Miley Cyrus, 2013
Making her debut in 2008 as a young "Hannah Montana," Miley Cyrus quickly shed her innocent appearance. In 2013, the young star had a particularly raunchy coming-of-age moment. The world watched in shock when she performed "Blurred Lines" with Robin Thicke and showed off her crazy twerking skills.
This cheeky, not-so-innocent outfit was a result of her journey to break free from her Disney-star image. Cyrus hosted the MTV Awards show two years later, where she wore some of the most risqué outfits ever seen on the red carpet. She’s the undisputed reigning queen of the VMAs if there ever was one!
Geena Davis, 1992
In the early ‘90s, Geena Davis was at the height of her career (and that wasn't a tall-people joke, she really was one of the busiest actresses in the industry.) While many expected her to turn up to the Academy Award ceremony in 1992 in a sleek and luxurious gown, the opposite happened.
The actress instead donned a dress designed by Ruth Meyers and Bill Hargate that was short at the front and long at the back. As if that wasn’t enough, there were a lot of ruffles and opera gloves to contend with. The whole thing shook many fans to the core, and they couldn’t believe what they were seeing.
Lady Gaga, 2010
We can't have a list of looks without including Lady Gaga, no matter what the woman is dressed in. If we could, we would have added all of her outfit choices to the list of the most memorable red carpet looks. Unsurprisingly, you will find her featured here more than once.
Gaga donned this weird and wacky ensemble to the 2010 Brit Awards, and the Francesco Scognamiglio design certainly went down a storm. As if the giant wig wasn’t enough to weigh Gaga down, we have a feeling that this huge amount of material probably did it for her.
Lil Nas X, 2022
Did someone say drama? Because Lil Nas X brought all of it to the red carpet at the 2022 MTV Video Music Awards. Although dubbed the "industry baby," the rapper was anything but doe-eyed at the VMAs. He arrived in a pair of shiny black pants, a shiny feather-cage overskirt, and a matching headpiece, instantly making an unconventional statement.
The look came together with gorgeous diamonds from De Beers. He looks like he stepped straight out of the sets of “Black Panther.” Known for his boundary-breaking sense of style, the rapper, once again, did not disappoint! Who said little when talking about the black dress?
Rooney Mara, 2016
Rooney Mara is a fashion sensation who fearlessly experiments with her style. Whether it's bold hairstyles or statement-making clothing, she never shies away from taking risks on the red carpet. But what sets her apart is how effortlessly she pulls off these looks without looking too over the top.
At the 2016 Golden Globes After Party, Mara rocked a stunning ruffled Alexander McQueen gown paired with a braid that perfectly complemented her edgy style. She and co-star Cate Blanchett were both in the running for the Best Actress award that night. While Mara didn’t take home an award, she was already a winner on the red carpet and in her fans' eyes.
Kate Middleton, 2019
Although Kate Middleton and the rest of the Royal Family don’t always attend events surrounding popular culture, both Kate and her husband made their way to the BAFTA Awards in 2019. Not one to shy away from designer labels, the Duchess of Cambridge wore one of her favorite designers that night — Alexander McQueen.
Alexander has been by Middleton's side for a few years now and has managed to bring out the best in the stunning princess. This white one-shoulder gown featured light and flowing material and allowed Kate the chance to show off the beauty and simplicity of the design. She looked stunning, and Prince William didn’t scrub up too badly, either.
Amanda Seyfried, 2013
Amanda Seyfried was discovered by a modeling agency in a town in Pennsylvania, and she has been killing the game ever since. At this Oscars event, she wore an Alexander McQueen gown which looks incredible on her. She wears it with such grace and seemingly zero effort. It's much more difficult though to pull off than it looks.
The gold leaf detailing on the dress is to die for. Of course, Seyfried is much much more than just a pretty face. She has delivered some pretty stellar performances over the course of her career — and she's still so young. She received much applause for her role in the Hulu miniseries "The Dropout."
Penelope Cruz, 2018
The Spanish-born actress has been a superstar in the industry for more than three decades. Over the years, she has earned herself several awards making her one of the most successful email actors of the 20th century. Penelope Cruz made a striking entrance in this black lace Ralph & Russo gown.
The off-the-shoulder dress with full-length lace sleeves radiates elegance. At the 75th Golden Globes on January 7, the red carpet saw mostly black gowns in recognition of Time’s Up, a legal defense organization for women. All but three red carpet invitees dressed in the all-black theme. Cruz paired her gown with Christian Louboutin heels and sparkled with Atelier Swarovski.
Liz Hurley, 1995
Liz Hurley turned heads on this red carpet for a number of reasons. One was that the man on her arm was fellow British actor Hugh Grant. The other is 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. Although the couple ultimately weren't meant to stand the test of time, they were very pretty to look at. And during the 90s, both actors were the performers that every filmmaker wanted to work with.
Marilyn Monroe, 1962
Marilyn Monroe won what would be the final award of her career when she attended the Golden Globe Award ceremony in 1962. Her sleek gown, a full-length dress ornately embroidered with sequins, sparkled in black. It was designed for her by Norman Norell. It is one of his most famous designs ever.
