown with its cross shoulder adornment emphasizes her natural beauty. And most probably she feels the same, her contented smile tells it all.

Liz Hurley

Just like Cindy and Richard, Liz Hurley and Hugh Grant have their most iconic photo taken also on the red carpet. We cannot decide if this sparkling dress helped with the fame, or the hipe was rather for them being a couple. For such a pretty face and body there might have been better choices, but undoubtedly, Liz’s dress caused a stir at that Oscars.

Cate Blanchett

Cate Blanchett has a really soft and elegant inner beauty and appearance, wherever she is, whatever she wears. Red carpet events are no exceptions for this. She looked breathtaking in this Armani Prive gown with 3D floral detailing, which’s fine light blue color was a refreshing spot amongst the black crowd.

Lupita Nyong’o

Every little girl dreams about dresses like this. And Lupita Nyong’o made her dream come true wearing this baby blue Prada gown. The featherlight fabric, the floaty shape, the brilliantly designed cut, it all matched so well. She is our modern, reinvented Cinderella.

Amanda Seyfried

At the 2017 Academy Award, Amanda Seyfried just radiated. Mamma Mia star in this Alexander McQueen gown was stunning, her classic hairstyle and simple makeup just enhanced the ensemble, offering a timeless look.

Amy Adams

Choosing an Oscar De La Renta dress always promises a stunning look. American Hustle actress Amy Adams wore this breathtaking gown at the 2013 Oscars, and it really fitted her like a glove. She must have felt the same, as grace and elegance are reflecting on her face.

Zendaya

Singer and actress Zendaya is a real exotic beauty, and this gown with its extravagant color and print led her to headlines. She knows a lot about fashion, as she has her own clothing brand, and it comes together with her elegant and natural radiation.

Faith Hill

Singer Faith Hill probably couldn’t decide which color to go with, so she just decided to mix all the colors of the rainbow. The result was a dress mermaids wear in the bottom of the seas, or rather a candy stick? Hard to decide. What we know for sure is that this gown is not for an Oscars night.

Kim Basinger

The sexy Kim Basinger is not perfect either, now we know. She dressed up for the 62nd Academy Award in a Cinderella-like white dress, and she certainly chose the episode “messy Cinderella after running away from the ball”. The cut and design of the dress is horrible, and her hair just worsens her look.

Whoopi Goldberg

Whoopi Goldberg is one of the most adorable Hollywood actresses. We love her because she is funny and because of her comedic talent, but definitely not because of her fashion style. This ensemble is closer to a comedy than to an Oscar outfit, and seeing her face she probably had the same feeling.

Miranda Kerr

What a dress, and what a shape. Victoria’s Secret Model Miranda Kerr never fails to impress her fans, and in this dress certainly everybody could be satisfied with her look. Besides the remarkable cut of the gown its color is also a strike, this deep red matches with her warm brown hair perfectly.

Gwyneth Paltrow

Gwyneth Paltrow has a very unique style, she proved it many times. This baby pink princess gown is a perfect example of it.
Her hair pulled back gives a very innocent look, that matches very well with the Barbie-like dress, though the deep cleavage somehow looks strange – and empty- for us.

Kate Hudson

Kate Hudson is one of Hollywood’s loveliest actresses. Her charming, girly smile and aerial appearance are fully enhanced by this piece of art she wore at the 2013 Academy Award. Is it possible to outperform this outfit ever?

Charlize Theron

The South African beauty, Charlize Theron drew the eyes in this ivory gown. radiated on the red carpet. Her blonde hair and tanned skin perfectly complemented the dress, and this is certainly one of her very best outfits wearing on the red carpet ever.

Michelle Williams

The yellow color is a very rare choice when it comes to elegance, but Michelle Williams chose a beautiful shade of it, and this outfit will go down as one of her best. Her porcelain skin and the red lips against the yellow dress complement perfectly.

Emily Ratajkowski

Actress Emily Ratajkowski knows exactly how to turn people’s head towards her, and she does a great job with this black outfit at last year’s Vanity Fair Oscars party. Her eyes and face reflect how confident she is with her look.

Celine Dion again

Not too many stars can have the honor to get in this list twice, but Celine Dion made it. Unfortunately, again with a weird combo. It was back in 1999, but who could forget the backward tuxedo jacket and the huge pair of trousers she picked for the event. And we cannot ignore the black sunglasses on top of it. Our only question is: why?

Octavia Spencer

Actress Octavia Spencer probably felt she would get the Best Supporting Actress award for The Help in 2012 when choosing this absolutely amazing Tadashi Shoji dress. This dress follows her shapes so naturally and smoothly, it couldn’t be a better fit. She sparkled her way down the red carpet when accepted her trophy.

Farah Fawcett

This photo is not a very new one but definitely has a place on this list.
In her glamourous Stephen Burrows gown, Farrah Fawcett was the “golden girl” of the Academy Award back in 1978. Her dress inspired both fans and the clothing companies, and in the coming 10 years, we could have seen thousands of replicas in the discotheques all over the world.

Marion Cottilard

We already had a mermaid on this list, but that was a dress definitely not for the Oscars. Marion Cotillard’s choice was a Jean Paul Gaultier gown standing out on the red carpet, and how well it worked. No sparkles, no superfluous kitsch, only creative elegance. We love it.

Zoe Saldana

Zoe Saldana’s statement at the 2010 Academy Award was a real divisive outfit. This Givenchy Haute Couture with crystal embellished bodice and with a tulle ruffled skirt made her get in on the headlines, and she got positives and negatives. What we think is she looked breathtaking.

