Luckily for you, we’ve racked up even more stars who took their style to new heights. These looks are so out there that they’ll have you wondering who and why designed these outfits. So, without further ado, prepare your eyes.
Would You Like Fries With That?
The Met has become so huge in recent years that celebs sport different looks in the main event and in the after-party. If you thought the after-party outfits would be a little bit more chill, think again.
Katy Perry takes parties very seriously, so in 2019 she wore a full-on hamburger costume for the one that came after the main event. Perry always slays it when it comes to the Gala, and we gotta admit we love this quirky look.
A Cinderella Moment
Zendaya smashed 2019's theme. What's campier than an over-the-top Disney-inspired princess gown? Nothing! The dress was designed by legendary Tommy Hilfiger.
The actress's stylist, Roach, accompanied her on the red carpet dressed as the fairy godmother. She also had a bag shaped like Cinderella's pumpkin carriage, and if that's not enough, her gown lit up on the red carpet. This look gets ten out of ten.
The Wrong Party
As we already mentioned, after-parties got big in recent years. Kim Kardashian wasn't about to let anyone outshine her. While this look can't be ignored, we are not sure it's a good thing. Maybe she thought it was Halloween?
In a skintight blue dress and a shiny wig, Kim is obviously giving a nod to Cher. While she did go all out, we are not fans of the look.
A Train to Remember
A trial will always steal the show. Endless trains have been a recurring theme in this prestigious ball, and for a good reason. They have an impact that can't be denied.
For Cardi B, there's no such thing as overdoing it. A sparkly cap? Sure. Feathers Galore? No problem. A 10 feet train? Bring it on! This $250,000 dress was worth every penny.
Floral Gown
In 2013, model Karlie Kloss wore a Louis Vuitton dress, but her Monique Pean necklace almost stole the show. Her bright pink lips look fabulous, though we are not sold on the hair and overall styling.
While we love all of the elements of her outfit, we are not sure they all fit together to make a cohesive look.
A Bright Beret
Back in 2003, the Met Gala wasn't as prominent as it is today, which is the only explanation as to why Dunst showed up in this look. We do get that beret was trendy back in the early noughties, but the bright hat just doesn't go with Kirsten's black dress at all.
Luckily for Dunst, she's had many years to make up for this look, and most people have probably forgotten it by now.
Feathered Up
"The Lord of the Rings: The Fellowship of the Ring," star Liv Tyler showed up to the 2011 Met Gala in a white and yellow Givenchy gown.
Don't get us wrong, we do think the dress is gorgeous, but it does feel like it could have worked for any red carpet. It just doesn't have that "WOW" factor we were looking for.
A Beautiful Monster
Musician Janelle Monae presented this wonderfully whimsical dress at the 2019 Met Gala. She cooperated with Christian Siriano to create this gown, which Monae says was inspired by science fiction as well as the duality of the feminine and masculine.
Whatever she was inspired by, it worked; this dress is to die for. It is a unique piece that could have only been worn at the Met Gala.
All Eyes on Ezra
"Fantastic Beasts" star Ezra Miller came up with an outfit we couldn't keep our eyes off of. As if his Burberry suit, rhinestone corset, and shoes weren't enough, he also had a mask of his own face.
But that wasn't even the creepy part; behind the mask, he hid an array of eyes. Miller was inspired by artists like Dali and Magritte, and he does look like a work of art in this outfit.
Emma's Armor
We won't blame you if you forgot, but Emma Stone was a brunette for a short while. Don't worry; she dyed her hair back to her iconic red. For the Met Gala, The "La La Land" actress went for an armored white dress, which did fit with the night's theme of "Fashion in an Age of Technology."
This look wasn't our favorite look of the night, but we are still huge fans of Stone.
Full Metal Dress
Swift is known as a master songwriter, and her style tends to change to embody the mood of her latest album. In 2016, she had not yet released her album "Reputation," but she already knew it would be filled with snake imagery.
This could be the reason why she chose to wear this snake-scaled metallic dress by Louis Vuitton. Taylor bleached her hair, especially for the event. Social media wasn't a fan of the look, which was edgier than most of Taylor's looks.