The snug-fitting dress, which was also a part of her personal wardrobe, featured a V-neck top and a backless back. She collected her Golden Globe for “World’s Favorite Film Star” at the event. Monroe is always associated with her white blowing-in-the-wind famous piece, however, as you can see, there is much more to the legend.
Meryl Streep, 2013
It's an honor for any designer to have an A-list celebrity wear their looks on the red carpet. So imagine how it must feel knowing Hollywood royalty like Meryl Streep will be donning one of your dresses! To match the glistening awe that is Meryl Streep, design house Lanvin provided an all-over-sequins dress with a deep V-neckline, topped with floral, sequin flower shoulder pads.
Streep may only have been a presenter that night, but she outshone a lot of the winners. Realistically, she could have done that wearing a trash bag, but a designer dress is just so much more fun. Oh yeah, she was also 64 when she rocked this look. No biggie.
Emma Roberts, 2018
All grown up, Ms. Roberts is still pursuing an acting career. She played Jess in "Who We Are Now" in 2017 and also starred in the ninth season of "American Horror Story: 1984." In March 2019, Emma hooked up with fellow actor Garret Hedland of "TRON: Legacy" fame. The two welcomed a child into the world together in December 2020.
Sadly, the two lovebirds announced their split in January 2022. If we put Roberts's personal life aside and focus on her magnificent dress, there are no sad announcements to make. No surprise here, and Emma takes after her aunt and looks remarkable in this almost royal black dress.
Lupita Nyong’o, 2014
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 no 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 space 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.
Zendaya, 2016
Zendaya has been slaying on the red carpet for years. The actor was in her element in a stunning ruby-red Marchesa dress at the 2016 Golden Globes. As gorgeous as red carpet dresses are, they can seriously cramp your style when it's time to let loose, but not for Zendaya, who refused to let a voluminous gown get in the way.
With the help of her longtime stylist Law Roach, she quickly transformed her elegant floor-length gown into a fun and flirty cocktail-length dress — just right for tearing up the dance floor at after-parties. She inspires us to strike the right balance between looking incredible and living in the moment.
Mariah Carey, 1991
Three years before her world-famous (and unavoidable) Christmas album, Mariah Carey attended the 1991 Grammys for her nomination as Best New Artist. The diva won the award that night and looked spectacular while doing it. Here we see a 20-year-old Mariah wearing a classic, black strappy dress and a silver neckline.
She wore matching, long silver earrings and defined cascading curls to show off her beautiful mane. Nowadays, it’s rare to see Mariah styling anything other than a super straight hairdo. The Christmas Queen has recently left Hollywood and gone back to live in New York, where she grew up.
Cher, 1986
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 (or jill?) of all trades. And although she is approaching her 80s, she still looks incredible.
RuPaul, 1993
RuPaul is the ultimate drag queen, author, talk show host, and actor extraordinaire. Despite wearing many hats, this multi-talented superstar looks stunning every time. And he brought his A-game to the 1993 VMA looking all kinds of fabulous. No surprises there! Sadly, most people remember less of the dress and more of the infamous altercation between RuPaul and Milton Berle.
Berle allegedly mistreated RuPaul backstage before their on-camera appearance together at the show. Berle then went on stage and inappropriately touched Mama Ru, referring to him with an offensive pronoun. RuPaul was having none of it, of course! Since the incident, it's safe to say that RuPaul has come out on top.
Chloë Sevigny, 2009
"Boys Don’t Cry" star Chloë Sevigny entranced red carpet spectators with a translucent polka dot gown by Issac Mizrahi. The actress accented her sheer, one-shoulder dress with a shiny yellow-gold bracelet and a brooch on the hip. The dress wraps the actress in great comfort, and the loose fabric on the side and bottom of the dress couldn't be more precise.
This dress was made especially for Chloë Sevigny. It emphasizes her feminine and natural curves. A white dress can sometimes do wrong on a very pale skin tone and wash it out, however, in this case, she just shines even more.
Lil’ Kim, 2000
As the unofficial queen of outrageous outfits at the VMAs, Lil’ Kim did not disappoint with the plastic red outfit she wore to the 2000 awards show. Wearing a bustier romper made out of red transparent plastic, the “Lighters Up” rapper topped off her look with a matching bright red plastic jacket.
With all of those straps, studs, and sharp plastic edges, we just can’t imagine how uncomfortable this outfit must have been. On the bright side, with that PVC jacket, she was probably ready for any sort of rainy weather! Well, at least select parts of her body were, anyway.
Gigi Hadid, 2015
Between Gigi and her sister Bella, we are not sure who turns heads more. It does not 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 are not sure that just anyone could have pulled this off, however, on her, the very unique design seems to fit perfectly. These days the models continue to walk the runway and turn heads no matter where she goes and what black (or other) dress she is wearing.
Meryl Streep, 2012
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.
Saoirse Ronan, 2018
This custom Atelier Versace gown was modified for Saoirse Ronan. A team of all-women worked on the “Lady Bird” actress’ Golden Globe look. From makeup to designers, Ronan requested women create her style. The originally all-black asymmetrical Atelier Versace was altered most noticeably with bold silver accents on the left shoulder and up the right side.
