It is always fun to watch the MTV Video Music Awards since it never disappoints in terms of style. Fair enough, it is not quite as glamorous as the Cannes or the Met Gala. However, it has its own type of fearless fashion that will impress even the most stylish among us. How can we ever forget how Beyonce announced that she was pregnant in her orange Lanvin number? Lady Gaga also pulled off her meat dress stunt during a different year. As usual, Miley Cyrus and Nicki Minaj have no qualms showing us their wild sides either. There have been a lot of memorable outfits worn to this event, and it is high time for us to take another look at them. Are you ready to take a walk down memory lane?
The Most Iconic Outfits Ever Worn To The MTV VMAs
Jennifer Lopez 2004
In 2004, Jennifer Lopez showed up in Miami for the VMAs looking like a million bucks. The brown dress is gorgeous on its own, but we doubt that it would have worked on anyone else. We love the black hat, which added more personality to the outfit. Those dangling earrings also add more charm to the look!
Jennifer Lopez 2004
Kelly Clarkson 2005
The original American Idol winner showed off her back in this sexy number! Her entire outfit perfectly matches her golden locks, from the earrings to the necklace down to the dress. She kept it simple when it came to her makeup as well. All she needed was a smoky eye and she was good to go.
Kelly Clarkson 2005
Fergie 2005
It is no secret that Fergie is not one for subtle looks. She wore this bright yellow dress that was short up front and long at the back. The pop of green literally ties the whole look together! This wouldn’t have been the same without the ruffle details. She chose to keep her face neat by pulling her hair back.
Fergie 2005
Beyonce 2006
Was there a year in which Queen Bey did not dominate the VMAs? We don’t think so. Anyway, she was nothing short of dazzling in this outfit. This white number resembled an art piece more than it did a dress with those crystal details and metal accents. It hugged her figure to show off her incredible body.
Beyonce 2006
Jennifer Lopez 2006
JLo has never been one to shy away from daring outfits! In 2006, she sported this shimmery outfit that came with a headpiece. It lent her an air of mystery. She looked like a star, literally and figuratively. It hugged her body but still made her look classy. She paired the look with beige knee-high boots.
Jennifer Lopez 2006
Rihanna 2006
RiRi has come a long way! In 2006, she did not look like a bad girl. On the contrary, she looked like an angel. The singer wowed us all when she showed up on the red carpet in a small white dress with metallic accents. Her style has evolved a lot over the years, and we love seeing how far she has come.
Rihanna 2006
Christina Aguilera 2006
Here is Christina Aguilera channeling her inner Marilyn Monroe! She looked glamorous in this daring number. We love everything about it from the way it clung to her curves to her curls all to way to the low neckline. The bold red lip went on to tie the whole look together! She is simply stunning.
Christina Aguilera 2006
Rihanna 2007
In 2007, Rihanna went with this tight little gown. She looked pretty in pink! If she went for an angelic look the previous year, she looked just like a mermaid this time around. She wore her hair short and kept her accessories simple. We love the tiny detail of her black nails. As usual, she turned heads.
Rihanna 2007
Katy Perry 2008
Take a look at Katy Perry and her outfit to the 2008 MTV VMAs. She has never been one to go with the flow! The singer decided to spice things up by eschewing a dress and sporting this summery outfit instead. We dig the bustier and satin shorts. This look reminds us of pin-up girls of old!
Katy Perry 2008
Lady Gaga 2009
While everyone likes to go for sparkly short dresses, Lady Gaga decided to go against the norm. In 2009, she took to the red carpet in this black Jean Paul Gaultier number. Her accessories completed the look, of course. It would not have been the same without her gold half-mask and that feathery neck brace.
Lady Gaga 2009
Amber Rose 2009
It was no secret that Amber Rose has a killer body. During the 2009 VMAs, she wore this snake-print catsuit that brought all her curves to the spotlight. With her shaved head, you can see just how beautiful she really is. The photo shows her with Kanye West. This was the year he interrupted Taylor Swift!
Amber Rose 2009
Cassie 2009
In 2009, Cassie was another stunner on the red carpet. She wore a black and pink dress with a plunging neckline. We love how the girly dress contrasted with her more masculine side shave. To finish the look, she put on silver jewelry, blue peep-toe heels, and a yellow clutch. How is it possible to be so pretty?