Big Bird
We have to admit that we expect a lot from the woman known as "Vogue's" editor-in-chief. While the Met's theme changes every year, Anna Wintour usually chooses to go with something classic.
Her cape makes her look like a high-fashion bird. She always wears a Chanel couture dress, and her hair is always in a bob. But at least in 2019, she gave us a little more, which makes sense with a theme like "Camp."
Put a Bow On It
This Prada frock might seem strange at first, but when the theme is camp, there's no such thing as too much. "The Great Gatsby" actor enrobed an elegant evening gown made out of various fabrics and textures.
With red sequins and black stain, the pink sash was really needed in order to somehow tie the whole look together, and Carey Mulligan looks great in it.
Double Trouble
Do you guys remember back when the Olsen Twins used to be everywhere? In 2005, the two made their first appearance at the Met Gala.
The Olsens didn't get the memo about the night's theme. While the Gala was celebrating Chanel, Ashley wore Oscar de la Renta while Mary-Kate donned a vintage piece. Despite these looks being so bluntly of the early noughties, we still enjoy them.
Eyebrow Game
Kristen Stewart ascended to fame when she portrayed Bella Swan in the "Twilight Saga" movies. Her 2019 Gala look was all about the hair and make-up.
Her Chanel outfit is monochromatic, letting her hair orange hair and eyebrows shine. Kristen mentioned she was inspired by David Bowie, and it shows. We love how edgy this look is.
Little Black Dress
Kylie Jenner, "Forbes's" youngest self-made billionaire, was dressed to the nines in 2019's Met Gala. In a long gown designed by Alexander Wang and bejeweled sunnies, she looks like she's ready to take on the world, though, let's admit it, she already has.
This look is tame compared to what we're used to seeing at the Metropolitan Museum Gala, but it still works.
Ombré
As one of the world's highest-paid actresses, Scarlett didn't have to save money on a Met Gala dress. In 2018, she decided to spoil herself with a Marchesa ombré gown.
This off-shoulder look isn't our favorite, but we trust Johansson's judgment. As one of Hollywood's leading ladies, she knows what she's doing!
Viva Liberace
This gorgeous garment was designed by "Project Runway" season four winner Christian Siriano. The sparkly orange tuxedo and the magnificent cape both took two months to make.
"American Horror Story" and "Glee" creator Ryan Murphy reported the garment celebrated child prodigy Liberace. The outfit weighs over 100 lbs, but no pain, no gain, right? This look is a winner!
Liquid Gold
This dress is gold! It literally looks like Hathaway is wearing liquid gold. The cape-like dress was custom-designed for Anne by no other than Ralph Lauren.
The story behind the dress is just as exciting. Apparently, the gown was inspired by Buddha. The actress knocked 2015's (China: Through the Looking Glass) theme out of the park.
Pretty in Pink
"Scandal"'s Kerry Washington adorned a Prada gown at the 2015 Met Gala. In a pink princess dress with embroidery on its train, the actress looked flawless. The voluminous frock was just the best choice to impress everyone at the Gala.
The dress featured a low back and a bow. Kerry's smokey eye sealed the deal and made this look unforgettable.
Red & Blue
This dress is pretty and would work great for a red carpet or a movie premiere, but not for the Met Gala. Don't get us wrong, Jessica Chastain looks divine in this Prada gown.
You can't really go wrong with blue silk, right? The dress is beautifully constructed, and Jessica's makeup and hair are also spot-on; we just think she could have done more.
Shoulder Hair
When the theme is "Camp," and the attendee is RuPaul, the campiest drag queen out there, we'd expect to be blown away.
We do applaud the "Drag Race" host and producer for not taking the easy way out and showing up in an enormous dress. On the other hand, his striped sequin suit just wasn't enough.
A Hot Mess
In 2017's Gala, Jake Gyllenhaal's sister, actress Maggie, donned a sequinned ensemble in green and purple. We think the dress has a floral theme to it, but honestly, it is so shiny it's hard to tell.
While the garment may appear to be a dress, it is actually a wide pant. This look is our definition of a hot mess!
