As our two previous articles on the matter have shown, the stars at the event are known for putting together the boldest looks. Here are some more outfits we missed the last couple of times. Enjoy!
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 continually defied tropes of what artists “should” be.
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!
Lenny Kravitz, 1993
Lenny Kravitz arrived on the scene in 1989 edgy and bold with a presence that demanded attention. If that was not enough, the rock & roll and funk artist was also endearing and sweet! What a force to be reckoned with. In addition to his musical abilities, Kravitz became famous for his distinctive style, which was pathbreaking for the time.
Kravitz was way ahead of the curve with this metallic futuristic look at the 1993 VMAs. The theme would become a fashion rage in the late 1990s and early 2000s, but Kravitz had already moved on from the jumpsuit.
The Spice Girls, 1997
The VMAs today have celebrities one-upping each other for the most Instagram-worthy and raunchiest looks. It was the same in the early days, minus social media. Except, there were some legendary shoe moments in addition to the outrageous clothes.
Our favorite 90's band added some much-needed girl power to the 1997 ceremony. Ginger, Sporty, Posh, Baby, and Scary Spice look true to form and name! But check out the girls in their glorious platform shoes, will you? Fabulous stuff!
Busta Rhymes, 1997
Busta Rhymes arrived at the 1997 Video Music Awards wearing a maxi-style kimono! Why? Because he’s Busta Rhymes! Few people know that the star designed the ensemble himself as part of his luxury fashion line, Bushi Sport. Rhymes was always audacious and unafraid to go far, far out — either with his music or style.
People are still talking about the red maxi shirt, pants, and jacket ensemble he designed for the 1997 VMAs. The rapper brought gender-neutral clothing to the table long before it was considered trendy or acceptable.
Jennifer Lopez, 2001
Jennifer Lopez wore a one-piece, high boots, and a sun hat to make this a head-turning look at the 2001 MTV Video Music Awards. Unlike her all-out glam looks from the previous years, the queen kept it relatively understated but still risqué in a breezy mini Cavalli.
She still manages to stand out on the red carpet. When you’re JLo, you cannot blend into the background, even if you try.
Kelly Osbourne, 2002
The Osbourne star played into the graphic tee trend of the 2000s with a top that read: "My Boyfriend Is Out of Town." She also rocked a crimped bob, yellow eyeshadow to match her tee, and red lips to go with her shirt again. Now if that doesn’t scream wild child, we don’t know what does!
But there's much more to Kelly Osbourne, as everyone knows. She is a triple-threat entertainer — singer, model, and fashion designer. Apart from her edgy fashion sense, Osbourne is also known for her thought-provoking debates on talk shows and reality television.
Avril Lavigne, 2002
The MTV Video Music Awards in 2002 were awash in Y2K-style low-rise jeans and bubblegum pink. Of course, we cannot discuss pop-punk without mentioning the genre's queen, Avril Lavigne. The "Sk8er Boi" singer's outfit at the 2002 VMAs was completely on-brand for her.
A tie and studded cuffs were punk-rocker staples at the time. Avril Lavigne wore a white tank top, camouflage print cargo pants, and her signature tie. Lavigne remains a force to be reckoned with in both music and fashion.
Jessica Simpson, 2003
If you thought Taylor Swift scripted fashion history in her white pantsuit at the 2012 VMAs, think again! Nine years before, Jessica Simpson had already rocked an all-white silk pantsuit on the VMA red carpet.
Simpson was the picture of sophistication and class in an Emporio Armani ensemble paired with understated silver accessories. Far from outrageous, the singer chose vintage glam to make a statement, and boy did it leave a lasting impression!
Ashley and Mary-Kate Olsen, 2003
Mary-Kate and Ashley Olsen's twinning looks have won us over since the beginning of their careers on "Full House." From adorable toddlers to fashion sensations, Mary-Kate and Ashley Olsen are among the savviest, most successful designers today. Among their most memorable fashion moments was at the 2003 VMAs.
The sisters were at the height of their boho-chic phase that year – from breezy silhouettes to chunky jewelry. It is safe to say they completely slayed the look, turning heads and winning hearts as they arrived at Radio City Music Hall in New York City.
Jay-Z and Beyoncé, 2004
The 2004 VMAs were memorable in more ways than just audacious fashion. The event marked Beyoncé and Jay Z's first appearance as a couple on the red carpet, wearing outfits that have since become VMA legends.
While Jay-Z created waves with his fedora and all-white suit, the spotlight was on queen Beyoncé, rocking her vintage blonde curls and gold co-ords. The singer won the award for Best Female Video for "Naughty Girl" that night. During her speech, she said, "What up, Jay?" finally confirming their romance.
Gwen Stefani, 2004
Gwen Stefani has a hella good style, and you can't deny it. Since her “No Doubt” days, Stefani has effortlessly combined punk with pretty, red lips with leotards, or platform sandals with bikini tops. The singer brought her A-game to the 2004 VMAs.
We can't think of anyone else who could look this stunning in a Louis Vuitton corset and pencil skirt. The punk rocker meets vintage glam aesthetic effectively stopped everyone in their tracks.