Her team chose Cartier jewels. The diamond and sapphire drop earrings set off her eyes, and a wide cuff bracelet completes the silver adornment. Ronan rose to fame after starring in the 2007 movie "Atonement," and since then, she has added a few notable screen moments to her resume.
Miley Cyrus, 2018
As hard as it might be to believe, there was a time when Miley Cyrus wore traditional gowns for red carpet events. For the Grammy Awards ceremony in 2018, Miley Cyrus wore a Zac Posen ball gown that made her look like a princess.
We know Miley was going through a lot around 2018, but no matter what your stance on her, you have to admit that this dress was made for her. And her performance alongside legendary Elton John probably made her feel even more like a princess. The deep red dress was accessorized with a classic, old Hollywood hairdo and subtle makeup.
Charlize Theron, 2016
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 changes are so radical, it's hard to wrap your head around it. 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.
Nicki Minaj, 2012
It seems as though Nicki Minaj can't get enough of making fashion statements. By the time the 2012 Grammy Awards came around, this singer and rapper went with an entirely unexpected look. Instead of rocking the animal print, she rocked her habit-like cloak dress.
While the Versace ensemble was supposedly an homage to Madonna, many people were offended rather than impressed. They believed her own outfit to be sacrilegious, and that’s before they got onto the fact that she brought along a date dressed as the Pope. We're all for celebrities taking risks on the red carpet and making political or social statements, but this... didn't make the cut.
Trey Parker and Matt Stone, 1999
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 to get 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 something like this off.
Taylor Swift, 2016
Taylor Swift has been working in the music world for years now and she is constantly trying to reinvent herself when it comes to her sound and her fashion choices. While the hit-making singer has had a number of styles that we love, this modern and revealing dress is one of our favorites.
Her blunt haircut and the asymmetrical lines and slits on the dress make it seem like she just walked out of a time machine. These days the talented star is working on directing, moving, and writing new lyrics, and continues to amaze us in magnificent black dresses.
Halston Sage, 2020
Halston Sage brought serious style game to the 2020 Golden Globes after-party, stunning in a bold and intricate Galia Lahav Spring 2020 embroidered dress that left everyone buzzing. The dress featured a sheer, form-fitting design with delicate floral embellishments and lace that trailed down the gown's length.
Sage's confident and effortless presence added to the striking beauty of the dress, making it one of the finest looks of the evening. Her personal style always impresses, featuring bold and fearless statement pieces that most of us wouldn’t dare try. It takes a queen to pull off a look like this, and there she was, in the flesh!
Judith Light, 2015
With her breakout role in “One Life to Live,” Judith Light quickly captured viewers' and critics' hearts. But it was her role as the sharp and sassy Angela Bower in “Who's the Boss?” that truly made her a household name. Impressive acting abilities aside, Light is also celebrated for her impeccable outfits both on and off the red carpet.
At the 2015 Golden Globes after party, she made a statement in a classy green fishtail gown. Her natural makeup and hair completed the look, cementing her status as a fashion icon. The look reflected her personality and unique aesthetics. Some people are timeless and never fall out of fashion.
Kendall Jenner, 2016
With her model physique and her beautiful face, Kendall Jenner is no stranger to showing off what her mother gave her. She has been doing just that since she first made her celebrity debut, and it became extremely apparent at the MTV Movie Awards in 2016.
While her black dress was floaty and feminine, it was her shoes that really caught us off guard. It's safe to say that celebs are known for wearing high heels as it is, but this particular pair took that to the extreme. As if that wasn’t enough, you couldn’t just whip these off in a hurry.
Carrie Underwood, 2017
Country queen Carrie Underwood always serves great looks regarding red carpet events. For the 2017 Grammy Awards, cutie Carrie Underwood wore a fiery red Elie Madi gown with shiny red beaded details and a sensual keyhole front. This kind of outfit makes us think she was trying to make someone jealous. Just imagine seeing the girl you dumped in high school on the Grammy red carpet wearing this!
The beautiful long-sleeved sheer dress was the perfect combination of elegance and boldness. Her understated jewelry and shoes were the perfect accessories to complete the look. She might have an all-American sweetheart face, but Underwood certainly cleans up well for awards ceremonies.
Bella Poarch, 2021
Bella Poarch is a popular social media star and singer. In 2021, she went all out with this gothic meets glam ensemble. The TikTok star wore a sheer black jumpsuit with ruffled flared pants and a matching black shimmering cape to that year’s VMAs. It was definitely quite the show-stopper.
Bella finished her look with a long dramatic train that even required special assistance on the red carpet! Though the awards ceremony took place in September, this outfit gives us Halloween vibes of the best kind — especially when we zoom into her amazing nail art featuring black and white snakes.
Lil’ Kim, 1999
1999 was quite some time ago, and yet there are few fashion moments as memorable as rapper Lil’ Kim wearing a lavender jumpsuit with just a seashell-shaped sequined pastie covering the other side of her chest. The rapper came out to present the "Best Hip-Hop Video" award with icon Diana Ross.
And in case her outfit wasn’t jaw-dropping enough, Ross actually outstretched her hand and gave her co-presenter a jiggle! Oh, and if you’re wondering just how that pastie stayed in place — her stylist used eyelash glue. We don't even want to think about how uncomfortable that was to take off.
