While some celebrities are dressed in the most beautiful gowns, others wear dresses that are a bit over the top and questionable. But the question is — what ended up being more iconic — the celebrity or the dress that they wore for the occasion? Hang on to your seats because some of these will have you wondering what some of these celebrities were thinking.
Zendaya
The 94th annual Academy Awards in 2022 saw the usually glamorous Zendaya even more glamorous. Instead of a traditional gown, The young Starlet chose a two-piece and that was simply to die for. The top was a cropped business-style white button-down, and the bottom was a flowy silver skirt that looked like a shimmering waterfall.
The design of the skirt as well as the exposed midriff both accentuate Zendaya's tall stature. All 5 feet 10 of it. We love her choice of accessories and the manicure which completed the whole look. You can never go wrong with classy and polished.
Gemma Chan
Gemma Chan looked like an absolute flower at the 2019 Oscars. Her floor-length gown was the perfect shade of pink to compliment her natural complexion and the design was eye-catching without being too revealing. The actress chose a multi-tiered dress that cascaded down from her shoulders all the way to the red carpet.
In our eyes, the main stars of this look are the petal-like neckline and the fact that this show-stopping piece has pockets. Pockets are so rare in women's attire, even more so when it comes to dresses, and even more so when it comes to red carpet looks.
Michelle Williams
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. She really is the total package when you think about it.
We absolutely love it. Michelle Williams might not have set the world alight with her performance as Marilyn Monroe but she certainly was convincing in terms of appearance. Moreover, Williams has shown her sheer diversity as an actress in recent times, starring in movies such as "Manchester by the Sea," "Venom," and "The Fabelmans."
Demi Moore
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. Thankfully, Moore has also balanced out her red carpet mishaps with some truly stunning costumes over the years. As for her acting career, it's safe to say that it waned quite a long time ago.
Salma Hayek
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 long past her 50th birthday 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. Whether she is emulating unconventional-looking historical figures like Frida Kahlo or playing god-like superheroes in movies like the "Eternals," Hayek always looks like a class above the rest.
Lupita Nyong’o
Lupita Nyong’o definitely stole the show in this baby blue Prada gown. It is gorgeous and she looks gorgeous in it. It is simple yet classy. The color of the dress just makes her glow. There’s not one bad thing to say about this look. She is killing it.
Over the last decade, Lupita Nyong'o has evolved into one of the most prolific actresses in all of Hollywood. In such a short span of time, she has starred in multiple successful franchises, including the "Star Wars" sequels, the "Black Panther" movies, and Jordan Peele's horror movie "Us." And this is just the beginning.
Charlize Theron
Charlize Theron 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.
When you compare Charlize in this photo to the images of her transformation for the main character in the movie "Monster," the change is so radical it's almost too hard to believe. Not only did Theron's appearance change so drastically for the movie, but her performance was so staggering that it won her an Oscar for Best Actress.
Octavia Spencer
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." And truth be told, she thoroughly deserved that award.
Not too long after, Spencer was in and around the awards circuit once again when she starred in the critically acclaimed film "The Shape of Water," which was directed by Guillermo del Toro. The movie went on to win Best Picture at the Academy Awards and her supporting role had a big part to play.
Faith Hill
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.
It was one thing for Hill to have sold somewhere in the region of 50 million albums globally. But when you consider the fact that she is also married to fellow country singer Tim McGraw, it feels like she has really won the jackpot in more ways than one. They well and truly are the power couple of the world of country.
Natalie Portman
This image was taken at the 2020 Annual Academy Awards but looking at Portman's choice of outfit we couldn't really tell. This design could work across different decades, different eras, and different places. We are obviously looking at a piece that was inspired by multiple things — Greco-Roman aesthetics, royal fashion, and possibly even the night sky.
This black base with the sheer golden overlay and the golden specs in the pattern makes us think of a high priestess or a druid of sorts performing a nightly ritual. We have no idea what the ritual would be for but it's simply magical.
