When it comes to awards in the entertainment industry, it’s the Oscars that gets most of the hype. But, any die-hard pop culture fanatic knows that for the past 36 years, the MTV Video Music Awards is the one awards show that cannot be missed. Not only has it delivered some of the best performances of all time (from Britney Spears to Madonna) and been the setting for iconic feuds (ahem, Taylor Swift versus Kanye West), but the fashion of all fashion moments frequently occur on the red carpet and during on-stage performances. While you may be wondering, last year’s 2019 awards show was the last “normal” red carpet we’ll see for a while, the truth is, only time will tell. , But that doesn’t mean we can’t pay homage to several of the most iconic outfits and memorable moments that shook us in years past. Put your seatbelts on, because we’re about to travel back in time to see the wildest, raunchiest, and most Avante Garde moments in the history of the MTV Video Music Awards.
WHO: Madonna . WHAT: ‘80s wedding dress and “boy toy” belt. One could say the very marriage of music and fashion at the MTV Video Music Awards began at their inaugural event back in 1984. Courtesy of Madonna, of course. Her performance of Like a Virgin in an ‘80s wedding dress with a “boy toy” belt kicked off the avant-garde style, and performances that became peak VMA materials and inspired performances and red carpet looks thereafter.
WHO: CherWHAT: Beaded leotard, long black coat. Cher has never been one to shy away from serving an iconic look—after all, who could forget her Met Gala look from 1974? And her ensemble for the ‘87 MTV Video Music Awards was no different.
WHO: Christina Applegate, Brad Pitt WHAT: On Christina: Floral a-line dress and matching scarf. On Brad: Black Blazer, Floral Vest; and a T-Shirt. Oh, how could we forget this moment from the 1989 MTV VMAs? I’m still not over this relationship—or these looks for that matter. I mean Pitt’s blazer and floral best situation? Peak ‘90s fashion. And Applegate’s sweet a-line floral dress and matching scarf are too sweet. They may have not lasted, but these looks still have my heart.
WHO: Madonna WHAT: Victorian gown, and fan. Let’s be real: Madonna has single-handedly given some of the best MTV Video Music Award show performances. Who could forget her performance of Like a Virgin in an ‘80s wedding dress at the inaugural show? Or when she stunned audiences by kissing Britney Spears and Christina Aguilera on stage in 2003? But the look (and performance) that definitely deserves some real estate in your brain is her Victorian-inspired ensemble for her performance of Vogue, at the 1990s show. The fan? Everything.
WHO: Cindy Crawford WHAT: Versace dress. Before Bella and Gigi Hadid were the best-dressed attendees of the 2019 awards show, there were the supermodels of the ‘90s; specifically Cindy Crawford. Who would ever want to forget this leather and sheer Versace dress? Not me, fam, not me.
WHO: TLC. WHAT: Matching head-to-toe white looks. It’s not a roundup of quintessential MTV VMA looks if we don’t speak to the power of the girl band with matching ensembles. And while getting matchy-matchy on the red carpet was king in the ‘90s and early 2000s; no other look is still as relevant as TLC’s 1995 MTV VMAs ensemble. With baggy pants, bare midriff, and chunky boots; this is a look we still see popping off on the gram today—and as far as the video they took four nominations home for that year, the song, Waterfalls is still a classic.
WHO: Mariah Carey . WHAT: Bandeau top, and black slit skirt. The year is 1997, and the radio is bumping, Mariah Carey’s most recently released album, Butterfly. So it makes sense that she was invited to the MTV Video Music Awards to present LL Cool J with his Video Vanguard award. But really, what makes this moment stick is Carey’s very on-brand, very ‘90s sleek two-piece number.
WHO Gwen Stefani . WHAT: Baby blue furry bikini top, futuristic skirt over black pants, and platform sandals. For better or for worse, the MTV VMAs have always served up some of the most controversial looks—including, Gwen Stefani’s 1998 look. There are so many things that make this look from Stefani both iconic and questionable; like the futuristic skirt over the pants are so ‘90s, but the Bindi Crystals are problematic. No matter your thoughts or feeling about this look, I’m thinking the furry blue bikini top with matching hair may be something we need to bring back.
WHO: Prince WEAR: Head-to-toe electric blue outfit. There are some years of the MTV VMAs that take the word iconic to a whole new level; the 1999 awards show was one of them. Not only did Prince serve up this iconic head-to-toe blue metallic look with hoops and matching braids. But, when the network asked him to perform his song, 1999, he rebuked and agreed to introduce TLC onto the stage. Basically, Prince was always willing to take a risk—which is why his legacy is woven into the fabric of the cultural zeitgeist.
WHO: Lil Kim WHAT: Custom purple jumpsuit with matching pasty. It’s not a list of icons (or iconic looks for that matter) if the mother of rap, Lil Kim isn’t on it. Not only did she pave the way for some of our favorite female rappers of this generation, but she served one of the most talked-about, most remembered looks probably in the history of the MTV VMA’s back in 1999. Kim’s custom jumpsuit by her stylist, Misa Hylton, not only attracted the attention of Diana Ross, but it ushered in a new wave of all-but-naked red carpet that still has the world-shaking.