The Corporate Look
Karli Kloss's job, as a model, is to take pictures wearing elaborate garments. Maybe this is why she chose such a simple look for the Met. The dress is inspired by something one would wear to the office, only, you know, not actually.
This take on office attire is a bit too revealing to be worn in a business meeting. Either way, while this is a nice look, we were underwhelmed by both the dress and the hair and makeup.
The Wrong Color
This look scored Selena a shameful place in many of the year's worst-dressed list. Not only was it considered a failure, but it has also sparked some controversy.
Many complained that her tan and makeup made her look as if she's from a different ethnicity. While the dress is not great, it isn't as bad as the hair and makeup. Selena is a natural beauty, and we're sure her next Met Gala look is going to be spectacular.
A Cross Across
When it came time to dress for 2018's Met Gala, saint J.Lo knew exactly what to do. She went for a literal interpretation of the theme, wearing a giant cross across her chest.
The bejeweled Balmain dress was made especially for her by Olivier Rousteing. The gown was inspired by an '88 "Vogue" cover, and it took over a month to make! It was definitely worth it, this one.
Marked With a White Dress
Halsey wore white from head to toe in a garment inspired by 80's cult classic "Blade runner. " The dress was designed with the movie's female lead in mind and was tailored out of old jackets and dresses.
With cotton satin and stretch silk, Halsey looks classy and edgy at the same time. She has DKNY designers to thank for this successful design.
God is a Woman
Rihana is the kind of woman who knows how to pull off a look, no matter how insane it is. In this case, the dress and the hat look like they weigh more than the Barbadian singer herself.
But the seasoned performer totally nailed 2018's theme, Catholic Imagination. Her dress makes her look like an opulent, godly pope. Work it, girl!
Teal Lilies
The 2019 Met Gala was one of the best ones yet, simply because its theme, "Camp: Notes on Fashion," allowed for some of the craziest outfits we have ever seen. "Riverdale" star Lili Reinhart attended the ball with her then-boyfriend, Cole Sprouse.
We are undecided about this dress; while the color suits Lili and her hair and makeup are gorgeous, something about the proportions of this dress is a little bit off. But, she still manages to look spectacular in it, somehow.
Not Patriotic Enough
With a theme like "American Woman: Fashioning a National Identity," we would have expected to see something a little bit more patriotic. While January Jones's eyeshadow is blue, and her hair is red (well, orange), we can't really see how her dress fits the theme.
She always looks stunning, but this purple Yves Saint Laurent dress didn't really leave an impression on us. It was quite forgettable.
Trailing Behind
Karolina Kurkova showed up to the 2005 Gala in this long white gown, which included a large, “I love you,” sewn across in bright red. Other images from the night reveal the dirty, wet steps outside of the museum, so who knows what the bottom of the dress looked like by the end of the evening!
While she may have been trying to nod to the House of Chanel, who was being honored with that year’s theme, it was more of a swing and a miss than a home run.
3L-What Were They Thinking?
The members of the girl’s group 3LW confused everyone a little bit when they showed up to the 2001 Met Gala in neon, skin-tight, and short attire. And do you blame them? No one’s entirely sure what those outfits have to do with the theme of "Jacqueline Kennedy: The White House Years."
Do you care to wager a guess? Well, they turned heads alright, but probably not in the way they’d hoped.
Dressing in the Dark
Designer John Galliano appeared at the 2006 Gala looking like he’d be up drinking the night before with a group of pirates who went crazy with a Bedazzler, passed out for a few minutes, and been woken up and told he had to hit the carpet.
His date, Charlize Theron, opted for a flowy, deep-red Christian Dior dress, which looks nice but pretty mismatched with her date's attire. Though, that seems to be on him.
Kilting It
Alan Cumming made Vogue’s best-dressed men at the Met Gala list in 2001 when he appeared at the "Jacqueline Kennedy: The White House Years"-themed event in his tartan kilt.
This isn’t the first (or last) time the Scottish-American actor and comedian has arrived at events in kilts. Still, the pose he was snapped in here seems a bit questionable.