Bjork
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 over a decade later. Although the outfit is strange, we feel that she can pull it off! She is the queen of quirkiness after all.
We think it's safe to say that Bjork is the most valuable commodity to have ever come out of Iceland. She has been an extremely important figure in the world of alternative music over the last few decades and many of her songs have been vital components of some of the most iconic movies and TV shows in recent memory.
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 similarly 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 off something like this.
Kate Winslet
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 an English Rose. The cross-shoulder is the perfect touch to such an elegant yet simple gown. And Winslet continues to tear it up, both on many red carpet events and on the big and small screens. She received plenty of praise for her role as the lead in the HBO miniseries "Mare of Easttown."
Amanda Seyfried
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 looked incredible on her. She wore it with such grace and seemingly zero effort. It's much more difficult to pull off than it looks, though.
The gold leaf detailing on the dress is to die for. Of course, Seyfried is much more than just a pretty face. She has delivered some pretty stellar performances over the course of her career and she still has more to look forward to. She received much applause for her role in the Hulu miniseries "The Dropout."
Jennifer Lopez
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.
Now in her 50s, JLo continues to pull off many incredible looks wherever she goes. And now, she gets to do it with her husband Ben Affleck. The couple have been through so much, both as individuals and together. Having been together back in the '00s, the couple have finally reconciled and tied the knot — hopefully for good this time.
Meryl Streep
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? Many will agree that Streep is probably the best actress of her generation. From her incredible performance alongside Dustin Hoffman in "Kramer vs. Kramer" to her more recent appearances in shows such as "Big Little Lies," Streep has seemingly done it all and is still going strong.
Cher
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.
Whether it be her many incredible red carpet appearances, her surprisingly good acting chops, or her iconic songs like "If I Could Turn Back Time" and "Believe," Cher is well and truly a jack of all trades. And although she is approaching her 80s, she still looks incredible.
Regina King
Regina King channeled her inner Elsa at the 2021 Academy Awards ceremony. She walked down the red carpet wearing the Beautiful floor length gown that was silvery light blue and truly made her pop. The metallic fabric and the rhinestones set along the design gave the dress and its wearer somewhat of a halo.
We especially loved the sleeves, or rather shoulder pieces in that case. They majestically framed King's neckline and beautiful face making her look like an arctic butterfly. It is a look fit for a queen indeed. Better yet — it's a look fit for King.
Uma Thurman
Uma Thurman brought business glam to the 2022 annual Academy Awards ceremony. Rather than opting for something that would make her pop like a bird of paradise, which is pretty common at such events, she decided to stick to office fashion. Though to be honest, no woman we know could wear that to just a regular day at the office.
Maybe if the top was paired with a nice pair of slacks. Thurman decided that this was a work event and therefore required work-appropriate attire. This black and white ensemble is sleek and chic and the pockets in the skirt are to die for.
Martha Plimpton
Oh boy, what a time capsule of an image this is. Coming in hot from 1989, this picture from the 61st Academy Awards features a few big names. At the Forefront we see Martha Plimpton wearing a cream-colored satin gown which beautifully accentuates her figure with a flowy, silky bottom and a Greek-inspired ruched top.
Plimpton is followed by the late great River Phoenix, and in the background, we see the "Top Gun" era Tom Cruise accompanied by his then-girlfriend and now ex-wife Mimi Rogers. Rogers is wearing a very era-appropriate polka-dot gown. The whole thing just screams 80s and we can't believe it's been that long!
Cindy Crawford
Cindy Crawford is one of the most beautiful supermodels ever to 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. And Richard Gere looked very happy with who he was standing next to. Of course, the apple doesn't fall far from the tree — Crawford's daughter, Kaia Gerber, is also gracing many red carpets these days.
Angelina Jolie
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!
Off the red carpet, Jolie has certainly been through a lot. From her breakdown in her marriage with Brad Pitt to her health problems that she seems to have overcome, Jolie really is a force of nature who seems to persevere through everything. Heck, she even became a superhero when she starred in the MCU movie "Eternals."
