Here's a cool fact: While the Grammys awards musicians based on votes from members of the Recording Academy, the American Music Awards are voted on by the people who listen to music the most — the fans. With the 49th Annual AMAs set for Nov. 21, 2021, it's time to get pumped about all the winners, performances and — our favorite — the weird and wonderful fashion. Join Wonderwall.com as we take a look back at some of the biggest style moments at the AMAs through the years… starting with this newly free pop star… Just a few months after her hit MTV show "Newlyweds" premiered, Jessica Simpson hit the 2003 American Music Awards in this slinky pale peach number. The racy fitted dress was completely backless, showing off more than the previously pious singer was known to reveal on a red carpet. We liked seeing this new side of the then-new reality TV star. Extra points for matching her hair color to her dress!
Keep reading to see more memorable AMAs fashion over the years…
Back in 2000, nearly 20 years before the jumpsuit trend seemed to take over the red carpet, Britney Spears rocked this lilac-gray one-piece look on the American Music Awards red carpet. It featured a daringly low neckline bordered with glitter and was well ahead of its time back at the turn of the century.
We just can't with this high-ponytail-sassy-hand-on-the-waist look Ariana Grande rocked at the 2016 AMAs. Actually, we totally can. The singer opted for an I.D. Sarrieri belly-flaunting bustier and white straight-leg Alexander McQueen pants (kinda tuxedo-ish, right?) that had us chomping celery while doing crunches so we could copy the look.
The year was 1999, and *NSYNC members Justin Timberlake, JC Chasez, Lance Bass, Chris Kirkpatrick and Joey Fatone took home the prize for favorite pop/rock new artist. The boy band arrived at the show in some truly bold outerwear. While their turtlenecks and quarter-zip sweaters seem pretty standard for the time, it was their outrageous coats (and Lance's chunky double-breasted patent-leather suit) we can't seem to get over. Why did Justin opt for a metallic blue jumpsuit? Some things, we'll never know.
Justin strikes again! Jessica Biel, please forgive us, but we can't get over how ridiculously adorable Britney Spears and your husband, Justin Timberlake, looked at the 2001 AMAs. On one hand, their matching denim outfits are kinda hilarious, but on the other, they were the fashion moment of the year and, possibly, the decade. To this day, fans remember the moment JT and Britney stepped out wearing matching patchwork denim outfits only made snazzier by Justin's jean hat. This is a fashion faux pas that's never (ever) going away.
It's just a boring night at the 2013 AMAs with a very normal Lady Gaga riding in on a giant white horse. No big deal, right? WRONG. Forget about her totally gorgeous violet Versace gown, let's talk about her horse accessory. Gaga claimed she was inspired by the legend that Bianca Jagger once rode a white horse into Studio 54 in 1977. However, Bianca herself dispelled the myth in 2015 when she told the Financial Times that while she did get on a horse at the popular night club, she never rode it in, as it was "already there." Sorry to ruin your moment, Gaga!
Kanye West's first American Music Awards ensemble? It was actually pretty simple, if not woefully casual. The rapper picked a cheery jacket in primary colors, dark jeans and some sneakers for his debut AMAs red carpet back in 2008.
Here's the thing: Taylor Swift always gives good AMAs fashion, which is why this subdued jade green Michael Kors dress she wore the 2014 show was kind of shocking. The dress doesn't look bad on Tay's lithe frame and we're loving the tummy-baring cut-out, but what else is happening here? Honestly, a whole lot of nothing. It's the kind of gown that could pass as a mild-mannered award-show dress that doubles as a summer swimsuit cover.
Before we say anything about this champagne-hued Giorgio Armani dress, let us remind you that Selena Gomez was only 19 at the 2011 AMAs. More like 19 going on damn girl.
Madonna, who wore an off-the-shoulder gold minidress, took home the prize for favorite pop/rock female video artist at the 14th Annual AMAs in 1987. We're dead serious when we say that her eyebrows are totally welcome anytime. That crinkly dress, however, can stay in the '80s.
In 2001, it was totally cool to match outfits with the other members of your music group. At least Destiny's Child trio Kelly Rowland, Beyonce and Michelle Williams thought so. The ladies (who won the AMA for favorite R&B group that year) actually looked gorgeous in their body-hugging pink-and-white ensembles that featured different necklines and shapes to give each of the women their own individual style.
Post Malone plays by his own rules when it comes to style, and his 2018 American Music Awards ensemble was no exception. The music star arrived in this wild getup — complete with snake embellishments, a blinged-out belt buckle, matching bedazzled boots and a red Solo cup as an on-brand accessory. What a "Rock Star"!