Walking Saucer
When Solange Knowles arrived at the 2015 Met Gala, she stopped many people in their tracks – but many were probably just trying to figure out what exactly it was they were looking at her wearing.
The Giles dress has an odd shape that makes her look like some kind of vehicle you’d see on "Star Trek" or "The Orville." But hey, if ever there were a time to dress like a flying saucer, it’d be at the Met Gala, right?
Give us a Twirl
Zendaya nailed her look for the 2015 Gala, which had the theme of "China: Through the Looking Glass." She looked gorgeous in an interesting and embellished Fausto Puglisi dress, which featured sun designs against the skirt, along with a simple pair of black stilettos.
Her long hair topped with a matching crown-like headband was the icing on the cake. Jessica Alba could take a few notes from Zendaya about how to pick an outfit to walk the stairs at the Metropolitan Museum of Art!
Altar Man
Well, you can’t say that Chadwick Boseman didn’t adhere to the whole "Catholic Imagination" aspect of that year’s theme when he arrived at the 2018 Gala dressed like, well, like this.
The custom Versace tux and a cape are covered in symbolism and definitely stand out against the crowd. The Met Gala has been called the “Oscars of Fashion,” so one must really dress for the occasion, we suppose.
Insta-Classic
2014 may have been rough for several celebrities in terrible outfits, but Blake Lively was not one of them. Her custom, form-fitting Gucci gown looks gorgeous, from the color and details to the way it drapes and flows. She chose to accentuate the look with classic old Hollywood pin curls.
Her husband, Ryan Reynolds, has described her getting ready for the Galas as “an athletic event.” “I’m not even sure how shoes got in the freezer; there’s Kung Fu involved, it’s really intense,” he jokingly told "Glamour" magazine. Whatever she’s doing, it's working!
Stiff Catwalk
Shailene Woodley’s 2018 Gala getup seems as though it’d be really tough to walk – and sit down – in. But she must’ve thought the Ralph Lauren design worked well with the "Heavenly Bodies" theme.
In fact, two other celebrities showed up in outfits that looked very similar and nodded to Joan of Arc. Unfortunately, hers earned her a spot on several worst-dressed lists for that year’s event.
Avant-Garde
What was going on with the whole puffed-up look at the 2017 Met Gala, with the theme "Rei Kawakubo/Comme des Garcons: Art of the In-Between"? Solange Knowles chose this extra-long puffer coat, with a dress-like train behind, over puffy pants, and a white button-down.
Granted, the theme was avant-garde, so she adhered. But she’s also been compared to a sleeping bag in the interesting getup. Hey, at least she looks comfortable, which is more than can be said about nine out of ten looks on the list!
From Top to…Feathers?
Beyonce’s Givenchy couture gown looks beautiful on her – from the shoulders to the thighs, anyway. The purple feathers just destroy the outfit which she chose for the 2012 Gala in New York.
The dress got mixed reviews, with many not only disliking the feathers but also claiming that it was too sheer in some areas. Her sleeked-back ponytail and classic makeup look nice – and perhaps the dress would’ve too, sans the feathers. Especially purple feathers! Yikes!
Side Show
Stars take some calculated risks when they choose certain designs to wear out to events. A sheer dress, or Gwyneth Paltrow’s slinky purple Prada mini dress, may make for some embarrassing moments on the red carpet – depending on how you feel about flashing the world.
Still, the dress itself, while fairly simple, looks stunning on her, even if parts of her are pretty exposed.
Glow Getter
As if Katy Perry doesn’t garner enough attention on the red carpet, she wears a spotlight dress at the 2010 event. The dress, which on its own was fairly simple, done in pale pink with one shoulder, was lined with rope lights that glowed in different colors.
Again, the getup received mixed reviews, with many saying they liked the dress, but the large necklace she chose to accessorize with was overkill. What do you think?
Golden Goddess
Nicole Kidman was stunned in this nude-colored, form-fitting embellished dress by Tom Ford for Gucci at the 2003 Gala. The event was governed by the theme, "Goddess: The Classical Mode," so the gown was a perfect choice for the evening.