Tessa Thompson
Actress Tessa Thompson has made a name for herself with her involvement in projects like the HBO hit series "Westworld" and her portrayal of Valkyrie in the Marvel Cinematic Universe, namely in the Thor-centered movies. When she showed up at the 2019 Academy Awards red carpet she wowed us all with her frilly black gown.
The number had multiple tiers divided by sequined golden straps and more voluminous layers around the hips and the calves. Giving her the hourglass shape, the dress was perfectly accessorized with golden jewelry, black strappy sandals, and bronzy glow makeup.
Lupita Nyong'o
It is hard to say something that hasn't yet been said about Lupita Nyong'o. She's talented, she's intelligent, she's beautiful, and judging by this picture she obviously has great taste in fashion. For the 2022 Annual Academy Awards, Nyong'o chose to show up in a dress that made her look like one of the little figurines handed out to the winners.
The golden gown refracted light like no one's business, and the flashing cameras around definitely gave it some light to refract. Looking like an absolute jewel, the actress decided to wear her hair in dreadlocks set in a regal updo that tied the whole look together.
Cate Blanchett
While actress Cate Blanchett has definitely provided us with some great red-carpet moments, this one must be the best of them. Or at the top five at the very least. At the 2011 Oscars, Blanchett wowed anyone who looked with this ornamental powdery pink gown.
Designed by Givenchy, the floor-length dress has an empire waistline and textured applique that goes from the waistline down the hips and up the sides of the body, eventually culminating in a frame around the chest. Blanchett looked like the decorated frame of a vanity mirror found at some fancy palace in the best way possible.
Celine Dion
Fashion critics questioned Celine Dion’s white backward tuxedo outfit. Designed by John Galliano and worn to the 1999 Oscars, Celine told PEOPLE magazine back then that this bold look was one she did not regret. We aren’t too sure that this look will ever be a trend, though.
Truth be told, this was a much simpler time for the Canadian singer. She had sung the classic song "My Heart Will Go On" for "Titanic" just a few years prior and became one of the most recognizable names in all of pop music. Over the years, though, Dion has experienced loss in the passing of her husband and recent health issues.
Whoopi Goldberg
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.
Over the years, Goldberg has had a pretty diverse career, having first made splashes in the world of acting with roles in movies such as "The Color Purple" and "Sister Act." These days though, you are more likely to see her hosting the talk panel on the show "The View."
Jessica Alba
Actress Jessica Alba is one of those Hollywood celebrities who don't seem to age. This picture is the perfect evidence. It was taken in 2006. Let that sink in. We will leave the math of how many years it has been since then to you. To Alba, it seems like no time has passed at all.
This form-fitting gown that she wore to the 87th Academy Awards ceremony will probably still fit her today. Alba chose to rightfully show off her physical assets in a halter-style champagne-colored Versace dress that complemented her wonderfully toned form. It was adorned with a sheer lace overlay that hugged her curves and created a moment that people still write about even years later.
Amy Adams
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 features fluffy layers of feathery tulle that trailed behind her.
This was a very soft look for Amy Adams, and we are here for it. That year, she was nominated for best supporting actress but did not end up taking home the little golden statuette. However, her Oscar de la Renta gown and the whole look is a winner in our books.
Andra Day
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.
Gwyneth Paltrow
Years later, even Gwyn calls her 2002 Oscar gown a "glaring" fashion faux pas. This ballerina-inspired dress looks very similar to the costumes 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 whoever styled her for the event.
Julia Roberts
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.
Jane Fonda
Jane Fonda has always been a groundbreaker. This picture from the 1972 Oscars is just one example. It's not really noticeable from that angle, but Fonda chose to attend the ceremony wearing an all-black ensemble featuring a tailored suit-style top and a pair of pants. Yes, pants. At an award show in the early seventies. What a queen.