Jennifer Lopez, 2004
Jennifer Lopez wore a strapless dress in different shades of brown to the 2004 VMAs. We don't know if this was one of her best looks, but the outfit stood out, alright! How could it not with those draped panels, sequins, and bandage-style bodice?
As if the busy outfit wasn't enough, the star chose to accessorize the outfit with feathered slingbacks, a wide-brimmed hat, chandelier earrings, a loud purse, and bracelets on both wrists!
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 glittering 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!
Chloe Fineman, 2022
Chloe Fineman arrived at the MTV Video Music Awards wearing what we can only describe as a blanket. If only we looked half as good when rolling out of bed! The Saturday Night Live star walked the 2022 VMA black carpet in a silver and chrome padded dress by threeASFOUR. She elevated her look with holographic sandals and chrome nails.
Fineman's outfit is most likely an homage to the moon man — the award ceremony's trophy mascot. At least, we hope it is. The internet has compared her look to a sleeping bag, a duvet, or Lizzie McGuire's igloo dress.
Kamie Crawford, 2022
At the 2022 MTV Video Music Awards, celebrities shone in glittering, head-turning outfits on the red carpet. Kamie Crawford, SI Swimsuit model and MTV's "Catfish" host, was also in attendance, decked out in a full Barbiecore ensemble.
Crawford looked stunning in a textured pink Hanifa gown featuring an off-shoulder detail and a cut-out across the waist and back. Crawford revealed that when her stylist showed her this Hanifa dress, she knew she had found her perfect VMA look. Plus, Hanfia was the brainchild of Anifa Mvuemba, a Congolese designer from Crawford's hometown. It was a no-brainer.
Monet x Change, 2022
We can't get enough of Ms. Monet's avant-garde look at the 2022 VMAs. The eyeshadow in technicolor, the flush on her cheeks, the accessories! All of it adds up and comes together beautifully. She makes us believe in cloud hair and even gives us reasons to try it out ourselves.
Her flawless ensemble was arguably one of the best at the 2022 VMAs. We bet this outfit will continue giving makeup and fashion goals for years to come.
Hilary Duff, 2005
Hilary Duff has been a red-carpet regular since she was 13 when she won hearts on Disney's "Lizzie McGuire." Slowly but surely, her style transformed from girly to glam. Nowhere was her fashion evolution more evident than at the 2004 VMAs.
Hilary Duff looked like a dream in her sequins and fringe dress as she channeled the uber-chic, high-fashion flapper within. Duff was dating Joel Madden from Good Charlotte then, and this was the first time the couple appeared in public together and presented an award onstage.
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.
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!
Jonathan Van Ness, 2019
The MTV VMAs are a place to have fun with fashion and express yourself, and no one got that message more than television personality and hairdresser extraordinaire Jonathan Van Ness. The Queer Eye co-host paired an elegant black romper with an elaborately embroidered Atelier by Frang black cape that would make any Disney villain jealous.
Exuding confidence, Jonathan shows us that our favorite red carpet outfits are sometimes the least expected. We totally think his co-host and style expert, Tan France, would approve of this fun outfit.
PJ Harvey, 1995
English singer-songwriter PJ Harvey was known to use fashion as a way to make a statement, and there’s no better example of that than the look she wore to the 1995 MTV VMAs. Wearing bright light blue eyeshadow, clownish red lipstick, and over-the-top false eyelashes, PJ’s outlandish outfit is easily one of the event’s most memorable.
The often-provocative singer actually justified her makeup look by saying that she found the garish makeup look “extremely beautiful.” We would like to politely disagree.
We need someone to explain why, in the early-2000s, we insisted on wearing clothes that looked like they had already been destroyed. This “shipwrecked” trend resulted in outfits consisting of slivers of fabric hanging on for dear life as Ashanti’s “dress” shows.
Held together with just some shimmering ropes, the small pieces of pink fabric had no chance of staying in place if there was a strong gust of wind. That said, most of us wore similar dresses. Let's not kid ourselves; this was the prom dress of our early-2000s dreams!
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.
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.
Missy Elliott, 2003
Missy Elliott may be one of the most talented artists in music, but even she couldn’t manage to “Work It” with this awful golf-inspired getup. Adidas tracksuits are already on most stylists’ no-no lists, so the fact that Missy chose to wear one in lime green and plaid probably enraged fashion critics even more.
In case the outfit couldn’t get worse, she topped it with this plaid hat and a huge yellow pom-pom. Why, Missy? Let’s hope she sent this terrible outfit to the big golf course in the sky!
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!
Proving that she is actually a pop culture goddess, Cher strolled onto the red carpet wearing her famous sheer bodysuit from her iconic “If I Could Turn Back Time” music video. Though the video premiered in 1989, Cher looked equally amazing wearing an updated version of it in 2010!
While Cher’s Bob Mackie-designed jeweled bodystocking caused quite the commotion, she was easily outshined when she was joined on stage by Lady Gaga in a dress made out of actual meat! But the icon didn’t have any hard feelings about another style stealing the spotlight. In fact, she found it “hysterical”!