Her sleek ponytail, a simple clutch, and drapey earrings add nice touches to the ensemble as well.
Condiment Gown
At the 2014 Met Gala, actress Katie Holmes arrived in a super-bright, mustard-colored yellow dress by Marchesa. Perhaps she was trying to channel Belle from "Beauty and the Beast."
However, something just got lost in translation, and the off-colored, off-the-shoulder dress scored her a spot on several worst-dressed lists that year. In fact, that year’s event has been called the “worst-dressed met Gala ever.”
Curtain Call
Kim Kardashian’s 2013 Met Gala getup is reminiscent of curtains you’d see hanging in grandma and grandpa’s place.
The pregnant celebrity chose this busy, floral print, which didn’t suit her very well, and drew an array of negative reviews from commentators after the event. Later, she admitted that she “cried the whole way home” over the poor response to the Givenchy gown.
Back to the Future
You know, Woodley’s look also seems like it may have fit in better at the 2016 Gala, with its Star Trek-like feel. Katy Perry arrived in this fitted, black, and gold Prada gown. The dress is pretty lovely, but it’s the hair and makeup that throw the look off.
With the combination of a beehive and black lipstick, it’s hard to want to nominate her for any best-dressed awards. In fact, the getup landed her on several worst-of lists.
Unisex Black Dress
Well, there have been plenty of stars to grace the red carpet at the Met Gala throughout the years in black lace/sheer dresses – though, for the most part, they’ve been women.
But designer Marc Jacobs decides to mix things up at 2012’s NY event by showing up in this long, see-through shirt dress over a pair of white boxers. Hey, it looks a hell of a lot more comfortable than the majority of other looks on our list, that’s for sure!
Winging It
The theme of 2018’s Met Gala, “Catholic Imagination,” inspired plenty of angelic and devilish attire. Katy Perry did not disappoint when she showed up in a dazzling gold Versace dress with a giant pair of wings.
When she was asked by reporters how she felt in the outfit that night, she responded, “I feel very angelic. Celestial. Ethereal.” It is a stunning look, but it also looks like it’d be heavy – and extremely hard to sit down in.
Borrowed from Grandma
Gwyneth Paltrow’s pale yellow Jimmy Choo dress that she chose for the 2019 Gala has been compared to a “nightgown out of grandma's closet,” with some reporters quipping, “grandma wants her fancy nightgown back!”
The strange neckline that appears almost clown-like doesn’t help her case, either. We will say that this color does wonders for the actress and founder of the wellness brand, Goop.
School Dance
While many stars take their outfits way over the top at the Met Gala each year, actress Jessica Alba decided to roll towards the other end of the spectrum. While she looks decent, it also appears as if she’s gotten dressed to go to a high-school prom rather than such a major event.
It probably cost her an arm and a leg, but it looks like something any teenage girl could go pick up at her local boutique to head to the homecoming dance.
Queen Bey
Beyonce is no stranger to turning heads at events, and the 2015 Met Gala was no different. She slayed in a sheer-looking Givenchy dress after arriving at the carpet fashionably late (like her lyrics say, “I’m so reckless when I rock my Givenchy dress.”)
She’s wearing a nude bodysuit underneath the sheer outing so as not to risk exposing anything to the crowd. This marked this fifth year in a row. She chose Givenchy for the Gala.
Punk and the City
Sarah Jessica Parker, much like the character she played on the hit series "Sex and the City," is known for her ability to dress well. She nailed the "Chaos to Couture" aspect of the punk theme in her gold-splattered leaf-print gown from the Giles fall collection.
She totally could’ve added a mohawk, but instead, she opted for an interesting headpiece and velvet Christian Louboutin boots that pulled the whole look together. SJP for the win once again! But we're not all that surprised, are you?
Walking Tall
Lady Gaga should win some kind of award for being able to walk in insanely high-heeled and often odd-shaped shoes. At 2016’s Gala, she unsurprisingly nailed the "Manus x Machina" concept in a sparkling Versace jacket and sky-high heels.
But there was one part of the outfit that seemed to be missing since she opted for the unitard instead of pants.