Cassie 2009
Jennifer Lopez 2009
JLo walked down the red carpet in this nude baby doll dress by Louis Vuitton. It would have been a simple dress had it not been for the gold halter sleeves! She completed the ensemble by wearing black Louboutin heels and dangling earrings. She was the very image of sophistication and elegance that night.
Jennifer Lopez 2009
Katy Perry 2009
The California Girls singer decided to go for something more glamorous in 2009. She wore silver from head to toe in this piece by The Blonds. She accentuated the dress by going for a simple metallic eye look. With this, Katy Perry has shown us that she has no problems pulling off both costume and couture.
Katy Perry 2009
Leighton Meester 2009
Back in 2009, it was hard to find a more popular show than Gossip Girl. Actress Leighton Meester must have known that all eyes would be on her when she went to the VMAs that year. She was stunning in her silver and nude Christian Cota dress. We love the matching booties and silver earrings!
Leighton Meester 2009
Lady Gaga 2010
When we talk about memorable VMA looks, this is the one that instantly comes to mind. Lady Gaga made history when she wore a meat dress on the red carpet in 2010. Nicola Formichetti and Franc Fernandez. This was when she showed us that she was truly unlike anyone else in the industry. Iconic!
Lady Gaga 2010
Katy Perry 2010
By this point in time, it is clear that Katy Perry knows how to impress on the red carpet. This time, she sported a sheer dress by Marchesa dress. Even though it is a fairly simple piece, she decided to have some fun with her hair this time. Those blue, pink, and purple highlights definitely spiced things up.
Katy Perry 2010
Selena Gomez 2010
Aww, can you believe how young Selena Gomez looked in this photo? It goes without saying that she was just as pretty then as she is now. The silver gown would have been flashy enough on its own, but the bustier is what really steals the spotlight here. A small detail like that can make all the difference!
Selena Gomez 2010
Beyonce 2011
Has there been a moment in which Beyonce did not look gorgeous? Doubtful. In 2011, she wowed all of us by showing up in this orange dress by Lanvin. The side-swept ‘do and the dangling earrings made her look like the epitome of elegance! This was also how she let the world know of her pregnancy.
Beyonce 2011
Selena Gomez 2011
In 2011, Selena Gomez slayed it on the red carpet when she wore this lacy black dress. Julien Macdonald was behind this mullet dress, which was party in the front and business in the back. The young woman decided to accessorize it with touches of gold through her shoes, clutch, and bracelet. She is so elegant!
Selena Gomez 2011
Miley Cyrus 2011
On the other hand, her fellow Disney star Miley Cyrus showed up in a gray Roberto Cavalli gown. If you ask us, the gown was a rather mature choice of outfit for her. She went with light makeup, which shows off her pretty face. The Hannah Montana actress went with silver accessories to cap it off.
Miley Cyrus 2011
Katy Perry 2011
The singer wore a couple of different outfits to the VMAs in 2011 but let us focus on this one. How playful is this look? She wore her hair short and pink with a flower ornament. It clearly drew inspiration from traditional Asian dresses. She decided to play it up even more by bringing a parasol with her.
Katy Perry 2011
Nicki Minaj 2011
This rapper is another person to watch during awards season! You never know what she will wear next. In 2011, Nicki Minaj went with this playful getup. There are so many things going on here that we do not even know where to start! There an ice cream necklace, a metal dress, a surgical mask, and more.
Nicki Minaj 2011
Jessie J 2011
The Price Tag singer stole the show wearing white tights, a leg-boot, and a sparkly leotard. It would be a disservice not to mention her decorated crutches as well. We doubt that it was easy to dress up the walking equipment, but she did it. She had to use it after she fell off the stage and broke her leg.
Jessie J 2011
Alicia Keys 2012
Not only does Alicia Keys have an amazing voice, but she has a fantastic style as well. This was evident when she took this asymmetrical silver dress to the 2012 VMAs. She flipped her hair over to one side to go with it. We love her choice of geometric jewelry as well. She clearly knew what she was doing.
Alicia Keys 2012
Miley Cyrus 2012
During the 2012 VMAs, the former child star blew us all away with her outfit. She arrived at the red carpet in a tasteful gown by Emilio Pucci. We love the way her platinum blonde hair stuck up. It was a great choice that only added more dimension when paired with the plunging neckline of her black dress.