Kacey Musgraves, 2021
If you’ve ever wondered what McDonald's Grimace would look like after a glamorous makeover, look no further than Kacey Musgraves’ 2021 VMAs dress.
The country singer decided to put a designer spin on the purple cartoon character’s trademark look with this deep purple Valentino Haute Couture dress topped with an oversized furry hat. In case that wasn’t enough purple, she also wore matching purple eyeshadow. While Kacey seemed happy about her choice, we’re sure that the audience members sitting behind her were less than appreciative.
Lil Mama, 2007
Rapper/singer Lil Mama of “Lip Gloss” fame decided to get back in touch with her inner child (or rather — baby) with this infantile outfit she wore to the 2007 VMAs. We really have no idea why she decided to wear a puffy lilac satin dress with a matching baby bonnet.
To make things even stranger, she was photographed with a Swarovski crystal-encrusted pacifier which she actually proceeded to put in her mouth! While this outfit is a whole bunch of no, we do have to commend her on her sensible choice of shoe wear (an out-of-frame pair of bedazzled sneakers).
Amy Lee, 2003
In the early 2000s, Amy Lee brought a darker sound to the music industry as the lead vocalist of the rock band Evanescence. Though there’s no denying that Amy has an incredible set of pipes on her, her sense of style often left a lot to be desired.
In 2003 she wore this strange mismatched outfit to the MTV VMAs that left us all scratching our heads. Combining a gothic leather corset with a frilly skirt and those curls we all tried to make with a curling iron, Amy’s look hit a sour note with fashion critics!
David Lee Roth, 1984
Compared to the outrageous antics former lead singer of the iconic band Van Halen has gotten up to in his career as a rock star, this tropical-inspired suit is actually pretty tame. In 1984, David Lee Roth took the concept of being on “island time” a bit too seriously when he showed up to the VMAs in this Hawaiian shirt-meets-suit and comical sunglasses.
In case his tropical flower-filled suit wasn't enough, the former-Van Halen frontman ditched the shirt and chose to wear several Hawaiian leis instead.
Pants, who needs them? Apparently, pants were optional at the 2021 VMAs, according to singer Normani. The singer opted to go pants-less to the awards show by wearing just a cropped long-sleeve jacket and not much else.
Check out those giant oversized cuffs. How do you even find cufflinks for those? Looking beyond the cartoonishly oversized top, her bottom consisted of just a couple of pieces of fabric that extended just below her stomach.
Lady Gaga, 2010
When it comes to coming up with unforgettable VMAs 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 gorry getup!
Amber Rose, 2014
Just when we thought we would see the end of strings and chains doubling as “dresses,” Amber Rose proved us wrong with this. In 2014, Amber walked the red carpet in a dress that completely reminded us of Rose McGowan’s infamous sheer chainmail outfit from years before.
Surprisingly, despite being quite revealing, the dress actually covered more than Rose’s dress! Also surprising is that this is just one of many shocking outfits worn by celebrity Amber Rose.
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.
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.
MC Hammer, 1990
The 1980s and early ‘90s had some very questionable fashion moments, and one of the decade’s most regrettable trends has to have been harem pants — a style popularized by rapper and dancer MC Hammer. For the 1990 VMAs, the iconic rapper matched his metallic harem pants with a jacket missing significant chunks of fabric.
Though it seemed that the rapper thought “It’s All Good,” despite missing significant amounts of fabric, fashion critics thought otherwise! Looking back, how did this look ever catch on?
Britney Spears, 2002
From pop princess to leather diva, Britney Spears decided to shed her innocent image with this leather outfit complete with a matching hat. Though her tiny studded dress, gloves, and lace-up heels wouldn’t get a second look today, decades ago, this look was considered quite edgy — especially for Britney Spears.
While her bold look was controversial, the real focus was on her interaction with the late pop icon Michael Jackson. After calling him the “artist of the millennium,” the king of pop was confused by Spears’s praise and thought it was an award — awkward!
Nicki Minaj, 2012
Nicki Minaj’s VMAs outfits typically test the limits to which fabric can be stretched, and her 2012 Versace black lace bodysuit was no different. Rocking neon yellow hair, Nicki debuted this slinky lace bodysuit with the outline of a corset embroidered into it in neon red sequins.
Nicki topped her jeweled and figure-hugging jumpsuit with an oversized captain hat. Though it was surprisingly conservative (for Nicki!), her superfans (aka Barbz) loved this subtle and interestingly constructed outfit. With so much confidence and talent, it seems that Nicki can shine on the red carpet wearing just about anything!
Joanie Laurer “Chyna”, 2000
As a former professional wrestler, Joanie Laurer, aka Chyna, has worn her fair share of ridiculous costumes. Outside of the ring, you would imagine that she would have wanted to wear something couture rather than a costume, but you would be wrong.
For the 2000 VMAs, the late wrestler wore a red, white, and blue leather jumpsuit that looked like something she would have worn in a wrestling match. While we’re sure the fashion critics didn’t love her patriotic pleather costume, it was part of her signature look.
At first glance, this may look like just your run-of-the-mill VMA outfit with cool shades to match. However, on closer inspection, you'll discover that...yes, that is a snake wrapped around H.E.R.'s neck!