Fruit Basket
Cara Delevigne channels Chiquita Banana with her bright-colored getup at the 2019 Gala. But it wasn’t so much the striped rainbow-colored dress or even the scepter. It was the hat that turned heads.
The headpiece she was wearing was covered in fake teeth and eyeballs – one of which she said afterward weighed 10 pounds. Apparently, her scepter broke in the lobby of her hotel on the way to the event, and a stranger lent her a glue gun.
Pieced Together
Model Gigi Hadid seemed to be channeling a bit of French maid with this odd Tommy Hilfiger look that combines a choppy, nude-colored dress with black fishnet thigh-highs.
The whole thing just screamed “mess” and landed her on several worst-dressed lists from the event. Of course, there were a few people who thought the dress, sans the fishnets, looked appealing.
Far Out
Elle Fanning probably couldn’t handle much of anything herself on the night of the 2019 Meg Gala when she appeared in this ‘70s-styled Miu Miu bell-bottom and wing-sleeved salmon-colored outfit.
Each of her nails was done up in something that extended a good inch from her fingertips. But she did do the theme, "Camp: Notes on Fashion," justice with the overall look.
Gold Rush
Cate Blanchett’s golden fringe gown by Balenciaga was a showstopper at the 2007 Gala. She perfectly tuned in to the royal theme, "Poiret: King of Fashion," and accessorized just beautifully, with a golden clutch and turquoise earrings.
The actress rarely disappoints when she makes her red-carpet appearances, so it should come as no surprise that she’s landed on the best-dressed list.
Cinderella
Zac Posen is the magical godfather behind Doutzen Kroes’ Cinderella-like 2010 Gala gown. The dress was designed for the theme: "American Woman: Fashioning a National Identity."
Aside from the gorgeous blue gown, sleek curls and red lipstick were a perfect touch to complete this classic look. There were hardly any naysayers, and comments were, for the most part, raving about the beautiful look. “Now that’s a ball gown,” said one reviewer.
Yellow There
Rihanna appeared at the Metropolitan Museum of Art in 2015 in a yellow Chinese couture getup by Guo Pei, complete with a long, flowing, imperial yellow cape.
The designer is incredibly popular with stars in China, and, since the pop diva reached for her garments, it has started to rise in popularity in the States as well.
First Time’s a Charm
When Celine Dion stepped onto the red carpet at her very first Met Gala in 2017, she was determined to make it count. The singer later reported that when she was getting ready, it felt like a lot, “it’s like getting ready to kiss for the first time, this is huge!”
She opted for a wrap-style Isabel Marant dress, dark headpiece, and matching smokey eyes. Choosing a pair of shoes couldn’t have been easy for her since she claims she has over 10,000 pairs.
Mix and Match
Sarah Jessica Parker’s 2006 dress was a perfect choice for the theme: "Anglomania: Tradition and Transgression in British Fashion." The outfit was designed by the legendary Alexander McQueen and looked just like something her character, Carrie Bradshaw, would wear to go out on the town in "Sex and the City."
SJP rarely lets us down with her Met Gala attire, and this year was certainly no different. It’s been noted as one of her best of all time, according to "Allure" magazine.
A Hairy Situation
Celebrities tend to accessorize with some bizarre stuff at this annual event. Just take Jaden Smith, for instance, who walked around on the carpet in 2017 with a handful of his dreadlocks, which he’d chopped off not long before.
The Louis Vuitton suit he wore and some gold chains looked nice, but the hair kind of threw things off. So, let’s say he lands in the gray area of our list.
Material Girl
The outfit Madonna pulled out for the 2009 Met Gala confused people everywhere. Was she trying to channel her "Like a Virgin" self? The short, puffy dress, thigh-high boots, and strange accessories all screamed, “I’m going to shoot a music video – in the ‘80s.”
The look was a big miss for the night’s theme: "The Model as a Muse: Embodying Fashion." Unless, perhaps, she was traveling back in time to embody the fashion of decades past.
Twins
Jared Leto turned heads – two of which belonged to him – at the 2019 Met Gala when he showed up in this bright red, bedazzled getup. But it wasn’t so much the outfit that landed him on our list, but the fact he was toting a one-of-a-kind accessory that made little sense: a life like replica of his head.