Next up? Gwen Stefani's 2015 AMAs look: a sheer gown by Yousef Aljasmi. While some critics raved over Gwen's "daring" dress, we immediately thought the No Doubt frontwoman took too much inspiration from Batman. If we break it down in components, Gwen's rocking a lot of '60s platinum-blonde hair, yards upon yards of ill-fitting sheer black netting (which we guess could be turned into wings if she has to fight crime later in the night) and "Underneath It All" (see what we did there?), a gymnastics-friendly black leotard. Worn all together, the look didn't work for us, but the great news is, Gwen's the kind of star who makes her own fashion rules.
At the 1997 AMAs, Shania Twain looked like a sartorial goddess. The Canadian singer, who took home the award for favorite female country artist that year, opted for a black crop top with a high neckline and tapered copper trousers. Her look was simple but undeniably chic.
Cardi B served up some serious couture at the 2018 American Music Awards. The rapper wore head-to-toe Dolce&Gabbana in the form of this ultra-glam floral confection with thin straps and a full skirt and an equally standout matching headpiece.
What would an AMAs fashion list be without paying tribute to the bright light that was Whitney Houston? Seen here with singer Sheila E., who was rocking a very fetch purple-and-white suit (so Prince, right?), Whitney was all glorious big hair and smiles in 1986. Her slim black gown featured a shiny blue satin bow on the shoulder, accentuated with a cascade of silver beads. Whitney ended up taking home three of the seven awards she was nominated for while Sheila was there to support her friend in total '80s style.
Red-hot! Kelly Clarkson arrived at the 2004 AMAs wearing this gorgeous red corset-style dress featuring thin straps, a slinky silhouette and a train! She finished things off with a glam updo and looked every bit a music star.
She's come a long way, hasn't she? It's hard to believe, but yes, this is Beyonce. And yes, she really wore this hideous slinky gold mermaid-style gown to the 2007 American Music Awards. We're pretty sure that Queen Bey wouldn't be caught dead in this tacky getup nowadays, but over a decade ago, this questionable frock was the epitope of style.
Christina Aguilera brought all the va-va-voom to the 2013 AMAs in this sultry white Maria Lucia Hohan gown. The geometric cut-outs on the sides and thigh-high slit gave all the right attention to Christina's amazing figure. Funny story — she gave birth to her second child almost nine months exactly from this night…
We see you, J.Lo! Jennifer Lopez showed up to the 2020 American Music Awards in this gorgeous silver sequined set by Balmain. The two-piece look consisted of a cropped long-sleeved top with a plunging neckline and a slinky skirt with a thigh-high slit.
Beauty in burgundy! Kylie Jenner attended her second American Music Awards in 2014 in this showstopper of a dress. It featured spaghetti straps, a plunging neckline and a sky-high slit, and she brought an extra layer of funky with freshly dyed streaks of green in her hair.
Fun fact: Hilary Duff's "The Lizzie McGuire Movie" hit theaters just six months before this photo was taken! At the 2003 American Music Awards, the teen star wore a black tank top and a gold sequined miniskirt accentuated by black feathers along the hemline. She finished the look with slinky sandals and a statement necklace.
Time and time again, Pink has shown us that when it comes to award-show fashion, she doesn't mess around. This was especially apparent at the 2001 AMAs when she opted for this exposed bustier bra-and-overalls look. Pink, who was nominated for best soul/R&B new artist that year, even had her name written in metallic pink down her leg — a very on-brand detail at the time.
Demi Lovato looked positively beguiling in this black-and-gold Lorena Sarbu gown with a scalloped open back and thigh-high slit at the 2015 AMAs. The romantic look was further accentuated by their pin curls and wine-stained lips. It's so 1920s and we love it.
In 2019, Taylor Swift attended the American Music Awards in this sparkly green look that seemed to channel a minidress and floor-length gown at once. Tay paired the draped Julien Macdonald frock with over-the-knee boots by Casadei.
Mariah Carey's going to hate us for digging this one out of the archives. Back in 1992, the fresh-faced singer (who won the AMA for favorite female soul/R&B artist) chose a gold sequined minidress (which is actually pretty cute) that she hideously paired with shimmery pantyhose, and we just can't forgive that.
Who could forget this now-iconic sartorial moment? Selena Gomez attended the 2019 American Music Awards looking equal parts sweet and sultry in a lime green Versace minidress that she paired with matching pointed pumps.