It's possible that the musician wanted to pay homage to the iconic snake moment that Brittney Spears created in her performance of "Slave 4 U" way back at the 2001 VMAs. On the other hand, it's more likely that H.E.R. has a penchant for potentially "Toxic" accessories.
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.
Remember LMFAO? The pop stars who provided the soundtrack to every party you attended in the early-2000s brought their signature colorful clothing to the red carpet of the 2011 VMAs. That year, band member RedFoo wore a white fringed animal print jacket and matching chaps.
In case that wasn’t bad enough, the singer paired his outrageous outfit with boxers with a hand-print. The only one who needed to stop was LMFAO with their terrible fashions. RedFoo wasn’t joking when he sang “I’m Sexy and I Know It,” otherwise, we can’t explain how he could be so confident wearing that.
Big Boi and Andre 3000, 2001
Outkast members Big Boi and Andre 3000 usually have an effortless cool that makes us look past their rather questionable wardrobe choices. In 2001, however, we couldn’t look away from their cartoonish couture. Looking at their outfits, we were left with many questions.
Why was Big Boi wearing pants made from thick pink fur, and what was up with Andre 3000’s orange overall onesie? The green fedora and thick, leather armpiece instantly bring us back to the terrible trends of the early 2000s… ugh.
In the early 2000s, Fergie was trying to establish a music career outside of being a member of the Black Eyed Peas. That said, this school-girl-inspired outfit was definitely not the outfit to show us she was a serious solo artist.
We can’t be the only ones confused by her old-fashioned businessman meets go-go dancer look. Unfortunately, Fergie seemed to stick to different versions of this look throughout that time, including wearing a provocative version of a Girls Scouts uniform in her “Fergalicious” music video.
As one of the biggest bands in metal music, we were surprised to see members of the band Slipknot dress up in tuxedos… That was until we took a look at what was going on above their ties. Perhaps they were planning to go to a Halloween-themed party after the event or were planning on working at a haunted house.
Either way, we can’t understand why they look like they stopped at a costume store on their way back from the tailor. We're also trying to ignore the KISS-knockoff mask worn by the singer on the right.
Perez Hilton, 2009
You would think that someone who makes a living commenting on other people’s looks would put a bit more effort into his outfit for the MTV VMAs ceremony. In 2009, celebrity gossip blogger Perez Hilton actually left his home in this strange outfit.
Perez combined neon yellow boots with an equally bright pair of pink shorts and a floral blazer (minus a shirt, of course). In case the outfit couldn’t get stranger, he accessorized with yellow body paint on his hands. Or was there toxic waste involved?
Kim Petras, 2021
Kim Petras is a German singer known for her controversial lyrics and even more risque choices in clothing. For the 2021 VMAs, Kim wore an ornately embroidered dress featuring crosses and other religious symbolism. Though that dress was show-stopping enough, Kim paired it with a black latex bodysuit and mask.
Referring to her unique dress as a combination between “the religious stuff and then the freaky stuff," the singer arrived at the awards ceremony in Paris Hilton’s pink convertible! Talk about an entrance!
The Hives, 2002
The Hives are a Swedish rock group that broke out onto the scene with hits like “Hate to Say I Told You So.” While that song may have been a hit, their coordinated outfits certainly weren't. In 2002, band members walked the red carpet wearing button-downs and pants, each with a letter of the brand name spelled out.
Unfortunately, their effort was of no use as few people can barely remember them, let alone their names. At least the band member who got to wear the letter “I” in the form of a tie can re-wear his outfit!
Howard Stern, 1992
Fans of Howard Stern love the shock jock radio show host for his funny and irreverent style of entertainment. They didn’t know, however, that his bizarre tastes extended to his choice of wardrobe. In 1992, Howard attended the MTV VMAs dressed as his alter-ego, a character named Fartman (seriously!).
If seeing Howard strut his stuff in a tight gold lamé bodysuit was bad enough, wait until you see the back of the costume! The host bared everything in what was one of the worst outfits in VMAs history — no butts about it!
Steven Tyler, 1987
Steven Tyler may have been the hottest thing in rock music during the late ‘80s, but there’s no excuse for this revealing red number. The rock legend bared his chest in this suspenders and matching patterned jacket outfit. While we’re willing to look past the revealing top, there is no reason for someone to wear such tight pants.
Steven’s patterned pants were practically painted-on, leaving very little to the imagination. We don’t know how he was able to walk in them! We hope that this style of pants never comes back into style.
Prince was a musical genius, but his outfit at the 1999 MTV VMAs had us singing the blues. Playing into the futuristic theme in fashion at the turn of the millennium, Prince paired this electric blue latex turtleneck with equally shocking tight blue pants.
Somehow, Prince managed to rock the outfit in the way that only he could. The only cringe-worthy part of the outfit is his (out-of-frame) belly chain with charms. Even a unique artist like Prince couldn’t successfully pull off this stomach accessory!
Let’s take a nostalgic trip back in time to the 2002 MTV VMAs, where B2K (remember them?) attended the awards show in matching suede and shredded outfits. As awful as these outfits are, we do have to commend the boys of B2K for really sticking to their decision to match under any circumstances — even if it looks like they lost a battle with a pair of fabric shears!