WHO: Jennifer Lopez . WHAT: Sean John crop top and jeans. Jennifer Lopez knows a thing or two about putting together an ensemble that’s bound to go viral—and while there are a plethora of looks that can be recalled, maybe one of her most famous MTV VMA looks is the one she chose to wear to the 2000s award ceremony with her partner at the time, Diddy. She may not wear Sean John anymore—or date him for that matter —but twenty years later, her abs are pretty much the same.
WHO: Aaliyah WHAT: Roberto Cavalli gown. Before the beloved R&B singer, Aaliyah left us, she shared a few parting gifts. This includes her attendance at the 2000 MTV VMAs where she not only won Best Female Video that year for “Try Again,” but also served an iconic final look in a head-to-toe yellow zebra dress designed by Roberto Cavalli.
WHO: Pink. WHAT: Fur coat, halter top, low-rise denim. Singer Pink’s debut appearance at the 2000 VMAs epitomized the 2000s grunge fashion trend. How could anyone forget the usage of that much hair gel? How many pink at-home box-dye kits were bought after this red carpet look? How did her pants stay on despite the fact there’s no waistband? I still have so many questions…
WHO: Britney Spears . WHAT: That snake, fam. Not to play favorites, but we all know that if we’re ranking some of the most iconic MTV Video Music Award performances, no list is complete without the one-and-only Britney Spears. The moment she slithered onto the stage with a python to perform I’m a Slave 4 U, she solidified her spot in the VMA history books. Don’t believe us? Rewatch her performance for yourself.
WHO: Shakira . WHAT: Feather crop top, leather cowboy chaps. While Shakira’s performance with fellow pop star Jennifer Lopez for the 2019 Superbowl may be the only look you can’t get out of your head; I’m here to remind you, she’s always been one to serve a look whenever, and wherever. The proof is what she chose to wear to her MTV VMA debut in 2001—the cowboy pants, leather pants, and feather crop top are only a look that she could pull off.
WHO: Destiny’s Child . WHAT: Matching coral outfits with turquoise jewelry. Ah, who could forget the head-to-toe coral matching ensembles Beyoncé, Kelly Roland, and Michelle Williams wore to the 2001 MTV Video Music Awards? If you could survive wearing coral in the early ‘2000s, you can survive anything.
WHO: Christina AguileraWHAT: Baker boy hat, halter top, mini-skirt, knee-high boots. Only Christina Aguilera could pull off both presenting the Best Male Video to Eminem (despite their long-running feud), and this much midriff with the utmost grace.
WHO: Rihanna. WHAT: White low-rise jeans, a crop top, and a bedazzled vest. It’s crazy to think that Rihanna was only seventeen when she emerged on the MTV VMA red carpet in 2005 in quintessential mid-2000s look; and since then, has pretty much ruled every red carpet thereafter. As a vested RiRi fan, being able to witness the evolution of Rihanna’s career and style is something I’d replay forever.
WHO: Lady Gaga . WHAT: Alexander McQueen lace dress. No matter the year, no matter the show, Lady Gaga always brings it. Gaga’s beauty moments, personal style, and red carpet looks have always been regarded as show-stopping. After all, who could forget the meat dress she wore to the 2010 MTV VMAs? And while Gaga’s delicatessen-derived dress may be one of the earliest ensembles seared into the collective conscious, it should be known that Gaga was serving up shocking looks well before then Her multiple ensembles for 2009 MTV VMAs (like this full-body, red lace Alexander McQueen dress) are a prime example of Gaga’s ability to create a look rooted in the cultural zeitgeist for years to come.
WHO: Taylor Swift WHAT: Kaufman Franco gown. Possibly one of the most famous moments in awards shows history (and definitely in the history of the MTV VMAs) was when Kanye West interrupted Taylor Swift’s acceptance speech for Best Female Video of 2009. Taylor, of course, handled the situation with grace in a Kaufman Franco gown, performed live after the incident, and even got back her moment later in the show when Beyoncé invited her onstage to finish her acceptance speech.
WHO: Lady Gaga . WHAT: The meat dress. I’ll double down on stating the obvious that Lady Gaga has, and always will bring her a-game to the red carpet. We just have to take another moment to respect the flank steak dress designed by Franc Fernandez—because, when we talk about things forever seared into our minds, it’s this look she wore to the 2010 MTV VMAs. And while we know for a fact this dress has gone down in history as one of the most iconic VMA looks (as the dress is housed at the Rock and Roll Hall of Fame and Museum) the only question I still have is what exactly she put inside the meat clutch.