Miley Cyrus 2012
Rita Ora 2012
This was the year that Rita Ora appeared at the VMAs for the first time. The singer looked fantastic in a unique jumpsuit by Emilio Pucci. The sheer number accentuated her cleavage. Its intricate silver detailing is a work of art in and of itself as well! She stuck with the color scheme by wearing black heels.
Rita Ora 2012
Katy Perry 2012
In 2012, Katy Perry shocked all of us not by wearing a wild outfit but by keeping things subdued! It was quite different from all her previous VMA looks. At any rate, we adored this sophisticated full-length Elie Saab number. It was the first time she wore something more “normal,” but she still looked amazing.
Katy Perry 2012
Nicki Minaj 2012
Here is another unique yet jaw-dropping VMA look that we love! First of all, Nicki Minaj looked great with her yellow and pink curly bob tucked beneath her black cap. The pop of color went well with her black and red lace jumpsuit by Versace. As you can see, it did an amazing job of showing off her figure.
Nicki Minaj 2012
Amber Rose 2012
The world found out that Amber Rose had a baby on the way in 2012. In a tight lace dress, the model shared the good news with all of us. Even though she typically wears more daring outfits, we think that she made the right choice by going with this tasteful look for the red carpet.
Amber Rose 2012
Selena Gomez 2013
This pop star was gorgeous as usual in a dark gown by Atelier Versace. We love the detail provided by the sheer bustier. The dress showed off her slim figure and made her look like a princess. It was a fitting outfit for a winner! Later that night, Selena Gomez brought home the Moonman for the best pop video award.
Selena Gomez 2013
Katy Perry 2013
Katy Perry decided to return to her wilder ways in 2013. She was seen wearing a leopard Emanuel Ungaro number to the VMAs that year. There is a lot going on with this dress. You have the high split down there. There is also that high neckline, as well as the gold feather-like details across her chest.
Katy Perry 2013
Miley Cyrus 2013
In 2013, the singer opted for a different look. Before she gave her shocking performance that night, she first wowed us on the red carpet. We love the cheeky bejeweled two-piece by Dolce & Gabbana. She looked youthful and raring to have a good time! The mini buns made her look even more playful.
Miley Cyrus 2013
Rita Ora 2013
The Hot Right Now singer turned heads when she showed up on the red carpet in this impressive blue number. This Alexandre Vauthier dress is as flamboyant as it gets! She looked like a true diva with its tulle skirt, blue feathers, and Swarovski crystals. The V neck also added more drama to the ensemble.
Rita Ora 2013
Holland Roden 2013
How gorgeous is Holland Roden? She wore a Naeem Khan piece when she attended the 2013 MTV VMAs. It was a unique look that only the most beautiful people on the planet have a chance of pulling off. The ball skirt over cigarette pants made her look both feminine and masculine at the same time!
Holland Roden 2013
Ciara 2013
We also have Ciara, who decided to slip into this sexy sheer dress by Givenchy Couture. The feathered skirt, lace embroidery, and shimmering stones all worked together for a subtle but sophisticated look. It made for a strong contrast with her dark tresses. All in all, the result was a rather sultry look. We love it.
Ciara 2013
Gwen Stefani 2014
Does Gwen Stefani even age? We are starting to think that the answer to that question is no. She looked chic and youthful as she walked in wearing a black and pink ensemble by L.A.M.B. We love the way she styled her hair as well. It was simple, but it worked. We adore the detail of her black nails.
Gwen Stefani 2014
Miley Cyrus 2014
The former child star showed up at the 2014 MTV VMAs in a matching black leather top and pants. This outfit came from the Fall/Winter 2014-2015 Alexandre Vauthier collection. The black made for a great contrast with her blonde hair and fair skin. The holographic sandals gave the look a subtle pop of color.
Miley Cyrus 2014
Chanel Iman 2014
In 2014, Chanel Iman went for a fascinating dress when she attended the MTV VMAs. Together with Jourdan Dunn, she sported a leather woven number by Balmain. This was a great way to draw attention to her height. She wore black from head to toe. Her hoop earrings and high heels were also in that color.