But don’t worry, all those scraps of fabric found a new life as headgear. We’re just happy to see coordinated boy band fashions be a thing of the past.
Jessie J, 2011
Singer Jessie J wasn’t going to let a little thing like a shattered ankle keep her from attending the 2011 MTV VMAs. Sporting crystal-covered crutches and a bedazzled walking boot, Jessie proved that she wasn’t going to let a devastating foot injury keep her from the red carpet.
Though she may have been smiling for the cameras, behind the scenes the singer’s foot injury was so severe that she actually needed to get a bone transplant in her foot. Yikes!
Busta Rhymes, 1999
We’re not sure if it was the impending fear of “Y2K” or what, but for some reason, we were obsessed with futuristic space-inspired clothing. Metallic tones, latex, and strange cutouts were all the rage. Artists often wore these outfits in space-themed music videos or even on the red carpet.
That’s why we’re not surprised that rapper Busta Rhymes decided to show off his fashion of the future with this yellow halter-top and pants set. While he must have thought his outfit choice was cutting-edge, we just think it looks uncomfortable.
Proving that she still has what it takes to turn heads on the red carpet, Ashanti wore this strappy number to the 2021 MTV VMAs. While fans were happy to see their favorite R&B singer back in the music scene, some were confused by her choice of dress.
With so many straps, buckles, and harnesses, we imagine that it must have taken ages for her to get dressed. We can’t imagine how difficult taking a bathroom break must have been! We hope that she had assistants on hand to help.
Jessica Simpson, 2005
Fashion in the early 2000s could be easily defined as the era of “let’s add as many accessories as possible” to any outfit. One of the best examples of an unnecessarily busy outfit was this french maid costume and shorts combo that Jessica Simpson wore for the 2005 MTV VMAs.
Walking the red carpet with ex-husband Nick Lachey, Jessica proudly showed off this backless ruffled mess. Today, most fashionistas would cringe at the collection of ruffles, lace, bows, belts, and statement jewelry. This was peak 2005 in all of its maximalist glory!
With such an extensive collection of body art already, we don’t understand why Pink decided to paint fake tattoos all over her body for the 2002 MTV VMAs. For the event, Pink walked the red carpet in this fringed green-and-black striped halter-neck dress.
Her most memorable accessory? The line of fake tattoos ran from her shoulder to her ankle. The early 2000s were certainly a confusing time for red-carpet fashion! While Pink still isn’t a darling of the fashion critics, we’re just happy the faux body art is a thing of the past.
Mel B, 2017
As one of the very important spices of the formidable and iconic 90's girl group "The Spice Girls," Mel B, aka Scary Spice, rocked up to the 2017 VMAs ready to make a statement.
One way to get a message across loud and clear is to let your clothes do the talking. That's what Mel B did, literally! Her glittery dress had the words "You Will Never Own Me" in a glittery rainbow style. Whoever has the confidence to wear such a statement piece on the red carpet is certainly not owned by anyone!
Katy Perry, 2011
We suppose you could say that Katy Perry was thinking "outside of the box" when putting this outfit together.
Surprisingly, this is not a student's art project nor a strange Halloween costume. It's actually a head-to-toe Christian Dior designer outfit! You have to have a lot of confidence to confidently pull off pink hair with a massive yellow cube as your headpiece. Props to Katy for doing so!
Carmen Electra, 1997
Carmen Electra certainly was bearing all in this barely-there ensemble. 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!
Machine Gun Kelly, 2020
Machine Gun Kelly, aka Colson Baker, has not only made a major career metamorphosis, but his fashion game has evolved as well!
Baker isn't one to shy away from traditionally feminine colors and accessories which makes him a trail "blazer" (ha ha fashion pun) in his own right. His 2020 VMA look showcased his fashion fearlessness when he donned a hot pink monochromatic suit featuring a turtle neck and pearl necklace.
Cindy Crawford, 1992
As the host of MTV’s House of Style, fans knew supermodel Cindy Crawford would bring her fashion A-game to the red carpet of the 1992 VMAs. Wearing a leather and lace bustier with plenty of straps and buckles, her look was pretty daring.
The strappy gown was part of Versace’s risqué collection aptly called Miss S&M. Short of bringing a whip to the red carpet, Cindy let her head-turning dress do the talking. The look was even worn by singer Dua Lipa at the 2022 Grammy Awards.
Macy Gray, 2001
Before social media, artists had to get creative when it came to promoting their new projects. And what better place to share what you’re working on than the VMAs? Singer Macy Gray decided to use her body as a walking billboard when she ironed letters that spelled out the words “MY NEW ALBUM DROPS SEPT. 18 2001” onto her dress.
In case that was too subtle, the back was emblazoned with the command, “BUY IT.” Geez, Macy, we get it! Unfortunately, her little PR arts and crafts projects didn’t really work, and the album flopped.
Pamela Anderson, 1999
Let’s be honest; subtlety is not a word in Pamela Anderson’s vocabulary. Like most things on the buxom blonde, Pamela also prefers her hats supersized. The centerfold applied the “bigger is better” to her headgear.