At the 2019 American Music Awards, Halsey hit the red carpet in a truly unforgettable look. The "forget me too" singer wore a ruffled floral Marc Jacobs gown that brought all the drama. Complete with bold, matching eye makeup, bleached brows and statement hair, the chart-topper made a serious statement.
We love Kelly Clarkson, but we definitely did not love the rhinestone-studded gown by CD Greene that she wore during the 2009 AMAs. The sequins along the neckline oddly resembled a silvery Ms. Pac-Man chomping its way down the front.
Sizzling singer-actress Janelle Monae looked so fierce at the 2016 AMAs that she made us want to break the law and get handcuffed. Wearing a fetching black-and-white striped fur coat and minidress (courtesy of Marc Jacobs), Janelle had a whole "Bugsy's bad-a** wife who just broke out of prison" vibe working for her. We dig it.
We love a monochromatic moment! Alicia Keys attended the 2002 American Music Awards (where she won the awards for favorite new pop/rock artist and favorite new soul/R&B artist) in this all-black getup. She played with textures, opting for a sequined pantsuit and lace bustier top, and punctuated her look with a retro-inspired red fascinator.
Queen! Dua Lipa took us on vacation with her look at the 2020 American Music Awards. The "Future Nostalgia" pop star — who won for favorite pop/rock song for "Don't Start Now" that year — looked gorgeous in this minidress from Versace covered in starfish-shaped embellishments and a shell-inspired bust, all made even more feminine with dainty pink ruffles along the hemline.
Miley Cyrus is one of those gals who can wear haute couture or Target clearance and still come out on top. At the 2010 AMAs, she picked couture with this pink-and-white Marchesa mini that had a whole lot happening in the back. What you can't see from this picture is the giant billowing bow that connected that impossibly long train to her super-tiny, super-sexy dress. Instead of coming off as obnoxious, the short/long combo really worked and Miley had everyone doing a double-take.
Ashanti arrived at the 2003 American Music Awards looking like am early aughts vision in this figure-flattering pink-and-orange gown crafted from lace, beads and sequins. And you've gotta love that she carried a clutch that featured her own face.
The 1999 AMAs were good to The Chicks, who arrived in these adorable dresses. The trio, who took home the award for favorite new country artist, went with complementary looks — Emily Robison opted for a funky paisley-print frock, Natalie Maines wore a metallic silver get-up and Martie Maguire donned a strapless pink gown. That night, they performed their hit track "Wide Open Spaces."
Remember when the blazers-and-denim combo had a major moment? Jessica Alba attended the 2003 American Music Awards in a light blue blazer (with a sparkly top underneath) and jeans, which she paired with open-toe heels.
At the 2020 American Music Awards, model-actress Cara Delevingne posed for photos in a glamorous platinum pantsuit by Dolce&Gabbana. She opted for a sheer bustier top and elevated her look with pointy black pumps.
Could they be any cuter?! At the 1999 American Music Awards, twins Tia Mowry and Tamera Mowry looked dressed for the prom in their coordinating ballgowns. From the earthy tones to the oh-so-'90s silhouettes, these looks make us feel so nostalgic!
Can we get an amen? We're just going to get on our knees and thank Monse for designing this America-inspired sequined red, white and blue off-the-shoulder gown that actress Zoe Saldana wore to the 2016 AMAs. The mom of three didn't let an insane election season ruin her sense of patriotism (or fashion).
"It Wasn't Me" hitmaker Shaggy looked cool at the 2001 American Music Awards where he punctuated his otherwise all-black ensemble with this statement metallic green coat.
Aly & AJ were all the rage in 2006, but these dresses? Not so much! Pop-star sisters Aly Michalka and AJ Michalka showed up at the 2006 AMAs wearing these unfortunate dresses that looked like they came straight off the sale rack.
A year before she began starring as the titular teen on UPN's "Moesha," Brandy attended the 1995 American Music Awards looking on-trend in this metallic light blue blazer-and-shorts combo, which she paired with a sparkly top, tights and strappy silver heels.
Mya looked stunning at the 2003 American Music Awards. The singer, who's known for her tracks like "Ghetto Supastar (That Is What You Are)" and "Take Me There," opted for this colorful patchwork-inspired floor-length gown and finished the look with a statement flower in her hair.
Toni Braxton not only won big at the 1995 American Music Awards (she took home the honor for favorite soul/R&B album) — she looked like a total goddess too! The "Un-Break My Heart" singer wore a coordinating midriff-baring set that consisted of an asymmetrical long-sleeved top and a floor-length skirt with a dramatic slit.