Fonda ended up taking home the Best Actress Award that night for her role in the movie "Klute." She gave everyone another memorable moment when instead of an acceptance speech she just chose to say "there's a great deal to say it and I'm not going to say it tonight. I would just like to really thank you very much."
Kirsten Dunst
At the 2022 Academy Awards, actress Kirsten Dunst showed up wearing a rosy red dress that blended with the red carpet almost too well. The textile of this frilly gown was layered and manipulated to create a wave-like texture at the bottom and a cloud-like texture around the chest.
Dunst's dress was vintage, but it was definitely not the kind of vintage you stumble upon at a random thrift store. The Hollywood star was fortunate enough to wear a vintage Christian Lacroix to the ceremony and look like a melting, deconstructed rose. This is how you win the vintage game, people.
Zoe Saldana
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.
Lady Gaga
Lady Gaga always gets away with pushing the boundaries. Of course, this time, she chose to do 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 picked. It has a very classy and timeless feel to it.
Rita Moreno
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 strapless gown.
Over fifty years later, Rita wore the same exact look to the event. Celebrities wearing the same outfit twice is not something you see every day, and that is truly amazing.
Winona Ryder
Actress Winona Ryder is not new to the game of gothics. In fact, she's probably the poster girl for that game if there ever was one. This picture from 1997 is the ultimate proof that even after her time as Lydia in "Beetlejuice" Ryder could still rock the goth style like no one's business.
So, to that year's Oscar ceremony she showed up wearing a Carl Lagerfeld gown that was just perfect for her — the tinsel, the sheer black lace, the layers, the creamy lining — it was a seamless merge of goth and glam with influences from both Victorian times and the Roaring Twenties.
Charlize Theron
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 1920s waves. We are eager to see what she wears in the future.
Angelina Jolie
Angelina Jolie is undeniably beautiful and is one incredible actress. At the beginning of Angelina’s career, she was known to give off this bad-girl vibe and her attire mirrored that. When she attended the Oscars in 2000, 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 romantically involved 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.
Amanda Seyfried
Amanda Seyfried does not need much to stand out. Genetics did most of the job for her. But when the actress wants to really make all eyes focus on her and nothing else she completes that assignment incredibly successfully. This was the case with this red number from the 2021 Academy Awards ceremony.
Seyfried showed up on the red carpet wearing a voluminous red tulle dress that made everything else pale in comparison. The design included a deep V neckline and a form-fitting silhouette and Seyfried paired it with a bold red lip and a sleek old Hollywood glamor updo.
Nicole Kidman
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.
Faye Dunaway
The coat dress that Faye Dunaway wore at the 1968 Oscars should be taught at fashion school. Actually, maybe they do teach it at fashion school, we wouldn't know, we never went to one. That doesn't change the fact that this look here is its own moment.
The petite-looking Dunaway is actually pretty tall but the way that this dress wraps around her makes her look like a little fragile doll. It was designed by Theadora Van Runkle and paired with matching loafers, a simple updo, and a purse that we would love to get a closer look at.
Diahann Carroll
Oh wow, we will probably need a second to catch our breath. It's just that watching Diahann Carroll in this dress completely took our breath away. This actress and singer took the stage to present the honorary award for achievement in choreography at the 1969 Oscars but it doesn't really matter which category she was presenting or who won.
Arriving at the event in this pearly pink number, they might as well just hand her all of those little golden figurines and call it a day. The sparkly sheer overlay that extends all the way to those cape-like sleeves makes her look like an actual fairy about to perform some magic.
Kate Hudson
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.
Kim Basinger
Did you know that Kim Basinger designed this Cinderella-inspired 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.
Penelope Cruz
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 train of feathers that just hit it out of the park.
Halle Berry
Halle Berry actually did go home with an Oscar that night, but she would have won our hearts either way. Nothing can change the fact that she looked absolutely stunning in this sheer gown. It showed off her amazing curves and overall figure.