Meryl Streep

Meryl Streep has a massive experience of red carpet events and of Oscars. She usually chooses moderate dresses, and knowing her this Lanvin gown was a brave statement, but it worked perfectly. This was the year when she was awarded for The Iron Lady, and this outfit was meritorious for the trophy.

Emma Thompson

British actress Emma Thomson was not extraordinary in what she wore but rather in what she did on the rep carpet. She literally got down to the carpet after she accidentally stumbled, but it didn’t let her go down, in a moment she was happily posing again.

Halle Berry

This picture of Halle Berry is showing her in one of her most remarkable outfits. She amazed the crowd in this absolutely stunning dress. Her curves are showing off, at the same time the flower prints are hiding her in a brilliant way. The wonderful wine-colored silk skirt perfectly harmonizes with her skin.

Hilary Swank

Oh wow, what a dress. Hillary Swank wore this phenomenal blue dress at the 2000 Academy Award, the night she won the Oscar this year for her performance in Million Dollar Baby. The open back showed her tense shape, and as she walked to the stage to receive her award, every eye was stuck on her.

Angelina Jolie

Back in 2012 Angelina had an iconic statement for the Oscars. This black dress and the picture went viral after the event. Her pose in her Atelier Versace dress with her one leg showing became known worldwide as “Angie leg.”

Cher

Cher always does everything to pull out an extraordinary combo for red carpet events. When the Academy asked her back in 1986 to present the award for Best Supporting Actor, we could unquestionably expect a memorable statement. This outfit, however, overcome probably the wildest imagination of most of us.

Gwyneth Paltrow

Gwyn, again. We have to make the consequent, she and the bra are not the best friends. It was supposed to be a Ballerina inspired dress, but it rather reminds us of a pretty cowgirl from Tirol. Others see it as the Halloween gown of Black Swan. Let’s bring her young age as an excuse.

Bjork

So, this is the dress and the picture all of us have seen somewhere. And once you see, you never forget. Bjork’s swan dress has gone down to history as one of the most unforgettable ever seen on the Academy Award’s red carpet. And the question if it was pretty at all, really doesn’t matter anymore.

Lady Gaga

Lady Gaga is famous of her extravagant style. For many years she wore numbers on rep carpet events no one else would. This white jumpsuit would still be bold to many others, but for her is almost considered moderate. No doubt though, she looked glamorous and timeless in her outfit.

Julia Roberts

Julia Roberts is not just talented but one of the most beautiful actresses in the world. All to these gifts, she’s got a super elegant style, and this reflects on her statement for the 2001 Academy Awards. Her black dress with the train, her hair, the tiny earrings, and her glowing smile created a stunning look.

Jennifer Lopez

Jennifer Lopez is a real exotic beauty with feminine vibes and knows very well how to emphasize these. At the 2015 Oscars, her statement was a breathtaking Elie Saab gown, and she absolutely nailed it. The shape, the coloring, the neckline, it all just works so well.

Penelope Cruz

Back in 2007, the Spanish beauty Penelope Cruz totally amazed the Academy Award’s red carpet with this timeless statement. The combination of the magical train, he slicked back hair, complemented with minimal jewels was definitely the outfit of that night.

Jennifer Lawrence again

Jennifer Lawrence never disappoints her fans when it comes to red carpet events. Our beloved Katniss Everdeen proved it at a recent Vanity Fair Party again. She looked beautiful and hot in this simple but chic cropped black top and skirt, crowned by minimal jewelry.

Charlize – Nr 2.

Charlize Theron is also one of the few stars who could get twice on this list, and with a valid reason. She was stunning in this classic red Dior number on the red carpet at the 2016 Oscars. Appearing in the J’adore Dior fragrance advert she has maintained for years a good and close relationship with the French design house. This gown with its simple shape and its creative details definitely was one of her best choices througout the years.

Madonna

How could we leave out the iconic Madonna from the list? Probably the most memorable year for her was 1991 when she entered the red carpet of the Oscars with Michael Jackson on her arms. The Queen and the King looked very glamorous in their sparkling black and with ensembles.

Jennifer Lawrence

Even the bests fall down sometimes, and Jennifer Lawrence is getting pretty experienced at this. She seems to make her Oscars memorable with her struggles. After she stumbled in 2013 in her big, floor-length train, she wanted to go safe with this plain red number in 2014…but as you see, it all just happened again.

Salma Hayek

Salma Hayek is a real timeless beauty. The 51 years old actress had a very unusual, but a brilliant statement for the 2018 Oscars. This pleated purple Gucci gown with a diamond chain by Harry Winston hinted the impression of her being an Indian princess.

Irina Shayk

Supermodel Irina Shayk didn’t leave much to the imagination with this outfit at the 2015 Vanity Fair Oscars Party. The feedbacks were pretty controversy, but we think that if someone is in such a fantastic shape, why wouldn’t she show it to the world? And for this, the best choice was this playful, creative black ensembe.

Bella Hadid

Top model Bella Hadid has expressed her desire to try herself as an actress and she wouldn’t stop until she wins the Oscar one day. Well, these are big hopes and dreams indeed. Is she really that talented? We don’t know yet, but one thing we are sure of, she was absolutely hot on the red carpet in her daring red gown in 2016.

Angelina Jolie again

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We close this impressive list with a photo that belongs to the big Oscars moments. We remember that Angeline Jolie in the early years of her career was famous for her unusual bad girl pranks. Back in 2010, she entered the rep carpet with her brother on her arm. How nice, we thought. But as they walked along, they suddenly kissed each other passionately, and this moment was just really awkward to see, being one of her most bizarre Oscar moments.