The Baywatch babe turned to celebrity milliner, hat designer Ivy Supersonic, to create the oversized pink hat she wore to the 1999 VMAs. Pamela paired the huge pink feathered hat with a skin-tight white corset, bedazzled sequin pants, and heavy eye makeup. With then-husband rocker Tommy Lee, her look epitomized the style of the late ‘90s.
Kim Kardashian, 2016
When it comes to deciding on what to wear, most celebrities turn to stylists or designers. Kim Kardashian, however, decided to turn to Twitter. After asking fans if she should wear a “dressy sexy look” or “casual chill” to the VMAs, Kim decided on this vintage John Galliano dress for the awards show.
Kim paired the short and sheer black dress with I-just-got-out-of-the-pool “wet” hair. Though we’re sure the reality star doesn’t want to look back on walking the red carpet with her estranged ex-husband Kanye West, this dress was definitely one to remember!
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. 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.
Pink has always done her own thing when it comes to music and when it comes to fashion. Still a VMAs newbie, Pink decided to try something new, or rather many new things, when it came to figuring out her red carpet style.
The singer combined a sequined halter top with dangerously low pants (we still have no idea how they stayed up). To finish her look, she rocked gravity-defying spiky pink hair and a coat that we really hope no animals had to die for to make. We definitely don’t think you should “Raise Your Glass” to this look!
Avril Lavigne and Kelly Osbourne, 2003
Though there was no shortage of hot pink and barely-there looks, the early 2000s also gave us tons of emo and punk-rock fashion. Featuring stripes, skulls, and an ungodly number of safety pins, this look became one of the most popular alternative styles thanks to stores like Hot Topic.
Looking at this picture of Avril Lavigne and Kelly Osbourne, we’re totally getting “mom, can you pick us up from the mall?” vibes. If their look seems familiar, it’s because we’re sure that at least one person in your high school class wore something similar.
Lil’ Kim, 1999
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.
Gwen Stefani, 1998
We’re not exactly sure when it happened, but at some point during the late ‘90s, raver fashion moved from the underground to the red carpet. At least that’s what we think happened, otherwise, we really can’t explain Gwen Stefani’s look.
We’ve heard of matching accessories to your outfit, but most people don’t typically match their hair color to their bra! And that’s just what’s going on above the belt. Let’s not even get into her weirdly futuristic shiny skirt over pants. We’re really glad this chapter in Gwen's lookbook is done!
Jared Leto, 2017
While women typically get credit for trying brave and bold styles on the red carpet, there are some fashionably adventurous men out there too! Looking like an Amish farmer-moonlighting-as-a-magician-for-kids-parties, the Thirty Seconds to Mars lead singer had all eyes on him as he flaunted his sequined Gucci cape.
VMA viewers couldn’t ignore the actor/singer in his glorious garment — especially since the shine from the sequins reflected the ceremony’s stage lights. We'll just call him Jared and the amazing technicolor dream coat after seeing this outfit!
Lizzo proves that fantastic fashion is for every figure! The singer loves getting creative, and even a bit cheeky with her red carpet looks. Her “siren” dress for the 2019 VMAs was no different. The “Truth Hurts'' singer wore a customized red sequin Moschino gown with the word “SIREN” written all over it in silver sequins.
She completed the look with a matching red feather boa and glamorous bouffant hairdo. Looking every bit like a sultry siren, Lizzo proved that you can wear red on the red carpet without fading into the background!
Kim Basinger, 1990
By the late ‘80s, Kim Basinger was considered one of the most desirable women in Hollywood, thanks to her many sultry film roles. Perhaps that's why she chose to dress up as post-makeover Sandy from Grease?
In 1990, the actress wore a skin-tight black catsuit topped with a heavy leather jacket and thick headband to present the "Best Dance Video" award at the VMAs. While we would honestly rock that leather jacket today, “We [definitely don’t] Go Together” with her thick workout-style headband!
At some point in fashion history, we decided to embrace the “shipwrecked” trend when it came to fashion — people actually paid money for clothing that looked like it had been destroyed. A perfect example of the distressed clothing trend was the toilet-paper-inspired look that the R&B girl group TLC wore to the 1995 VMAs.
A departure from the oversized and baggy ensembles that the group typically wore, Chilli, the late Lisa “Left Eye,” and T-Boz sported these mummy-like costumes for the award ceremony. While their song “Waterfalls” won several awards, their outfits certainly didn’t!
Katy Perry and Riff Raff, 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!
Christina Aguilera, 2002
The early 2000s was... Uhm...a strange time for fashion. Skirts were just inches long, we had a mild obsession with hats, and basically, anything could double as a shirt. Case in point — Christina Aguilera used a scarf to make what might be the world’s smallest top.
Following the success of her hit “Dirrty,” Christina took a break from wearing leather pants and bikinis to put this equally revealing outfit together. We still don’t know how the singer made it through the entire awards show without a wardrobe malfunction!
Lady Gaga, 2009
When it comes to VMAs 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 next. When accepting the award for "Best New Artist," 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”).