She was a winner at the Oscars, and she will always be a winner in our book.
Hilary Swank
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!
Must be all those boxing classes. There aren’t too many people who could pull off a dress like this.
Anjelica Huston
It seems like each generation has its own kooky couple. The '90s, for example, had Johnny Depp and Winona Ryder wearing that crown. The 70s had these two — Anjelica Huston and Jack Nicholson. This image from the 1975 Oscars ceremony features Huston long before her Morticia Adams days but she is just as glamorous.
This beautiful metallic gown is giving us some major Under the Sea vibes. Not only is the material the color of a shiny pearl, but the pattern has glowing scales just like a mermaid's tail. Huston has absolutely no problem stealing the show in that number.
Daryl Hannah
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 nowadays. It reminds us of something right out of "The Princess Diaries."
Marion Cotillard
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 in her movie roles.
Cameron Diaz
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.
Neither did the scarf around the hips. She sure did improve in later years with her outfit choices.
Claire Danes
This picture of Claire Danes from the 1997 Annual Academy Awards is proof that you don't need any over-the-top embellishments like a super long train, sequined, brick-like shoulder pads, or copious amounts of bare skin for a noteworthy look.
Danes managed to look classically ethereal in her baby blue gown. The design works well with her natural complexion and body structure and the satin compliments her curves. She chose to accessorize with a bold silver necklace and complete the look with natural hair and understated makeup. Going with that color may have been the best way to make her pop against the deep burgundy carpet. It's something other starlets might do well to consider.
Uma Thurman
If we didn't have the context of this article and we didn't know that this image was taken at the 1995 Academy Awards, we would have thought that this was a picture of Uma Thurman on her wedding day. After all, aren't floor-length white gowns usually reserved for brides?
Apparently, though, it's just a super light shade of blue. The Prada gown was completed with a (truly) white chiffon wrap and classy diamond jewelry. This is definitely the look of a winner. Thurman and her dress were able to go up on stage that night and accept Thurman's award for Best Supporting Actress for the role she played in the movie "Ed Wood."
Juliette Binoche
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.
Cate Blanchett
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 seem 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.
Jennifer Lopez
In 2019, Jennifer 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 look a memorable one, not just for the Oscars, but in general.
Grace Kelly
Nothing says elegance and classic Hollywood like the adorable Grace Kelly. At the 1955 Academy Awards, Kelly wowed with a pastel green, satin gown from designer Edith Head. Of course, since the image here is black and white, you'll just have to take our word for it as far as the color goes.
Kelly 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 looks.
Lauren Hutton
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. After all, it was back at a time when people didn't know any better. If someone wore this look today, no doubt people would think twice before celebrating non-faux-fur.
Zendaya
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 has a cheeky midriff cutout only a stunner like her could rock.
Lady Gaga
Ah, a 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 with the structured waist makes Gaga look great.
Barbra Streisand
In 1969, Barbara Streisand, no doubt a trendsetter, shocked the red carpet 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.
Kasey Musgraves
Like a fancy little cupcake, country singer Casey Musgraves triumphed at the 2019 Oscars red carpet in a cotton candy 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.
Elizabeth Hurley
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.
Gwyneth Paltrow
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 when she won the Oscar for Best Actress.
This dress became an instant classic and she looks beautiful in it.
Kate Winslet
Channeling the likes of Grace Kelly from the 1955 Academy Awards (also featured on this list), 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.
Angelina Jolie
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. When your father is also a Hollywood star and talented actor in Jon Voigt, it is clear that the apple doesn't fall far from the tree. Jolie took the world by storm when she starred as Lara Croft in the "Tomb Raider" franchise and she hasn't looked back since.
Anne Hathaway
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 a few inches past the heels.
Hathaway once again proved her mastery, not just in acting and singing but also in beautifully refined red-carpet looks.
Jennifer Aniston
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 an impressive train. Aniston topped off the look by wisely keeping her hair fairly natural.