Lupita Nyong’o, 2014
All eyes were on Lupita Nyong’o at the 71st Golden Globe Awards. And can you blame us? The dazzling model and actress was one to watch, having turned heads on fashion runways during the 2014 season. On the red carpet, she continued to show everyone what she was made of.
She was also an up-and-coming film star, nominated for Best Supporting Actress. Nyong’o chose a red statement gown by Ralph Lauren, even though she was the face of the Miu Miu fashion house. The actress, who is also a Yale School of Drama graduate, donned the dramatic dress that featured an attached cape with the skilled finesse of a supermodel.
Lucy Liu, 2019
Dubbed "The Loofah Dress," Lucy Liu's purple look at the 2019 Tony Awards was definitely a show-stopper. Liu is, bewilderingly, over 50, but age is clearly just a number in this case. This not-so-subtle number certainly made a statement, and just to top it off, it's in a gorgeous purple hue (in case you missed her.)
Wearing Christian Siriano, the "Charlie's Angel" star sported minimal makeup, because when you age as gracefully as Lucy Liu, you don't feel the need to slather on a full glam look. Liu topped off the look by accessorizing with green earrings and a matching purse.
Kim Kardashian, 2021
This would have worked great for the premiere of any "Matrix" flick, but otherwise, it's a bit too futuristic for us. Kim wore this for the People's Choice Awards. The ceremony was held in December 2021, so at least she was warm. Maybe she was trying to cosplay as a superhero?
If Superman wears his underwear on top of his clothes, Kim can wear her bra on top of hers as well. This is a great way to call for equality between men and women! Kim took it a little too far, in our opinion, however. You know what they say — there is no accounting for taste.
Audrey Hepburn, 1975
Literally the epitome of classic Hollywood glamour, Audrey Hepburn absolutely stunned at the 1975 Academy Awards red carpet in a dazzling 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. In her prime, Audrey Hepburn was the leading woman in the industry. Men admired her, and women envied her, for she had it all. She was stunningly beautiful and led fashion trends. She was the diva of her era.
Marisa Tomei, 2019
The 2019 Emmys were bursting with iconic looks, and all eyes were on the nominees, but also on the gorgeous presenters. So when Marisa Tomei booked a gig presenting, her style team really went to town. The result was a one-shoulder, two-toned fuchsia and red gown by Ralph & Russo Couture.
This dramatic look, paired with some pointy silver pumps, ensured that Tomei would not fly under the radar for a minute. Mission accomplished! We don't even care what award she was presenting or who won it. And we have a feeling that most people that night felt the same way.
Salma Hayek, 2018
Salma Hayek's 2018 Oscars look would have been a tough one for anyone to pull off. There's a lot of bling and sparkle going on, and never mind the way this pink, sequined Gucci dress hugs the body. But at 52, Salma Hayek pulled it off like it was nothing. Hayek is no stranger to dramatic looks that show off her figure, so why would this look be any different?
As the saying goes, don't fix what isn't broken. Rocking an hourglass figure that most women could only dream of, Hayek even doubled down on the drama by wearing diamond chandelier earrings and sporting a burgundy lip shade.
Kate Hudson, 2016
Kate Hudson wears many hats — an accomplished actress, a Hollywood legend, and a fashion icon. She's well known for her impeccable sense of style that's both trendy and timeless. Her wardrobe choices have inspired countless fashion enthusiasts around the world. When off-duty, Kate prefers a bohemian look and flowy dresses.
When it comes to red-carpet events, she knows how to take it up a notch or ten! At the 2016 Golden Globes After Party, Hudson stepped out in a glamorous nude-colored two-piece, featuring a strapless top, a fitted skirt, and a matching choker necklace. Minimal but boy, was it effective!
Lil Nas X, 2019
What do you do if you have a bullfight followed by a disco dance party? You throw on this sparkling bullfighter-inspired outfit worn by the controversial rapper Lil Nas X. The artist wore this blinding silver sequin suit to the 2019 VMAs.
Complete with lace accents and metallic heels, his outfit was one of the most memorable of the night. We love how he managed to put his own twist on the traditional tuxedo by pairing a cropped bolero jacket with matching silver pants. Little did everyone know at the time that this was just the beginning of Lil Nas X's crazy award show looks.
Sinéad O'Connor, 1990
In 1990, Sinéad took home three MTV Music Video Awards, including Video of the Year, Best Female Video, and Best Postmodern Video for "Nothing Compares 2 U." Her signature defiance was in full play during the performance. She performed in a loose-fitting white maxi dress, teasingly revealing her sexy black slip underneath. Well, if they wanted a skin show, she would do it on her terms!
The singer completed the look with oval sunglasses and Doc Martens. Few artists have rocked the boat like Sinead O’Connor, who defied tropes of what artists “should” be. She can wear whatever she wants, and she will forever preserve her spot in the best artist of the 1990s list.
Grace Jones, 1983
Jamaican-born model and singer Grace Jones has been a fashion icon since the 70s. Her disruptive and bold fashion choices have made her one of America’s most famous models, stunning everybody at every event with her unique outfits. Here we see Grace Jones attend the 1983 Grammy Awards in an avant-garde, science-fiction-themed black leather-straw outfit.