As the host of the 2016 AMAs, model Gigi Hadid knew she had to bring her fashion A-game. She had several amazing looks that night but one of our favorites was her red carpet dress. This pure white lace, off-the-shoulder number from Roberto Cavalli had an edgy bridal thing going for it (the dress was completely sheer so even though it looks modest at first glance, it's actually quite revealing).
David Boreanaz, who in the late '90s and early aughts portrayed brooding vampire Angel in the "Buffy the Vampire Slayer" spinoff series "Angel," attended the 2001 American Music Awards in this peculiar getup. From the long animal-print coat to the burgundy button-up and leather pants, David's look was a fashion miss in our books.
Cute! "Desperate Housewives" star Eva Longoria showed up to the 2004 American Music Awards in a pale blue spaghetti-strap minidress embellished with rows of giant circle-shaped sequins and simple strappy metallic sandals.
We'd be offended if Nicki Minaj didn't wear something totally wild on the red carpet. She didn't disappoint at the 2010 AMAs in this Manish Arora dress and green-tipped hair. Nicki took the look straight off the runway and while it's busy, loud and a bit confusing, we're weirdly in love with it. Maybe it's her megawatt smile and total confidence that make us say "yes" when every fiber in our being knows we really should be saying "no, definitely not."
"Angel of Mine" hitmaker Monica attended the 1999 American Music Awards in this coordinating look, which was definitely on-trend at the time. She wore a metallic purple tank top with a silver floor-length skirt and finished the look with a pair of strappy sandals.
We're used to "Grown-ish" star Yara Shahidi really wowing us on the red carpet, so the 2017 AMAs were a monstrous disappointment. The stunning star arrived wearing Prada, but her mismatched ensemble let us down. From the trench coat over the black button-down to the zebra-print collar and those gray embroidered shorts, there was too much happening for our eyes. And don't even get us started on the knee socks and platform heels combo. Sorry, Yara!
What is this and why are we being forced to look at it? We'd never heard of Z Lala until we looked her up (after seeing this hideous dress), but found out she's an Armenian-American singer who can reportedly belt out tunes in 19 different languages. That's actually cool, but her style — not so much. We guess the dress (and the hair…) worked because now we know who she is and we're really sad she has such bad taste in fashion.
We know Jennifer Lopez is a triple threat in the entertainment world, but at the 2015 AMAs, she was a decuple (that's times 10) threat in her 10 very unique gowns. If you don't remember, Jenny from the block was the host for the night so her extravagant wardrobe changes aren't as extra as they might sound. We liked all her looks but this Aphrodite-inspired gown, which makes Jenny look like she's rising from the waves (or was it an open clam?) completely naked, glistening with sea mist is our fave because only she could pull this off and not bat a single eyelash.
Talk about taking the red carpet seriously! At the 2019 American Music Awards, Katherine Langford showed up in this show-stopping textured red gown by Rodarte. With her matching red eye makeup, studded gold accents in her hair and Stuart Weitzman sandals, her look was unforgettable.
At the 2020 American Music Awards, Taraji P. Henson impressed in this long-sleeved minidress by Armani Prive that was decked out in sparkly sequins and beautiful embellishments on the collar and sleeves. The real statement however, came with her delicately beaded headpiece!
Mary J. Blige got a lot of flack from fashion critics for her animal-print Roberto Cavalli gown at the 2011 AMAs. Not to beat a dead leopard (bad pun, to our knowledge no leopards died in the making of this awful dress), but the stretchy printed gown did a whole lot of nothing for Mary's amazing figure. It's paired with the wrong earrings and the wrong hairstyle and all together, it clashed on the musical goddess who is, in our eyes, still one of the baddest chicks in the game.
At the 1996 AMAs, Brandy took home the award for favorite soul/R&B new artist. In addition to winning big, the "Missing You" hitmaker looked chic in a metallic green pantsuit with matching pumps.
That's hot! Paris Hilton attended the 2008 AMAs in this slinky little gold number. It was a quintessentially late-'00s look, complete with her signature sideways pose.
At the 2010 AMAs, Rihanna stunned in this sheer red jewel-toned dress by Elie Saab. The gown featured intricate floral patterns on the bodice and a long, pleated skirt.
Young and rebellious singer Halsey had a futuristic vibe going at the 2016 AMAs. Rocking a skin-tight all-white Ermanno Scervino one-piece jumpsuit and a shaved head, Halsey was everything we ever wanted to be, even if we didn't know it until that moment.