Chanel Iman 2014
Victoria Justice 2014
Actress Victoria Justice dazzled the crowds when she showed up in a white top and black leather skirt. As we all know, black and white ensembles are easy to wear with anything. She proved to us that it will even look good with a neon yellow clutch! It was a fun piece that read #hashtag.
Victoria Justice 2014
Taylor Swift 2014
The Love Story singer showed off her long legs in this tiny blue romper. This piece is a part of the spring 2015 collection of Mary Katrantzou. All the letters on the garment intrigued the viewers and fans. We have not heard of anyone uncovering the secret message just yet. If you have, let us know!
Taylor Swift 2014
Jennifer Lopez 2014
In 2014, JLo made jaws drop and eyes pop when she showed off her amazing curves in this revealing dress at the VMAs. She was sizzling hot in this metallic number, but we did not expect anything less of the singer-actress. As if the cut-outs were not enough, the high slit let her show off even more skin.
Jennifer Lopez 2014
Kylie Jenner 2014
This was such a great look on Kylie Jenner. Can you believe how young she looks in this outfit? She went with a Gothic look with this flowy black dress. The deep part on the side added a dramatic flair to the ensemble. As usual, her lips were painted in mauve. This is simpler than her usual outfits, and we love it.
Kylie Jenner 2014
Kim Kardashian 2014
On the other hand, Kylie’s older sister preferred something more colorful. Kim wore a short dress with a stylish plunging neckline and checkered pattern to the 2014 VMAs. It would have made for a harsh look if she did not pair it with soft waves and a natural makeup style. The bohemian look suits her!
Kim Kardashian 2014
Ariana Grande 2014
This petite princess has come a long way from her days as a Nickelodeon star. In 2014, Ariana Grande heated things up when she wore a matching bustier and skirt from Moschino. She slipped on a pair of high boots to cap it off. Of course, she did not forget to pull her hair up in her signature high ponytail.
Ariana Grande 2014
Katy Perry 2014
For the second time in VMA history, Katy Perry wore a full-length gown in 2014. This denim Versace dress takes the cake for us! She was completely dazzling in this unique outfit. We love every single thing about this ensemble. She kept it classy with a blunt fringe, a bold lip, and blue nails. What a stunner.
Katy Perry 2014
Amber Rose 2014
In 2014, Amber Rose practically went without clothes when she attended the MTV VMAs. She left very little to the imagination. Take a look at the photo so that you can see what we mean by that. The model turned heads when she slipped on a “frock” made up of silver chain. What a bold and memorable move!
Amber Rose 2014
Taylor Swift 2015
The gorgeous Taylor Swift showed up at the red carpet in Ashish matching top and pants. The metallic ensemble was different from what she normally wore. On her feet, she has Christian Louboutin heels. This was a bold outfit that was nothing like she had worn before. We admire her all the more for it.
Taylor Swift 2015
Gigi Hadid 2015
We are starting to suspect that it is impossible for Gigi Hadid to look bad in anything. Anyway, she was a true stunner in this yellow piece by Emilia Wickstead. The mustard yellow ensemble is not going to look good on anyone, but she looked absolutely gorgeous in it. The backswept ‘do is amazing on her as well.
Gigi Hadid 2015
Amber Rose And Blac Chyna 2015
This might just be the most daring look anyone has ever pulled off at a huge awards ceremony. Black Chyna and Amber Rose showed us how you should deal with haters. They decided to use their critics’ words as armor instead! In this case, they turned it into outfits worthy of the red carpet. This is one of our favorite entries on the list.
Amber Rose And Blac Chyna 2015
Jeannie Mai 2015
You might not be a fan of her fashion sense, but we can’t deny that Jeannie Mai is a confident woman who wears whatever she wants. She had no issues wearing this colorful little number. The fruity number is definitely eye-catching. The little pouf adds a touch of character to this already playful ensemble.
Jeannie Mai 2015
Sereyah 2015
The Empire star was drop-dead gorgeous when she showed up in this shredded white dress. We love all the textures you can see in this photo! Her booties matched the ensemble too. It would have been messy if she did not pull up her hair into a tight little bun. She looked nothing short of perfect.