Her ultra-wide brim hat that looked more like an umbrella than an accessory. She paired the look with jewel-toned, purple eyeshadow, hot pink blush, and flawless red shiny lipstick. It's been a few good decades since this picture was taken, however, this has not stopped Jones from staying on stage and showing the world what she's got.
Mila Kunis, 2009
For the 2009 Emmy Awards, Mila Kunis went with a Monique Lhuillier gown. The "Black Swan" actress sparkled in the dainty burgundy tulle cocktail-length dress trimmed with a black waist tie. Even though this was all the way back in 2009, this is easily one of Kunis' most memorable looks.
It's different and unique while not being a crazy divergence from mainstream haute couture. We do think that while the cocktail length is fun, the dress might have looked better as a full-length gown. Still, the length allows for Kunis' cute shoes to be shown off, and they match perfectly. The beautiful actress finished it off with Fred Leighton jewelry.
Carmen Electra, 1997
Carmen Electra certainly was bearing all in this barely-there piece. While the front of the dress is pretty demure, the side...slit... is shocking, to say the least. To be completely honest, if we looked half as incredible as Miss Electra does, we would be wearing this dress in a heartbeat!
Electra was born Tara Leigh Patrick, and after arriving in Hollywood, she wanted a name that would fit the scene. She was discovered by the one and only Price, who auditioned for an all-girl band back in the 1990s. The entertainment world is definitely not the same without him, and could you imagine what the world would have been without her?
Rihanna, 2010
Rihanna is definitely a star who knows how to clean up well and be red-carpet-ready. She offset her flaming curls with a breathtaking blood-red Elie Saab gown at the 2010 American Music Awards. Riri's red hair phase led to some of the singer's most iconic outfits, and clearly, the red gave her some extra confidence.
The gown was from Elie Saab’s Fall 2010 Couture collection. She looked as glamorous as ever. She also scooped up an award that night for best Female R&B Artist. So, all in all, it seemed like a pretty good night for the Barbadian beauty!
Joey King, 2020
Joey King turns heads with her fashion choices, and her appearance at the Golden Globes 2020 was no exception. The actor looked absolutely stunning in a jaw-dropping black and white Iris Van Herpen dress that had us seeing double with its optical illusions. The dress featured ruffles just above the knee, a sheer high neck, and some seriously bold shoulder cutouts.
But the pièce de résistance was the dramatic black and white striped "wings," fluttering on cue behind her as she walked the red carpet. King's style evolution is a true inspiration, and we can't wait to see what she'll bring to the next red carpet event.
Angela Bassett, 1994
At the 51st Golden Globe Awards in Beverly Hills, Angela Bassett stole the show. Not only did she win the Best Actress prize for her portrayal of Tina Turner in “What’s Love Got to Do with It,” but she also won big on the red carpet. Her gown featured satin and lace, with one side of the bodice in satin and the other in lace. Around the waist, the lace and satin came together with peplum trim.
This was Bassett’s breakout role, and she did the award circuit in style. We have a feeling we are going to hear a lot about her in the future, and she will adorn not only our screens but the red carpet, too, on her way to grasping some more awards.
Lil Nas X, 2021
There are some artists who are known for pushing the limits — not just with their music, but also with their fashion. Lil Nas X can always be counted on to bring unforgettable lewks to the VMAs, and his appearance in 2021 was no different. While this whole look is definitely out there, you have to admit it's a gorgeous color and suits the rapper nicely.
The rapper wore a dangerously low-cut, bedazzled lavender Atelier Versace suit with a matching shimmering train. The crystal-encrusted creation helped dub him the best dressed on the red carpet. While the craftsmanship of this outfit is amazing, we really can't get past his 1980s-style mullet.
Lady Gaga, 2009
When it comes to VMA fashion, no one does it better than Lady Gaga. The singer-turned-serious-actress flaunted a total of five different outfits throughout the show, each stranger than the one before. When accepting the award for "Best New Artist" in 2009, Gaga changed into something a bit more comfortable — a red Alexander McQueen dress with a matching face cover and crown.
The unique outfit seemed to stun award presenter rapper Eminem who couldn’t hide his confusion over the singer’s strange getup. Little did Eminem know that she would be returning with an even crazier outfit (ahem, her infamous “meat dress.”)
Renée Elise Goldsberry, 2020
Despite the fact that the 30th Annual Gotham Awards had a virtual ceremony, celebs still put their best feet forward, including "Hamilton" star Renée Elise Goldsberry. Wearing a daring look from Naeem Khan, the actress turned heads (albeit virtually) in this sparkly red jumpsuit with a plunging neckline.
Given that Goldsberry was 51 here, it's pretty impressive to see she doesn't look a day outside of her 20s. Her confidence is palpable, and who can blame her? The woman knows how to style! She completed the look with a giant sparkly silver bracelet and a bag that, honestly, maybe wasn't the best choice. Still, it's a hard yes from us.