This isn't the best look we've seen at the AMAs, but it is one that's definitely memorable. At the 2001 show, "Graduation (Friends Forever)" singer Vitamin C opted for a crop top featuring one of the most quintessentially '00s logos ever: the Playboy bunny (in glittery pink, no less).
At the 1995 American Music Awards, Queen Latifah made a bold statement in this monochromatic ensemble! The "Ladies First" hitmaker stepped out in a red leather suit that she paired with matching red heels.
Va-va-voom! Shakira wowed in Versace at the 2009 American Music Awards in a bright yellow minidress that came straight from the runway, pairing it with some seriously high platform heels.
Who doesn't love a good matching moment? At the 1998 American Music Awards, the guys of Boyz II Men all sported these coordinated dark blue suits, making for a very memorable fashion statement.
Katy Perry was definitely leaning on the edge of fashion at the 2011 AMAs in this strapless Vivienne Westwood gown. Separately, each of her fashion choices worked. The pink bouffant-y hair, the dramatic makeup with wing-tipped eyeliner and blood-red lips, the pink sequined gown with soft pleats and Japanese writing — and even the peep-toe blue heels she sported underneath. But together? It was a jumbled mix that failed to tell a cohesive fashion story.
Years ahead of the trend! Back at the 2008 AMAs, singer Natasha Bedingfield sported this chic all-white pantsuit sans shirt. All these years later, this menswear-inspired style remains all the rage!
We really loved this bronze Catherine Deane leather-bodice gown Pink wore to the 2012 AMAs. It has a sexy gladiator-meets-Carrie (from "Sex and the City" circa 2005) vibe that, when paired with her rockin' short hair, makes Pink look feminine and funky all at once.
Britney and Justin weren't the only ones rocking double denim at the 2001 American Music Awards! Rapper Sisqo, who had a huge hit with "The Thong Song" that year, also sported a Canadian tuxedo to the ceremony, adding a black graphic T-shirt underneath plus a long chain.
Christina Aguilera has experienced quite the sartorial evolution over the course of her career. In 2001, she attended the American Music Awards in this questionable getup. She opted for a red one-shoulder top that appeared to be unraveling and a pair of taupe-colored low-rise capris. Of course, we can't forget to mention Xtina's chunky black highlights that were curled beneath her atrocious hat!
Katherine Heigl certainly stayed covered up in 2005! The star arrived at the American Music Awards in a bizarre baggy all-ivory look comprised of a tank top, drawstring pants and a massive jacket on top. Though she was probably very comfy (and warm!), this was definitely one of the worst looks of the night that year.
Shania Twain donned an impossibly '90s look at the 1996 AMAs — a two-piece black PVC ensemble with a shiny cropped teal jacket over top. That night, the pop country queen picked up a pretty cool accessory — her very own American Music Award.
Emmy Rossum served up some beautiful ballerina vibes at the 2005 American Music Awards. The star stunned in this darling spaghetti-strap white frock, which featured a full tulle skirt. She finished things off with equally pristine white heels and a half-up, half-down hairdo that we still love all these years later.
Tori Spelling seriously channeled the late '90s with this coordinating look. From the sheer periwinkle long-sleeved button-up shirt and pants to the exposed midriff and those tightly curled ringlets, the "Beverly Hills, 90210" actress looked like a pop star at the 1996 American Music Awards.
Adorable! At the 2001 American Music Awards, Mandy Moore served up major girl-next-door vibes in this purple floor-length gown with delicate floral details.
One of the hottest couples on the 2003 American Music Awards red carpet? Kid Rock and Pamela Anderson, who stayed true to their individual styles. The Detroit musician donned an all-black look with an open shirt and cowboy hat and clutched a red Solo cup and Pamela sported a slinky black number that was open all the way down the side.
When it comes to fashion, Pamela Anderson has certainly had her share of hits… and misses. This look she wore to the 1997 AMAs? A miss. The Canadian actress-model opted for a slinky sheer gown with intricate red detailing. What she finished the look with? An obnoxiously large black hat.
At least it was memorable! Doja Cat, who's developed a reputation for her eclectic sense of style, attended the 2020 American Music Awards in this… rather interesting frock by Vivienne Westwood featuring an oddly shaped bodice trimmed in purple piping and a skirt with an excess of fabric gathered up to show off her lace-up purple heels.
We had one question for Sarah McLachlan back in 2008: Why? The star ruined a perfectly fine little black dress at the AMAs that year with a pair of opaque black tights.