Jessica Chastain
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.
Saoirse Ronan
This is a 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.
Janelle Monae
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 Robin Hood-esque hood, not generally seen at glamorous events, but she made it work.
Audrey Hepburn
Literally the epitome of classic Hollywood glamour, Hepburn absolutely stunned at the 1975 Academy Awards red carpet in a Givenchy number.
The charming gown displayed an intricately beaded top with a peekaboo cutout in the middle and was embellished with a white bow. The beading is juxtaposed with a clean white skirt, which makes for a balanced, compelling look.
Winona Ryder
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.
Mira Sorvino
Mira Sorvino rocked the red carpet in a strapless gown by Armani, which gave a glam twist to what otherwise risked looking like 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.
Renée Zellweger
Dressed almost like an Oscar statuette 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.
Reese Witherspoon
Witherspoon's look in 2006 was a vintage home run. That night, she also took home the Best Actress for her role as June Carter in the hit film “Walk the Line,” so that's a double win.
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."
Rooney Mara
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.
Nicole Kidman
This image from the arrival of the 1997 Academy Awards is more than two decades old. While Tom Cruise's presence on the right will clue us in on just how long ago that was, Nicole Kidman's dress could be just as fashionable now as it was then.
This masterpiece of a gown was designed by John Galliano for his first Couture collection for Dior. As impressive as the dress is in this picture, one would need to see a full 360 look to fully appreciate it. Apart from the silky chartreuse material and the applique framing the torso, the dress also features a thigh-high slit and a fishnet back.
Madonna
Madonna has gone through various fashion eras. She had the early career fishnets and neons, the black-haired goth from the Frozen music video, and the cowboy queen aesthetic of the early 2000s among others. This image of Madonna and her brother Chris arriving at the 1998 Oscars feels like a fashion era of its own.
Designed by Olivier Theyskens, this dress has made quite a few headlines. The gown has an hourglass silhouette made possible using hooks cinching at the waist and a voluminous tulle bottom. Serving black glamor, the Queen of Pop accessorized her dramatic dress with a dramatic necklace and loose ginger curls.
Natalie Portman
2012 was a big year for Natalie Portman. Sure, the actress has had many famous roles in cinema over the years, but her work in the movie "Black Swan" is arguably the most memorable role she's had in the more recent years of her career.
She was recognized for this role at the 2012 academy awards ceremony. Portman, who got to take home the Best Actress Award that night, won our attention before she won the little figurine. All we needed was a single glance at this red polka dot number and we were hooked. Accessorized with diamond jewelry, this look is a winner.
Mila Kunis
Some people genuinely do have it all. Mila Kunis has a successful career, talent, and a husband in the form of Ashton Kutcher. Oh, and she also looks like that. Mila Kunis is one of those people who could walk on the red carpet wearing a duct-taped potato sack and still look amazing.
It is no surprise that we are still working on lifting our jaws off the floor after seeing her in this dress. This lacey lilac vision was designed by Elie Saab and worn by Kunis to the 2011 Oscars, where she was nominated for an award for her role in "Black Swan."
Tilda Swinton
Actress Tilda Swinton has long been known for her unique look. Not only has she been blessed with features that we don't see every day, but she has also been blessed with the sense of style to make them work for her in the best way possible.
Her look from the 81st Academy Awards ceremony is a fantastic example. She opted for a two-piece outfit comprised of a light, airy top and a silky full-length skirt with a ruffling detail that accentuated her tall and lanky form. The whole look was completed with chunky gold bracelets, bold red lipstick, and slicked-back hair. Simply classic.
Michelle Williams
Arriving at the 2012 annual Academy Awards, actress Michelle Williams absolutely crushed the red carpet in this strawberry gown. Designed by Louis Vuitton, this strapless number features a peplum style detail around the hips as well as a sweet little bow pin at the waist.