Taylor Swift, 2014
Sure, a short romper isn’t the most scandalous VMAs outfit, especially compared to the body-baring outfits worn by most celebrities. Still, this risky romper was quite an unexpected outfit for Taylor Swift. The singer, more known for break-up songs and “cottage-core” French braids, surprised everyone with this leggy look.
Taylor, who usually plays it safe and classic on the red carpet, decided to switch things up for the 2014 ceremony, and fans absolutely loved it! Since this appearance, Taylor has been one to watch on the red carpet with her edgy style. Her short hair was also shaggier than usual, and the tousled locks suited the ensemble perfectly.
Rihanna, 2011
It's no surprise seeing Rihanna pull off a see-through look, although this may be one of her most outrageous looks to date. While a lot of people might look tacky in this white, furry, off-the-shoulder number, Rihanna pulls it off unassumingly with strategic sewing and an impressive amount of confidence.
She rocked this dramatic sheer Jean Paul Gaultier Couture spring/summer 2011 dress to collect her award for Best Dance Recording at the 53rd Annual Grammy Awards. When Rihanna finds a style she likes, she sticks to it, rather on a shorter cycle than the average person. And she has the means to afford her ever so changing style.
Shania Twain, 2022
Everybody should just stop what they're doing. Shania Twain just made the best/boldest/weirdest/most iconic fashion choice of 2022. The country star was honored with the Music Icon Award at the 2022 People's Choice Awards, and she did not disappoint.
An ode to the music video for her legendary song, "That Don't Impress Me Much," Twain wore a leopard-print dress, equipped with a hood and all. Also featuring a sheer body suit, this look sent fans into a nostalgic tizzy. This would be like Britney Spears bringing back the all-denim look from her Y2K days. And pulling this off at 57? That certainly does impress us much.
Diane Keaton, 2004
Diane Keaton looked elegant and sophisticated on the red carpet at the 2004 Golden Globes. In all white, she wore a Nehru jacket, long gloves, and an extravagant string of pearls. She looks winning, and win she did. Keaton won the Best Actress prize for “Something’s Gotta Give.”
Accepting the honor, she gushed over the fact that she had the rare opportunity to play the female love interest at her ripe age, almost ending her 7th decade in life. With those sparkling boots and silky, glossy gloves, Keaton knocked off a few years and blended in flawlessly with the younger generation.
Catherine Zeta-Jones, 2021
When Catherine Zeta-Jones showed up on the 2021 Emmys red carpet, everyone else might as well have gone home. Her strapless, burgundy gown turned heads with its high slit and cinched waist. The Welsh actress looked like the perfect blend of elegance and seduction — not an easy feat in general, let alone doing it in her 50s.
Her husband, actor Michael Douglas, told reporters, "I can't believe my luck." We wouldn't either, Michael! The dress was the work of Cristina Ottaviano, a New York-based designer who has also dressed the likes of Bella Hadid, Allison Janney, and Emily Ratajkowski for their red carpet-dos.
Hailey Bieber, 2020
Hailey Bieber swept the style awards at the 2020 InStyle and Warner Bros. Pictures Golden Globes after-party in Beverly Hills. The model dazzled in a stunning glittery Saint Laurent blazer dress complete with a plunging neckline. Adding a touch of edge to her outfit, Hailey sported a loose leather belt around her waist.
Known for her impeccable street style, the model always turns heads whether she is enjoying some downtime in LA or strutting down the runway during fashion week. What truly sets her apart is her skillful use of oversized outerwear as the final finishing touch to any outfit.
Angelina Jolie, 2012
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 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."
Madonna, 1991
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 of Pop on her arm as her date.
Isn't that just the most stunning image you have ever seen? Here we have, outside of Elvis, arguably the two most influential pop stars of the last 100 years, holding hands and looking absolutely incredible. Madonna and MJ had huge love and respect for each other and only wanted to see each other succeed.
Miley Cyrus, 2015
Wearing just slightly more than she did in her “wrecking ball” music video (aka nothing), Miley decided to wear this futuristic and practically non-existent outfit to the 2015 VMAs. Wearing chandelier-inspired underwear and metallic suspenders, Miley pushed the limits of body glue when she stepped onto the red carpet in this revealing look.
Surprisingly, this was just one of a lineup of similarly revealing outfits that included a completely transparent plastic dress with carefully placed dots. We’re not sure how cold it was in the auditorium, but we hope someone had a sweater to lend her! At least her legs were warm.
Audrey Hepburn, 1990
Hollywood legend Audrey Hepburn, who is beloved for her role in “Breakfast at Tiffany’s,” was at the 47th Golden Globe Awards for a special reason. The Golden Era actress was honored that night with the special Cecile B. DeMille award. She looked absolutely stunning in a white satin column gown. Hepburn’s sheer elegance gave that 1990 ceremony a special ambiance.
Audrey wore a timeless piece. A pure white gown that would never go out of fashion and remain classic for eternity, just like the star herself. Hepburn represented beauty and glamour and didn't need more than a plain yet elegant dress to stand out.
Patricia Clarkson, 2019
It's hard to believe that at just shy of 60, Patricia Clarkson was rocking the red carpet, putting to shame actresses half her age. But that's what happens when you have an A-grade stylist who secures you the latest Zuhair Murad fresh from the runway.