There are some red carpet looks that are so iconic they inspire the fashion of that decade. In 1984, Madonna made shockwaves around the world with her provocative performance.
In what might be one of the most unforgettable performances in music history, the singer writhed around on stage wearing an '80s-style wedding gown with a collection of rosaries around her neck. Decades later, artists are still paying homage to this infamous VMAs look.
Amber Rose, 2018
Meow! We don’t know if it was her time dating Kanye, but Amber Rose has become an expert on how to command attention on the red carpet. In 2018, she pushed the limits of appropriate red carpet wear with this bold get-up.
We’re not sure why the model and television personality chose to wear a red (and uncomfortable-looking if we might add) latex bodysuit complete with a cat mask and whip. Perhaps it was laundry day, and this was the only clean thing she had in her closet? Either way, her memorable catsuit caused quite a commotion!
Jennifer Lopez, 2000
Jennifer Lopez knows a thing or two about wearing memorable outfits. No one can forget the infamous green dress she wore at the 2000 Grammy Awards. But few can forget the coordinated all-white outfit she and her then-boyfriend Sean Combs wore to the MTV VMAs that same year.
Wearing her ex-boyfriend’s label bedazzled on her shirt (who can forget Sean John clothing?) and a matching bandana, J.Lo brought an iconic feminine touch to streetwear. Although Sean Combs is no longer on her arm, decades later, J. Lo is still rocking crop tops!
Destiny’s Child, 2001
What could be worse than one suede fringed dress? How about three? In 2001, R&B girl group Destiny’s Child went west with their matching suede and turquoise ensembles. We’re not sure if the fabric store had a sale on orange suede, but somehow, there was enough of this oddly colored fabric to create these three awful outfits.
While Beyoncé’s outfit wasn't the worst, we can’t imagine how heavy Kelly Rowland’s necklace was. We hope for the sake of their neck health that these Western-themed outfits are tucked deep in the back of their closets.
Lenny Kravitz, 2004
The MTV VMAs might have a more laid-back dress code compared to other awards shows, but there’s no excuse for going shirtless. Even Lenny Kravitz’s amazing abs couldn’t save this confusing look he wore to the 2004 VMAs.
We still don’t understand what he’s wearing across his shoulders — are they some sort of wings? Lenny may have an angelic voice, but this outfit was pure fashion hell. Let’s not even get into the long fringed collar and angel wings. It’s safe to say that we never want to see this outfit “Again.”
Nicki Minaj, 2011
When it comes to picking a specifically crazy VMAs outfit, Nicki Minaj gives us lots of choices. This outfit, however, looks like Nicki got attacked by the stuffed animal section of a toy store while she was getting dressed.
Nicki wore this Harajuku-inspired playful outfit to the 2011 VMAs, where she picked up the Best Hip Hop Video award for her song “Super Bass.” Though Barbz (her superfans) were happy for their favorite rapper, they were worried about the collection of stuffed animals she seemed to be dragging onstage with her.
Megan Fox, 2021
Despite not being a recording artist, Megan’s outfit, or lack thereof, was one of the biggest stories from the 2021 VMAs. Not only did Megan walk the red carpet with her fiancé, rapper-turned-punk-rocker Machine Gun Kelly, but the paparazzi couldn’t get enough pictures of the actress and her bold look.
Wearing a daringly sheer dress and wet-looking hair, Megan paired her revealing look with bedazzled underwear and strappy heels — a look that has cemented her place as one of the trendiest women in Hollywood. Her look was so eye-catching that few even noticed her beau’s sparkly red suit.
Beyoncé is easily one of the most exciting artists to see on the red carpet, but when she was joined by her adorable daughter Blue Ivy wearing coordinated sparkly outfits, members of the “BeyHive” almost lost their minds!
Wearing a shimmering tulle dress, Blue Ivy showed us she’s a young fashionista-in-training. Beyonce looked simply angelic in her feathered, winged dress with intricate beading. While this outfit would look costume-like on someone else, Queen Bey proves she can rock anything from feathered wings to elegant evening gowns.
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!
Britney Spears, 2001
Back in the early 2000s, Britney Spears was eagerly trying to break away from her bubblegum good girl image and embrace edgier fashion. When Britney showed up to the 2001 VMAs in this sheer number, fans thought she went “Crazy” and wondered where the rest of her outfit was!
While this lace dress wouldn’t get a second glance today, it caused quite a scandal at the time. Little did fans know that Britney’s wardrobe would get even more revealing during her now-infamous performance for “I’m a Slave 4 U”.
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.
Rita Ora, 2018
Keeping up with the sheer-dress trend, Rita Ora made us do a double-take when she walked the red carpet in a stunning Giuseppe Zanotti dress. Though Rita joked that she chose the revealing dress because of the weather, we can’t deny that this dress is simply a work of art.
Unique squiggly lines intricately embroidered onto the sheer fabric of the gown prevented the singer from having a wardrobe malfunction by discreetly covering certain areas. This dress is the best example of “if you’ve got it, flaunt it!”