The pattern was actually made by layering and pleating the textile, which must have been pretty complex to create. The neckline, the little train, and the Beautiful diamond necklace all come together to create a classy and polished look which worked fantastically with Williams's blonde pixie cut. We love the shiny pink clutch that breaks through all of the red.
Winona Ryder
While Winona Ryder is known to many of us as the ultimate goth girl of the 90s, it doesn't mean she couldn't pull off a different look. Sure, she is in her element with projects like the movie "Heathers" or "Edward Scissorhands," but just look at her here.
This picture comes to us from the 1996 Academy Awards Ceremony, where Ryder was nominated for her role in the movie "The Crucible" alongside Daniel Day-Lewis. Here she is wearing a gown designed by Badgley Mischka that was years away from her goth aesthetic and dipped into the pool of the ethereal. The ivory color and the bejeweled pattern alongside her meticulous hairdo give us some major Great Gatsby vibes.
Audrey Hepburn
Owing to her upbringing in Europe during the time of a worldwide crisis and wartime, Audrey Hepburn had known hunger when she was little. This later resulted in her petite frame which is well demonstrated by the dress in this picture. This form-fitting number makes great use of Hepburn's tiny waist.
This 1954 image was taken when Hepburn left the Oscars not long after receiving her Best Actress Award for her role in the movie "Roman Holiday." According to newspapers at the time, Hepburn was feeling tired and exhausted and was instructed by her doctors to not overexert herself.
Elizabeth Taylor
Not one to shy away from the spotlight or from stirring up drama, Elizabeth Taylor attended the 1970 Academy Awards wearing this. While the gown in this picture can definitely speak for itself, we would like to try to speak for it nonetheless.
Taylor chose a lavender color that complimented her famously purple irises, and the low cut combined with the empire waist complemented her famous figure. She chose to accessorize it with a diamond-encrusted necklace featuring the famous Taylor-Burton Diamond as a pendant. And in case you were wondering, this diamond was purchased by Taylor and her then-husband Richard Burton and it's so famous it even has its own Wikipedia entry.
Farrah Fawcett
Famous for her portrayal of an ass-kicking angel, as well as for her bright smile and her eponymous hairstyle, Farrah Fawcett did not need much to stand out. She could have walked the red carpet wearing sneakers and the tracksuit and still all eyes would be on her and all jaws would be on the floor.
Be that as it may, it did not stop her from wearing this absolutely striking number to the 1978 Oscars. This golden gown matched her golden locks as well as the little golden statuette that she was presenting. The design was simple and chic and featured drapings that perfectly complimented its wearer.
Demi Moore
The red carpet at the Oscars is always more of a fashion show than anything else. Why else would the red carpet be so similar to a runway? The stars arriving at the scene all know it too and do their best to showcase the designer garb that they choose to wear.
Demi Moore knows that very well, as we've identified by her striking a pose in her Gianni Versace gown at the 1992 ceremony. The lilac gown with its floral bodice fit Moore beautifully, making her look like a cinched flower bouquet. Her long opera gloves were decorated with jewels and her pulled-up hairdo didn't steal any of the attention that the details around the shoulders were due.
Beyoncé
2005 was the first year Beyoncé attended the Oscars. It was kind of a big deal. She was just starting her solo career and about to dissolve Destiny's Child, she had her first couple of tries in acting ("Carmen: A Hip Hopera," and "Austin Powers in Goldmember") and she was out on the red carpet with her then-boyfriend and now-husband Jay Z.
Queen Bey was wearing a fabulous black velvet Atelier Versace gown. The Chic, minimalistic design included a small train trailing behind her and a delicately wavy, strapless neckline which paired beautifully with her big diamond chandelier earrings.
Helen Mirren
Even if Helen Mirren wasn't a Dame, we think we would have given her the title just by looking at this picture. Yes, we realize this is not how it works, but we don't care. Mirren was nominated for Best Actress in a Leading Role for her work in the movie "The Queen", and she looked just as regal walking down the red carpet in this beautiful outfit.