Needless to say, nobody spoke about the 2019 Screen Actors Guild Awards without mention of Clarkson looking like a real-life goddess. That probably softened the blow when Clarkson missed out on the award she was nominated for. But hey, Clarkson has racked up her fair share of awards over the years, so we're sure missing one here and there isn't so tough for her anymore.
Mandy Moore, 2017
Mandy Moore was a red-carpet sensation at the 2017 Golden Globes. The actor was in the running for the Best Supporting Actress award for her role in “This Is Us,” but she stole the show with her black dress! Moore wore a fabulous sheer gown that left little to the imagination, designed by the legendary Naeem Khan. The dress made her look every bit like the stunning goddess she is.
She said she felt like a quasi-superhero, thrilled to don a cape for the first time. It’s safe to say she looked and felt the part! To complement her ensemble, Moore wore exquisite teardrop earrings and a diamond bracelet and carried a sapphire blue clutch.
Adele, 2012
This British singer and songwriter won over the hearts of us Americans with her first single. To date, the singer has won numerous prestigious awards including an Academy Award, a Golden Globe, and over 15(!) Grammys, with many more to come, we're sure.
We have seen her in all shapes and sizes and no matter what she wears or how much she weighs, in our opinion, she always looks amazing. In this photo, she is wearing a beautifully cut dress that highlights her small waistline and blurs out parts that are less flattering. It's one of those dresses that will never date and will always stand out in a crowd.
Amber Heard, 2016
Amber Heard arrived at the 2016 Golden Globes in this showstopper that worked on every level. It’s hard to stop staring at the coral-pink Gucci gown, partly because it looks just as fantastic from the front as it does from the back. It's not over the top, but it commands attention and is undoubtedly elegant.
A floral embellishment rounds her neckline, and the décor continues down her back. The chiffon fabric gives the actress an ethereal air. The actress donned a vintage-inspired hairdo (with a pretty crisp wave, mind you) and scarlet lip color to complement the floral design sealed the deal.
Lady Gaga, 2010
When it comes to coming up with unforgettable VMA fashion, there is no one like Lady Gaga. In 2010, the artist seemed to be inspired by the meat selection at her local butcher. Wrapped in layers of actual meat, Gaga showed up at the award ceremony in what is considered to be one of the most famous moments in award show history.
While the dress, according to Gaga, was intended to symbolize a protest against the “Don’t Ask, Don’t Tell” policy of the military, it didn’t stop the endless amount of jokes and talk about the gory getup! It's hanging in a museum somewhere today, we're told.
Iman, 2017
Supermodel Iman has dedicated decades to charity work and outreach, so spotting her on the red carpet for the amfAR New York Gala is no surprise. As a sponsor of the evening, Iman stunned in a red, satin Zac Posen number with a diagonal design.
Iman has been honored at countless events and won awards galore, so even though this isn't technically an awards show, we let it slide. The model was 61 at the time but easily stole the show as one of the best-dressed. Considering this is the annual kick-off event to New York Fashion Week, that's no small feat.
Jessica Biel, 2018
When “SexyBack” singer Justin Timberlake married actress Jessica Biel, it seemed that they had one of the most adorable relationships. The talented couple was known for their frequent appearances on the red carpet and adorable social media posts. At the 70th Primetime Emmy Awards in 2018, Biel wore a beautiful dress with a crescent pattern from top to bottom. The transparent fabric upgraded the simple cut, which ended with a unique and interesting design.
In recent years, Justin has come under fire for his past behavior with his ex, Britney Spears. He also ignited a gossip storm when he was snapped getting a bit too close to his “Palmer” co-star, actress Alisha Wainwright. In response to the criticism, the couple admits they work hard to weather the “ups and downs.”
Jada Pinkett Smith, 2022
In her first red carpet appearance since the infamous 2022 Oscars incident, Jada Pinkett Smith returned to the public eye and she did it with a bang. The actress wore a bold high-low gown from Stéphane Rolland, kitted out with embroidered crystals and a long, dramatic, ruffly train.
Even though there's a lot of fabric going on, the star, who is notably petite, stunned and didn't let the look overshadow her natural beauty at all. Jada's face is unique and exquisite and shows that no long locks are needed when you have such a captivating look and a special face.
Helena Bonham Carter, 2021
Compared to some of HBC's other looks, this one doesn't even seem all that eccentric. Still, this white ruffly gown with black polka dots perfectly embodies the quirky, free spirit that is Helena Bonham Carter. The actress was 55 years old when she attended the 2021 BAFTAs, arm-in-arm with her boyfriend, Norwegian writer Rye Dag Holmboe, who is 21 years younger than her.
Considering she's so young at heart and he is "an old soul in a young man's body," according to Bonham Carter, it looks like a match made in Tim Burton's version of heaven! (Or his version of hell, depending on who you're asking.)
Angelina Jolie, 2004
Angelina Jolie is one heck of an actress who may be mostly known for her role in "Mr. & Mrs. Smith" with Brad Pitt. In 2004, Jolie played the controversial role of Colin Farrell's mother in the movie "Alexander", which was all togas and draping fabrics. Obviously, it inspired her Academy Awards look that year.