Christina Aguilera, 2003
Pink feathers may look great on flamingoes, but they certainly have no place on the red carpet! In 2003, Christina Aguilara walked the VMAs red carpet wearing this feathered frock. We’re so distracted by the fuchsia feathers that we didn’t even notice her early 2000s-era pencil-thin eyebrows and frosted eyeshadow.
All we can say is that we feel bad for whoever had to sit next to her during the event. They probably had feathers tickling them throughout the whole show!
Paris Hilton, 2002
While we’re not exactly sure how much Paris Hilton’s 2000 VMAs outfit cost, we think she overpaid as she got only half a skirt and half a top! That said, most of us owned at least one of these uneven “shark-bite” hem skirts during this time.
With her matchy-matchy pastel pink outfit and tiny bag snug under her arm, Paris Hilton defined the fashion of the early 2000s. Wearing a tiny halter top and an impossibly low-rise skirt (why was everything low-rise?), this outfit is actually pretty tame compared to other looks she was photographed in.
Shakira has always been one to embrace her own unique style and sound, even if it includes leather…like lots of leather…and even feathers. The Colombian singer attended the 2001 VMAs wearing lace-up and low-rise leather pants paired with a halter top made out of bird feathers.
On anyone else, we might think this is a fashion faux pas, but somehow she rocks it! While we like the sleek and chic look she sports today, we actually miss her cowgirl and leather style from when she released “Whenever, Wherever.”
We're not exactly sure, but somehow Eve managed to find a fur shawl that matched her hair color exactly. While most of her red-accented outfit blends into the red carpet, no one could miss her bright metallic gold dress.
The asymmetrical dress with the thick jeweled choker is surprisingly back in style today. With her signature short red hair and undeniable confidence, we’re sure no one was asking, “Who’s That Girl” when she stepped onto the red carpet!
Flavor Flav, 1990
We understand dressing for comfort, but rapper-turned-reality-star Flavor Flav took casual wear to the next level with his 1990 VMAs outfit. Flav wore his finest pajamas and slippers (!) to the event. If that wasn’t bizarre enough, he accessorized with a hot pink batman mask and his signature oversized clock around his neck.
Perhaps he was planning on sneaking in a few naps during the show? Either way, we applaud his dedication to dressing comfortably, even if it means looking silly.
Chloe Bailey, 2021
Chloe Bailey is one of the brightest young stars in Hollywood, but apparently, she needed to be more than just bright — she wanted to blind us. That's the only way we can explain this strange tin foil-inspired dress. Wearing what looks like an emergency space blanket, Chloe wore this silver Marni dress to the annual award show.
In case the dress itself wasn’t bad enough, you can zoom in and see that she’s wearing a chunky necklace with a picture of a spoon printed on it! It's not just you; we also have no idea what is going on here.
Avril Lavigne, 2021
Once a regular on MTV, Avril Lavigne has been missing from the music scene for several years, which is why we were so excited when we heard she would be attending the 2021 VMAs. That excitement quickly ended when we saw what she decided to wear. Hot pink plaid over a sparkly bra? Early 2000s Avril would never!
While her painful plaid outfit is giving us nightmares, we do have to appreciate how the jacket opens into a heart shape. Also good to see that she’s still rocking her signature over-the-top smokey eyeliner!
Paula Abdul, 1987
If you’ve ever wondered what a mermaid crossed with a country singer would look like, look no further. Paula Abdul showed up to the 1987 awards show looking like a mermaid that took a job singing at a local honky-tonk.
Wearing a turquoise sequined skirt suit and matching bra, she looked like Princess Ariel’s less-stylish cousin. We know we should cut her some slack, given that it was the late ‘80s, but we just can’t get past it. Between the sequins and the western-style fringe on the jacket, this whole look is “Straight Up” horrible!
Stacy Ferguson, 1998
Many people don’t know, but before Fergie was talking about her “Glamorous” life, the singer went by her real name, Stacy Ferguson, and was part of a girl's group called Wild Orchid.
In what must be the most late-’90s outfit we’ve seen in a while, Fergie showed up to the award show in this metallic monstrosity. Ignoring the awful metallic matching tube top and pants, why is she wearing a cowboy hat…and flip-flops? Did she plan on hitting the beach after the show?
Lil’ Kim, Mya, Christina Aguilera, Pink, 2001
Though this talented quartet may have won an award for their music video for the song “Lady Marmalade,” they certainly didn’t win over any fashion critics. Wearing what have to be some of the worst trends of the early 2000s, we wonder how they left their house looking the way they did.
From gravity-defying low-rise pants to unnecessary hats, we can’t believe so many fashion crimes could fit in one picture. Let’s not even talk about Lil Kim’s strange hair extensions. We like to think the girls were simply having a fashion “off day.”
Dennis Rodman, 1995
Known for his rather unique style, Dennis Rodman kept the tabloids busy during the ‘90s with his eccentric lifestyle and even stranger fashion sense. In 1995, the former NBA star put this interesting look together for that year’s VMAs.
While the top is actually pretty cute, we’re more concerned with what’s going on down below. Why was the top of his jeans made out of seersucker fabric? And what was with the belly chain? Either way, we’re happy Dennis got to explore his unique identity through fashion.