The look was a nod to Alessandro Michele’s “Cyborg” runway show in 2018, where he sent his models down the runway carrying their own “severed heads.”
Bell of the Ball
Claire Danes rocked a Cinderella-esque Zach Posen dress at the Metropolitan Museum of Art’s 2016 gala. The drapey blue gown is stunning on its own, but it’s a fact it glowed in the dark that made it particularly spectacular.
Later, Posen revealed that, even though it may look heavy, it’s actually hollowed out on the inside and, therefore, super lightweight. She wins for that year’s theme: "Manus x Machina: Fashion in an Age of Technology.”
Layer Cake
Cameron Diaz looked like a breath of fresh air when she arrived at 2007’s event in a layered Christian Dior gown in bright fuchsia color. For the "Poiret: King of Fashion" theme, she accentuated her bright-colored, shifty dress with a large, matching turquoise necklace and earrings set.
Apparently, layered dresses were in that year, as the other woman seen here on the red carpet is wearing one as well.
Flower Power
This eye-catching, fuchsia-colored Gucci gown turned all heads towards Jennifer Lopez as she walked the carpet at the 2011 Gala.
Some say that the shrug overwhelms the look a bit, but it received mixed reviews, as others said she carried it well and didn’t let it distract from the overall beauty of the flowy dress. She kept her hair sleekly pulled back and chose to carry a small clutch so as not to overpower the attire.
Swimming in Plaid
Julie Macklowe blended into the rest of the over-the-top looks at the 2017 Gala, even though she looked like a tablecloth mixed with someone who was throwing on random things they found in a Halloween bin in their attic.
Where exactly are her arms? That’s the thing – no one knows. It remains a mystery to this day.
Stun Guns
Supermodel Gisele Bündchen’s look at the 2008 Met Gala has not only landed her on several best-dressed lists of the evening but also lists of some of the best looks she’s ever rocked in her history as a public figure, and that’s saying a lot!
She showed off her lovely figure in a form-fitting, pink satin Versace dress with strategically placed cutouts. The model chose a few classic accessories to adorn the look, along with a fresh-faced glow.
See You Later
It’s easy to see why Anne Hathaway landed on numerous best-dressed lists in 2013. "The Devil Wears Prada" actress walked the red carpet at the Met Gala in a sleek black semi-sheer dress by Valentino.
It was a look that worked perfectly for the "Punk: Chaos to Couture" theme of the year. She accompanied the zig-zaggy dress with a small, black clutch from the same designer and a platinum-blonde pixie.
Classic Hollywood
Taylor Hill walked the carpet at the 2019 Gala looking lovely in a Ralph Lauren dress adorned in Butani and Yvan Tufenkjian jewels. Everything about her look, from the gown to the jewelry to the gloves and hairstyle, screamed “old Hollywood.”
She earned herself a spot on many best-dressed lists that year for her choice in attire. Hill is both a model and actress and has been known for her work as a Victoria’s Secret Angel, which she started in 2015.
What the Puff
The look on the faces of everyone standing behind and looking at Pharell Williams’ wife, Helen, on the red carpet, says it all. It’s the same look that’s probably on your face right now as you’re trying to figure out what on earth she’s wearing, too.
The outfit, a look created by Comme des Garçons, looks like an odd-shaped puffer jumper. Granted, that year’s Gala was based on the avant-garde designer, Rei Kawakubo, the face behind the line. Still, we say, “why?” Or maybe, “what?”
Who Wore it Best?
Well, you may recognize this dress as worn by another certain singer at another major event, but long before J. Lo donned it; Donatella Versace herself wore the Versace gown to the 1999 Met Gala.
The theme that year was "Rock Style," and Tommy Hilfiger sponsored the entire event. Well, the dress looked great both times, so it’s no wonder Lopez chose to wear it the following year to the Grammys.
Nun Other Than
"Baby Driver" actress Eiza Gonzalez nailed the "Heavenly Bodies" theme at the 2019 event when she arrived in this daring Prabal Gurung ensemble, which had a little bit of a naughty and nice flair to it, between the black, cutout front, and trailing white cape.