Sereyah 2015
Kat Graham 2015
Before we talk about that dress, let us talk about how perfect Kat Graham’s hair is in this photo. Those waves are as perfect as it gets. Most people shy away from the color orange, but she had no problems rocking this vivid ensemble. To tone it down a little, she decided to wear it with black boots.
Kat Graham 2015
Nicki Minaj 2015
There is no way we would have ever forgotten about this one! Nicki Minaj dazzled all of us when she showed up in this golden sheer dress by Versace. The singer completed the Cleopatra look with winged eyeliner. She was fab and fierce, which is also the perfect way to describe her performance that night.
Nicki Minaj 2015
FKA Twigs 2015
Even though FKA Twigs prefers to do things her own way, she knows how to look amazing on the red carpet. Just take a look at this photo of her from the 2015 VMAs. We love this bold black Atelier Versace dress. It gives us both boudoir and vintage vibes all in one. She was absolutely stunning in this dress.
FKA Twigs 2015
Kim Kardashian 2015
Who said that you can’t look chic when you are pregnant? Kim Kardashian has shown us that this was not the case at all! We love this safari-inspired full-length gown that she wore to the 2015 VMAs. The reality TV star completed the look by slicking back her hair and donning a bronzed makeup look.
Kim Kardashian 2015
Rita Ora 2015
A lot of celebrities have tried their hand at feathery dresses, but this one might be our favorite iteration. The bodice resembles a bodice more than it does a shirt, but this is not a problem whatsoever. Rita Ora has never been one for minimalism, but this black dress delivers the maximum possible impact anyway.
Rita Ora 2015
Beyonce 2016
It is always amazing to see what Bey is wearing at any given moment. This one was no exception to the rule. In 2016, Blue Ivy was her date to the VMAs. The singer wore a sheer number with a feathery collar. Not everyone could pull this off, but she did! As usual, she adorned her ears with dangling earrings.
Beyonce 2016
Stella Maxwell 2016
The gorgeous Stella Maxwell looked great in this red and yellow Moschino two-piece outfit. We love how groovy this ensemble is! It was already full of character, so she decided to style her hair in a simple way. It would have been too ostentatious if she did anything more than to gather it up in a high ponytail.
Stella Maxwell 2016
Nicki Minaj 2016
It has become a meme that someone needs to help Nicki Minaj walk during events because of her sky-high heels. In 2016, her look was a little more subdued than the ones that came before it. Despite this, she still dazzled when she showed up in a skintight blue gown with mesh paneling and cut-outs.
Nicki Minaj 2016
Ashley Graham 2016
We are glad that Ashley Graham has never let her fuller figure get in the way of her fashion style. We are sure that you would agree with us when we say that she looked gorgeous in this sheer little number. The mesh pattern lent the barely-there outfit even more drama. We also love her rumpled bob!
Ashley Graham 2016
Rita Ora 2016
If anyone could pull off this look, it was going to be Rita Ora. In 2016, she stepped onto the red carpet in a black sheer dress from Marc Jacob. For a touch of modesty, she slipped on a leather jacket as well! It was a daring look that needs a lot of personality to make it work. Luckily, she had that in spades.
Rita Ora 2016
Katy Perry 2017
In a complete surprise to no one, Katy Perry brought her A-game to the VMAs in 2017. She wore a tight white asymmetrical dress that drew attention to her décolletage. It was a dramatic look that fit her to a tee. We just love the fact that she likes to stay true to herself when choosing her red carpet looks!
Katy Perry, 2017
Nicki Minaj 2017
When Nicki Minaj attended the 2017 MTV VMAs, she did so in a pink latex ensemble. For your information, the getup was created by VEX Clothing. She also dyed her hair pink to go with it. If you ask us, what really ties the whole look together was the silver jewelry that she used to accessorize.
Nicki Minaj 2017
Kesha 2017
She might be famous for her raver outfits, but Kesha was pretty in pink in this gown as well. It turns out that the party girl can rock a tulle dress too! The singer looked just like a princess, and we can’t get enough of this. We love her in just about any outfit, but we want to see more gentle looks like this one.
Kesha 2017
Alessandra Ambrosio 2017
Most of us would only wear patterns in moderation. However, Alessandra Ambrosio was gorgeous enough not to care about the fashion rules. The Brazilian model was a sight for sore eyes in this collared minidress. The only skin that we can see came in the form of the slits in her lacey, crisscrossed boots.