The ivory-colored top had a lacy sparkle that went beautifully with her natural complexion, but the bottom is the real star here, featuring thin layers of chiffon and golden leaf applique. Oh, and she won.
Sandra Bullock
Sandra Bullock's days of "Miss Congeniality" may be long gone, but she is still plenty congenial even decades after that breakthrough movie. You just can't not love her. She is just as lovable in this picture from the 2010 Oscars, when she won the Best Actress award for her role in the critically acclaimed movie "The Blind Side."
Bullock walked the red carpet in a sparkly champagne-colored gown which looked fantastic on her. The smart design had a sheer lacey top and a sequined bottom with a small train which kept a nice balance of light and heavy.
Gwyneth Paltrow
Gwyneth Paltrow looked like the very definition of statuesque while walking the red carpet at the 84th Academy Awards in 2012. Her Tom Ford gown was custom-made (no surprise there) and seems to be drawing from architectural inspirations.
The sleek white floor-length dress didn't settle for just showing off Paltrow's abs and upped the drama factor with a cape element that went around the shoulders and down the back. The actress cleverly topped her look off with a classy and simple hairdo and diamond-encrusted cuff bracelet. The whole look was simply screaming modern-day Greek goddess.
Reese Witherspoon
Hollywood sweetheart Reese Witherspoon already had an Academy Award under her belt from 2006 when she walked down the red carpet in 2015. That did not stop her from being a total showstopper on the red carpet 9 years later.
Witherspoon was nominated for the Best Actress award at the 87th Academy Awards for the role she played in the movie "Wild." She appeared at the event wearing an eggshell white dress with jet-black accents around the waist and the shoulders. The gown was designed by Tom Ford and paired with minimalistic diamond jewelry and simple hair styling that let the garment speak for itself.
Brie Larson
Years before her "Captain Marvel" days, actress Brie Larson definitely marked herself as a talent to be reckoned with. In 2016, the Academy acknowledged that too and named her Best Actress for the role she played in the drama movie "Room."
Larson also stirred up quite a drama on the red carpet with her fabulous blue Gucci gown. The beautiful number was brought in at the waist with the help of an ornate belt. Featuring a sheer, pleated overlay, the deep blue gown gave the impression of running ocean water. Stylist Christina Erlich shared that the dress took 2 months to make!
Taraji P. Henson
Actress Taraji P. Henson looks good and she knows it. Unafraid to play to her strengths, she showed up at the 2017 Academy Awards wearing a custom Alberta Ferretti nearly-black velvet gown that showed off her beautiful figure with a sweetheart neckline and off-shoulder sleeves.
The floor-length gown had a little train but also revealed a little leg with the help of a thigh-high slit. Her accessories of choice were a bold diamond necklace and ring as well as a matching purse. The inspiration for the look was vintage Hollywood glamor which is also very apparent in her choice of hairstyle.
Allison Williams
Forever Marnie from "Girls," actress Allison Williams was an absolute Snow White walking down the red carpet at the 90th annual Academy Awards. With her fair skin and dark hair, she is only seven dwarfs away from being a fairytale princess.
So, what do fairy tale princesses wear? In this case, they seem to wear Armani Privé. Williams donned a creamy couture gown with bejeweled mesh around the shoulders, beaded detailing at the top, and flowy chiffon layers at the bottom. Her film "Get Out" was nominated in four categories and took home one award for Best Original Screenplay.
Margot Robbie
Now known to most of us as the most Barbie-like human in the world, Margot Robbie had quite the acting career even before the Barbie movie came out. In 2018, the talented Aussie was nominated for Best Actress in a Leading Role for her portrayal of Tonya Harding in "I, Tonya."
She stepped out on the red carpet wearing a Chanel haut couture gown which looked fantastic though many people can't even guess the time and work that went into it. A little research tells us that the layered chiffon as well as the details around the bust and the upper arms took seven people and 550 hours of work to complete.