She may not look like any nun that will be teaching Sunday school anytime soon, but she definitely wins for the best looks of the evening.
That’s a Wrap
Madonna has a thing for baring it all on the red carpet, which was extra apparent when she showed up to the 2016 Met Gala in a Givenchy Haute Couture dress. But it was the black tape that she donned all over her body that really made the look.
But when you’re Madonna going to the Met Gala – you can pretty much get away with wearing anything or nothing at all.
Too Much Fluff
At the 2017 Met Gala, Rhianna arrived in a costume that was beloved by many at the “Rei Kawakubo/Comme des Garçons: Art of the In-Between” themed event.
We don’t know if it’s just that we're really not a fan of the avant-garde or what, but we can’t see what anyone finds appealing about this kind of poofy, bizarre style. However, she did stick to the theme beautifully, showing up in a look done by Rei Kawakubo herself.
Ages Past
Supermodel Amber Valletta holds a special place in her heart for the Models as Muse Met Gala since some of her own work was being commemorated, so the entire event really hit home for her.
But at 2004’s Gala, she arrived in this Maggie Norris Couture corset and John Galliano skirt that really nailed the "Dangerous Liaisons" theme. In no other place in the modern world would this look make sense than the Met Gala…
Lights, Camera, Action!
Katy Perry makes our list, and she will do it again. Oddly enough, she’s literally wearing lights. Back in 2010, she had lights look that was slightly more subtle, if that’s even possible, for dresses created with lights.
But at the 2019 Met Gala, she’s decked out like a full-blown chandelier – headpiece and all. The outfit designed by Jeremy Scott doesn’t look so much like an outfit as a Halloween costume.
Read on to see some of the most timeless Oscar outfits of all time
Going to the Oscars would be a dream for most of us. It’s a once-a-year event that has everyone excited-even the people who can’t or won’t attend. This day is marked on the calendars of many. It’s certainly an event that you don’t want to miss.
While some celebrities are dressed in the most beautiful gowns, others wear dresses that are a bit over the top and questionable. Hang on to your seats because some of these will have you wondering what some of these celebrities were thinking.
Rihanna
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!
Farah Fawcett
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.
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.
We absolutely love it.
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.
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 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.
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’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.
Charlize again
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.
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.
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.
Liz Hurley
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.
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 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.
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.
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 English Rose. The cross-shoulder is the perfect touch to such an elegant yet simple gown.
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 looks incredible on her.
The gold leaf detailing on the dress is to die for.
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.
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?
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.
Emma Thompson
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.
Kate Upton
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.
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.
Cindy Crawford
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.
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!
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.
Jennifer Lawrence
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.
Miranda Kerr
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.
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.
Celine again
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.
Whoopi Golberg
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.
Madonna
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.
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 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.
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 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.
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 where she won the Oscar for Best Actress.
This dress became an instant classic and she looks beautiful in it.
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.
Bella Hadid
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!
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.
Kendall Jenner
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.
Lady Gaga
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.
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 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.
Gigi Hadid
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.
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 1920’s 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 Angelia’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 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.
Zendaya
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.
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.
Irina Shayk
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.
Emily Ratajkowski
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.
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 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.
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 trail of feathers that just hit it out of the park.
Halle Berry
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.
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!
There aren’t too many people who could pull off a dress like this.
Katy Perry
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.
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 in 2019. It reminds us of something right out of the Princess Diaries
Marion Cottilard
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.
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.
She sure did improve in later years with her outfit choices.
Celine Dion
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.
Cher
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!
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 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.
Jennifer Lopez
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.
Grace Kelly
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.
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. If someone wore this look today, no doubt they’d be on the best-dressed list.
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 consists of cutouts only a stunner like her could rock.
Lady Gaga
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.
Barbra Streisand
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.
Kasey Musgraves
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.
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.
Kate Winslet
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.
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 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.
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 impressive train. Aniston topped off the look 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
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.
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 Robinhood-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 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.
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 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 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, 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."
Cate Blanchett
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.
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.