Alessandra Ambrosio, 2017
Heidi Klum 2017
Can you believe that Heidi Klum was already 44 years old when she attended the 2017 MTV VMAs? She has never failed to impress no matter her age. It is clear that the TV personality was dressed to kill for this event. Her cleavage was on full display in this revealing floor-length gown with the keyhole detail.
Heidi Klum, 2017
Vanessa Hudgens 2017
This actress-singer has always been gorgeous, so we are not surprised that she was dazzling at the 2017 VMAs. We adore her red dress that came with the tulle detail. She could have worn this in a softer color but opted for a fierce red instead. The textured hair also gave it more of an edge. She looks so good!
Vanessa Hudgens, 2017
Amber Rose 2017
We might as well list down every single time that Amber Rose has appeared at the VMAs. A lot of people had been surprised by how different she looked in 2017. The model was hardly recognizable when she sported sultry makeup and a brown wig. Meanwhile, her black beaded gown accentuated her glorious physique.
Amber Rose, 2017
Mariah Carey, 1997
Mariah Carey’s two-piece “revenge” look was widely regarded as one of the most shocking dresses of the 90s, despite the fact that it may not seem particularly controversial now. Carey paired her top with a long black skirt that fell to her ankles but featured a high side slit that ran the length of the skirt all the way to her hip, revealing her long, toned leg that had garnered a lot of attention. She finished off her look with a pair of black heeled sandals that looked like they belonged in the 90s.
Mariah Carey, 1997
Rose McGowan, 1998
Rose McGowan’s barely-there naked dress, which was also dubbed one of the most controversial looks of the 1990s, was reportedly a protest against Harvey Weinstein. She claimed it was a statement she made after being sexually assaulted. “I’ve never worn something like that before or since,” the actress said of the dress. “That was a political statement. Of course, there was no Twitter at the time or Instagram, no way to speak for yourself.”
Rose McGowan, 1998
Lil’ Kim, 1999
Lil’ Kim’s mermaid-inspired purple jumpsuit, wig, and sequined pasty will go down in history as one of the most memorable MTV VMA red carpet looks. Lil’ Kim had no idea when she walked onto the MTV Music Video Awards red carpet in 1999 that her iconic purple jumpsuit would make even Diana Ross absolutely lose it.
Lil’ Kim, 1999
Pamela Anderson, 1999
Pamela Anderson went for a bold look at the MTV Video Music Awards in 1999. The actress wore a white corset with sparkly, embellished pants and an equally embellished belt, all of which was topped off with a pale pink feathered hat because, well, why not?
Pamela Anderson, 1999
Jennifer Lopez, 2000
Jennifer Lopez knows how to put together a look that will go viral—and while there are a plethora of looks that come to mind, perhaps one of her most famous MTV VMA looks is the one she wore to the 2000s award ceremony with her then-boyfriend, Diddy. She may no longer wear Sean John—or date him for that matter—but her abs haven’t changed much in twenty years.
Jennifer Lopez, 2000
Macy Gray, 2001
It was the dress that was seen all over the world. Macy Gray, who is known for her outlandish style and music, decided to turn her award show dress into a walking billboard. “That was totally Macy’s idea, I just had to execute it,” says Ambrose, the designer of Macy’s immortal dress. “Working with Macy Gray was so much fun because she was an anomaly,” Ambrose remembers.
Macy Gray, 2001
Fergie, 2006
Fergie wore a Dsquared customized shirt, a half-tie, Burberry short-shorts, and knee-high boots for her pre-show performance of “London Bridge.” She then switched to a Max Azria Atelier that was custom-made for her.
Fergie, 2006
Cher, 2010
One of the most well-known songs in history is “If I Could Turn Back Time.” However, everyone remembers Cher’s 1989 music video outfit in addition to the catchy tune. Cher returned to music in 2010, and with it, she brought the ’80s back to life with a Bob Mackie original design for the 2010 MTV Video Music Awards.
Cher, 2010
Amber Rose, 2018
If the MTV Video Music Awards have taught us anything, it’s to expect the unexpected, and this year was no exception. Amber Rose dressed up as a sultry red devil for the ceremony in New York City. On the red carpet, the 34-year-old flaunted her curves in a latex corset with matching boots and a whip. Amber revealed that part of her outfit was inspired by Madonna when asked about her look.