WHO: Beyoncé . WHAT: Dolce & Gabbana Purple sequin suit. As a member of the Beyhive, I must fully admit that the majority of Beyoncé’s looks and performances are forever ingrained into my mind. I spent copious hours debating whether her leotard look from her performance of Single Ladies (Put a Ring On It) at the 2009 VMAs or the moment she won her video vanguard award in 2014 deserved a spot on this list. But frankly, her perfect performance at the 2011 MTV Video Music Awards is well historic. Not only did she nail every single note in this stunning Dolce & Gabbana sequin suit, but at the end of her performance, she unbuttoned her blazer to reveal she was pregnant with her first child, Blue Carter Ivy—talk about a moment.
WHO: Selena Gomez, Taylor Swift . WHAT: On Selena: Atelier Versace dress, and Schutz Shoes; On Taylor: Hervé Léger By Max Azria gown. The 2013 MTV VMA show was one for the books; at least for former Disney stars like Selena Gomez and Miley Cyrus. While Cyrus’s infamous onstage performance went viral, the attention should have also been on that year’s winner of Best Pop Video, Selena Gomez. Not only did she take away an award for her sexier video, Come & Get It, but previous to the stars more youthful style choices; she wore a Versace gown with a bustier detail and high slit. Basically, this year was the stars embracing new looks that would alter the courses of their careers and pop culture itself.
WHO: Katy PerryWHAT: Atelier Versace. We’re not the only ones who live for a Britney Spears red carpet moment. In an homage to Spears and Justin Timberlake’s red carpet look for the American Music Awards in 2001, Katy Perry wore this head-to-toe denim Atelier Versace gown to the 2014 MTV Video Music Awards, giving the look a reboot in pop culture’s collective memory. If you’ve ever wondered how to wear head-to-toe denim, this is how you do it.
WHO: Nicki Minaj WHAT: Labourjoisie gown. Nicki Minaj has her fair share of iconic style moments—but what makes her stunning 2015 MTV VMA head-to-toe gold look so much different is the birth of the phrase, “What’s good, Miley?”. If we were to take a time machine back to 2015, Minaj’s Anaconda was nominated (and won) Best Hip Hop Video. When Minaj voiced her frustration around the lack of body diversity in other categories like Video of the Year, fellow artist Miley Cyrus commented back in the press leading to Minaj’s iconic call-out on-stage the MTV VMA stage. While we may all remember her speech, the moment should also be remembered for what it truly was; a call to celebrate the beauty of all bodies, especially if they’re in a Labourjoisie gown.
WHO: Miley Cyrus WHAT: Atelier Versace. When it comes to throwing a curveball (or a wrecking one) we thought we saw it all after Miley Cyrus’s controversial 2013 MTV VMA performance with Robin Thick and a foam finger; but alas, she wouldn’t stop serving looks. With eleven outfit changes in total, all styled by Simone Harouche, the 2015 show host, made sure her suspenders and seriously outrageous style were center stage.
WHO: Beyoncé, Blue Ivy. WHAT: On Beyoncé: Francesco Scognamiglio dress and Lorraine Schwartz jewelry. On Blue Ivy Carter: Lorraine Schwartz tiara; Mischka Aoki Grand Royalle Dress; Giuseppe Zanotti Dolly Sneakers. The thing I love about the MTV Video Music Awards is that you get to see a lot of full-circle moments; from the artist’s first red carpet moment to winning their own vanguard. But one full-circle MTV VMA moment that’s forever seared in my mind, is when Beyoncé brought her daughter, Blue Ivy Carter, in her little $11,000 dress to the 2016 award ceremony. For Beyoncé to announce her pregnancy on stage back in 2011, and then bring Blue in the downright chicest ‘Lil number a few years later had many beehive members (myself included) clapping and crying over this momentous occasion.
WHO: Rihanna WHAT: Alexandre Vauthier haute couture collared gown with a grommet belt. It’s not a VMA show unless the relationships, both professional and romantic, are on display. For many fans, the confirmation of Rihanna and Drake’s relationship rumors met their end at the 2016 MTV Video Music Awards. Although the moment that Rihanna dodged Drake’s PDA after her acceptance of the Vanguard award went viral, the real attention grabber of the night should have been this haute couture look.
WHO: Cardi B WHAT: Nicolas Jebran dress; Lorraine Schwartz jewelry; Alexander Acosta shoes. 2018’s MTV VMAs was a moment to remember for Cardi B for various reasons; it was the artist’s first red-carpet post-pregnancy, and she came through drippin’ in a velvety Nicolas Jebran dress. Not only did the artist further prove she’s a major style icon, but she also made history when she won the awards for song of the summer and best new artist.
WHO: Lizzo, Lil Nas x. WHAT: On Lizzo: Marc Jacobs Prom Dress, and scünci hair accessory. On Lil Nas x: embroidered suit by Union Western Clothing, and Gladys Tamez hat. 2019’s MTV VMAs were filled with so many good looks, but if we’re being honest, only two stars stole the spotlight with their performances. As some of the best new-comers to the music industry, Lizzo and Lil Nas X brought their A-games with sequins, ruffles, and bedazzled things galore. Their looks are the types we always look forward to every VMA: a little outlandish, a little sparkly, and something to remember for years to come.
Next: 15 Photos That Prove the VMAs Were Wild in the ’00s