Angelina looks like the queen of the carpet, and even without the neckless (that is stunning in our opinion), her dazzling looks would have done the dress justice. Even the tattoo on her upper arm gives a touch of rust to the over-cleaned look and shows Angelina in a sort of dimming light. We like!
Halle Berry, 2002
Not only did Halle Berry make history at the 2002 Oscars by being the first black woman to win Best Actress in the Award Show's history, but her iconic dress made history, too. This burgundy dress by Ellie Saab boasts a sheer bodice laced with embroidered flowers and a low-waist layered skirt.
As of 2023, Berry's dress now hangs in the Academy Museum of Motion Pictures. It stands among iconic outfits and costumes such as Dorothy's red slipper from "The Wizard of Oz," a $17 million Rolex watch worn by Paul Newman, and Shirley Temple's silver tiara from the film "Little Miss Broadway."
Michelle Yeoh, 2021
Yeoh starred alongside Pierce Brosnan in the 1997 Bond film, "Tomorrow Never Dies," and attended the franchise's "No Time to Die" premiere in 2021, proving she's still got it. Yeoh is no stranger to an Elie Saab number, and it's no wonder why. This is what aging with grace looks like, people!
This grey-toned powder blue dress, complete with a dramatic sheer shawl, looked like it was made for Yeoh. The Malaysian actress attended the London premiere solo. Or, at least, she might as well have. Even if she did bring a date, we don't think anyone would have noticed with all eyes on Yeoh.
Lady Gaga, 2009
What can one say about Lady Gaga that hasn't already been said? Over the years, the trailblazing star has worn nearly every outlandish look imaginable and made it work. Still, who can forget her fabulous black ensemble at the 2009 VMAs? The star wore a black lace Jean Paul Gaultier dress with a Dragon print silk underlay from Gaultier's fall/winter collection.
Gaga completed the look with a neck brace and mask by Keko Hainswheeler. She was also accompanied by Kermit the Frog. The star still constantly works and creates new music and new movies, so we haven't heard the last from her yet.
Katy Perry, 2014
Seeing Justin Timberlake and Britney Spears walk the red carpet in head-to-toe denim seemed like something we would see just once in a lifetime. Oh, how wrong we were! A little over a decade after that denim explosion, Katy Perry and rapper Riff Raff graced the VMAs with their version of the Canadian tuxedo.
Adding a bit more bling (okay, a lot more bling), Katy and Riff Raff paid homage to one of the most memorable red carpet outfits. We don’t know if it’s due to her vintage hair and makeup, but Katy actually rocked that dress! Unfortunately, we can't say the same for Riff Raff.
Rose McGowan, 1998
You know your outfit is outrageous when you manage to outshine shock rocker Marilyn Manson dressed in a head-to-toe leopard print suit. In 1998, Rose McGowan managed to make jaws drop when she showed up on the red carpet wearing a leopard print pair of underwear and not much else.
Wearing just a sheer beaded “dress,” it’s easy to see how Rose helped launch the “less is more” trend when it comes to red carpet fashion. According to the "Charmed" actress, the Maja Hanson dress was more of a “political statement” rather than a fashion statement. Well, we're not sure what political policies changed because of this dress, but A for effort, we guess.
Bjork, 2001
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 many years 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 30 years and many of her songs have been vital components of some of the most iconic movies and TV shows in recent memory.
Nicole Kidman, 2017
Nicole Kidman was a vision in her signature color — red — at the 2017 Emmy Awards. Her style team opted for a red silk gown by Calvin Klein that hit just above the ankles to show off her strappy pink heels by the same designer. No matter how Kidman ages, she always glows and walks with confidence on the red carpet.
Kidman kept the jewelry simple, which ensured that the dress got the attention it deserved. And the ultimate accessory for this look? Those two Emmys she picked up that night because she's clearly not just a pretty face. Her husband, Keith Urban, didn't hurt, either.
Emily Ratajkowski, 2017
The yellow gown trend was in full swing at the 74th Golden Globes After Party, with many stars wearing the bold hue, but Emily Ratajkowski stole the show that evening. The supermodel and actor showed off her killer legs in a stunning silky yellow Reem Acra gown that had jaws dropping left and right.
The daring dress featured a provocative slit up the middle and a bedazzled collar down her chest. However, things took an unexpected turn when she flashed an undergarment while playing with the gown's dramatic slit. The wardrobe malfunction didn't faze her one bit, however. The model partied the night away and looked fabulous while doing it.
Kylie Jenner, 2017
Kylie Jenner slayed the Golden Globes after-party scene with a dress that screamed Kim Kardashian! The youngest member of the Kardashian-Jenner clan strutted her stuff in a long-sleeved, off-the-shoulder silver gown adorned with a chunky choker and a thigh-high slit that could make even the most confident of us blush.
Remember when Kim wore a nearly identical gown to the 2016 Met Ball? The bespoke beauty was crafted by the illustrious design house, Labourjoisie. Kylie's date for the night was none other than her supermodel sis, Kendall, making it a true sister-sister fashion moment. With this kind of fashion game, it's no wonder the Kardashian-Jenner clan is always the talk of the town.