Amber Rose, 2018
Madonna, 1984
Thirty-five years ago, at New York’s Radio City Music Hall, a rising pop singer named Madonna Louise Ciccone opened the first-ever MTV Video Music Awards. While older generations may recall the exact moment they first saw Elvis twitch his pelvis on TV or the Beatles perform on Ed Sullivan, Madonna’s racy, underwear-flashing, floor-rolling “Like a Virgin” performance was the defining televised music moment for children of the 1980s
Madonna, 1984
Christina Applegate, 1989
At the 1989 MTV Video Music Awards, the actress looked fabulous in a silk driving scarf and matching floral frock. And yes, this was the night Christina famously ditched her evening date, Brad Pitt for another guy!
Christina Applegate, 1989
Kim Basinger, 1990
Greased Lightnin’! Kim Basinger, a 63-year-old actress, and former fashion model has been turning heads on the red carpet for decades with her bold pantsuits and stunning blonde hair. At the 1990 awards show, the Batman star went full Sandy in a black catsuit, studded leather jacket, and thick headband, finishing her look with a red lip and black pumps.
Kim Basinger, 1990
Cindy Crawford, 1992
The supermodels of the 1990s, specifically Cindy Crawford, were the best-dressed attendees of the 2019 awards show before Bella and Gigi Hadid. Who could possibly forget Versace’s leather and sheer dress?
Cindy Crawford, 1992
TLC, 1995
It wouldn’t be a roundup of classic MTV VMA looks without mentioning the power of the girl band in matching ensembles. While matching outfits on the red carpet were all the rage in the 1990s and early 2000s, no other look is as timeless as TLC’s 1995 MTV VMAs ensemble. With baggy pants, a bare midriff, and chunky boots, this is an influential look that we still see on the gram today—and the song Waterfalls, for which they received four nominations that year, is still a classic.
TLC, 1995
Gwen Stefani, 1998
For better or worse, the MTV Video Music Awards have always featured some of the most divisive looks, including Gwen Stefani’s look from 1998. There are so many elements that make Stefani’s look both iconic and controversial; the futuristic skirt over the pants is very ’90s, but the Bindi Crystals are problematic. Regardless of your feelings about the look, I believe the furry blue bikini top with matching hair is something we should bring back.
Gwen Stefani, 1998
Prince, 1999
The MTV Video Music Awards have some years that elevate the term “iconic” to new heights; one of them was the 1999 awards show. Prince not only wore this iconic head-to-toe blue metallic look with matching hoops and braids, but he also wore this iconic head-to-toe blue metallic look with matching braids. When the network asked him to perform his song, 1999, he rebuked them and agreed to introduce TLC to the stage instead. Prince, in short, was always willing to take a chance, which is why his legacy is ingrained in the cultural zeitgeist.
Prince, 1999
Aaliyah, 2000
Aaliyah, the beloved R&B singer, left us with a few parting gifts before she passed away. This includes her appearance at the 2000 MTV Video Music Awards, where she not only won Best Female Video for “Try Again,” but also wore a head-to-toe yellow zebra dress designed by Roberto Cavalli as her final look.
The 2000 MTV Video Music Awards
Pink, 2000
Pink’s debut appearance at the 2000 VMAs epitomized the grunge fashion trend of the decade. How could anyone forget how much hair gel was used? How many pink at-home box dye kits were purchased as a result of this red carpet appearance? Despite the lack of a waistband, how did her pants stay on? I still have a lot of questions…
Pink, 2000
Destiny’s Child, 2001
Who can forget Beyoncé, Kelly Roland, and Michelle Williams’ head-to-toe coral matching ensembles at the 2001 MTV Video Music Awards? You can survive anything if you could survive wearing coral in the early 2000s.
Destiny’s Child, 2001
Christina Aguilera, 2002
Oh, the 2000s had some wild red carpet moments, and Christina Aguilera’s MTV VMA look from 2002 fits the bill. Don’t get me wrong: the look is adorable and a classic VMA look in and of itself, but only Christina Aguilera could pull off both presenting the Best Male Video award to Eminem (despite their long-running feud) and this much midriff with grace.
Christina Aguilera, 2002