By Megan Riedlinger
8:14am PDT, Apr 25, 2019
The Billboard Music Awards are back! The annual show returns to Las Vegas on May 1, 2019, and in honor of the fun night, Wonderwall.com is rounding up the most memorable fashion moments from the event from the last three decades, starting with a young Britney Spears! Back in 2000, Britney wore one of her most over-the-top ensembles to the Billboard Music Awards — an orange crushed velvet coat and, well, not much else. There appears to be a bra and a pair of purple tights underneath, all culminating in some equally crazy two-toned boots resulting in one of Britney's most totally out-there outfits. Keep reading for even more fashion flashbacks from Billboard Music Awards past!
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There's no question where the 10th Billboard Music Awards were held — just look at Christina Aguilera's crop top! The pop star showed up at the 1999 ceremony in this belly-baring shirt emblazoned with the city's name, Las Vegas, and finished off her look with a shiny pink maxiskirt.
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Jennifer Love Hewitt arrived at the 1999 Billboard Music Awards in this skimpy getup — a black strapless bandeau top with a sparkly skirt complete with a thigh-high slit and tie detail. As for accessories, she opted for black strappy heels and a gray fuzzy stole.
During the era of low waistlines, Paris Hilton nearly had a wardrobe malfunction with her particularly low-slung skirt at the 2003 Billboard Awards! She paired the white lacy piece with a metallic silver top, white heels and another relic of the mid-'00s — those over-the-top feather earrings.
Another star rocking a very daring silhouette? Celine Dion, whose creamy halter-style frock featured some seriously low cut-outs with bedazzled embellishments along the bust and hips. It certainly made an impression on the 2003 Billboard Music Awards red carpet!
Well, Shania Twain certainly made a splash at the 2003 Billboard Music Awards! The country superstar showed up in this confounding getup, which included a shredded, color-blocked shirt with a graphic of an open mouth across the chest, parachute pants and sneakers.
Anne Hathaway at the 1999 Billboard Music Awards? Yep, that happened! The star arrived in this strange frock — a strapless dress with a black velvet short-sleeved top half and a floral skirt that ended in plenty of fringe.
In 2017, Halsey showed up in this puzzling getup — a white bra by Sergio Hudson paired with a floor-length khaki skirt by Juun J. She accessorized the unfortunate look with gold hoops and gold bangles resulting in the worst look we saw that year.
A young "Candy"-era Mandy Moore attended the Billboard Music Awards back in 1999 in a bubblegum-pink turtleneck tank top — yep, that's a turtleneck — paired with a… well, let's just say a memorable floor-length pastel plaid skirt!
Miley Cyrus certainly made a statement at the 2013 Billboard Music Awards in this unique Balmain jumpsuit, which featured a black-and-white harlequin pattern juxtaposed with white lace all paired with simple black heels and a bright red lip.
Oh, this is a good one! Long before she was just Beyonce, Bey was in Destiny's Child. The trio attended the 2001 Billboard Music Awards in these mismatched looks. While Bey and Michelle Williams seemed to be somewhat matching in denim with pastel accents (that hat, Michelle!), Kelly Rowland opted for a polka-dot off-the-shoulder dress with thigh-high leather boots.
Beyonce was a vision in gold back in 2003 at the Billboard Music Awards. The star stunned in this Roberto Cavalli minidress detailed with beads and fringe. She paired the look with equally standout shoes — just check out those strappy floral-embellished heels.
Recognize this guy? A very casual — and buttoned up! — Kanye West attended the 2005 Billboard Music Awards. The rapper wore a while collared shirt, a brown cardigan, baggy white pants and sneakers for his appearance at the award show. Oh, how far he's come!
This one was memorable for all the wrong reasons. Maybe things were more casual back in the early '00s? Alicia Keys arrived at the 2004 Billboard Music Awards in… jeans and a tank top. Not only that, but it was a spaghetti-strap tank and unhemmed, too-long jeans that she opted to just cuff.
For her first Billboard Music Awards appearance back in 2011, Selena Gomez truly made an entrance. The pop star and former Disney darling showed off a more grown-up side when she donned this sleek black Dolce & Gabbana gown, which featured cutouts before they were ubiquitous. Her bright-red bow-topped heel selection kept things youthful and fresh.
Way back before Solange Knowles was known for pushing fashion boundaries, she attended the 2001 Billboard Music Awards in this shockingly simple (and casual!) ensemble. Beyonce's little sis rocked a printed silk maxiskirt with a white tank top and denim jacket, something we doubt she'd show up to an award show wearing these days!
Decked out in Balmain for H&M, Kendall Jenner made a splash at the 2015 Billboard Music Awards. The supermodel sported a beaded blazer with thigh-high boots and slicked-back hair for the music industry's big night.
Way back at the 1999 Billboard Music Awards, the newest pop princess on the block Britney Spears sported this simple and sweet lavender spaghetti-strap dress. Our favorite accessory? That prom-approved white shawl. So '90s!
Mila Kunis made an appearance at the 2016 Billboard Music Awards in this gorgeous Zuhair Murad minidress, which gave us major "Black Swan" vibes. The star wore the strapless, sparkly little number with a glam, sleek bun that brought the ballerina look full circle.
Leave it to Cher to always rock an unforgettable outfit on the red carpet! At the 2002 Billboard Music Awards, the diva sported this odd fringed getup that somehow channeled both a cowboy and a flapper at the same time.
Kesha redefined the LBD at the 2013 Billboard Music Awards. The singer wore this daring Givenchy minidress — and we mean mini — featuring a dangerously high slit on the side, which bared plenty of her backside.
If you hadn't already noticed, the Billboard Music Awards are known as an event where it's fine to show some skin. Jennifer Lopez proved that in 2015 when she donned this barely there Charbel Zoe Couture gown. The dress was covered in strategically placed sparkling embellishments, giving a nearly nude illusion.
Yuck! While we wish we could forget Rita Ora's 2015 Billboard Music Awards appearance, that awful Fausto Puglisi gown is burned in our memory. At the time, plenty of jokes were made about the gown's potential for wardrobe malfunctions, and we hated the tacky draping and clunky embellishments that seemed to be holding the white dress in place.
Fausto Puglisi strikes again! After that unfortunate Rita Ora look in 2015, Halsey donned the same designer at the 2016 Billboard Music Awards. The singer's strange confection, which came straight from the runway, featured slits and cutouts and mismatched geometric designs.
We love when stars throw unexpected curve balls on the red carpet! Janet Jackson attended the 2006 show in this surprisingly preppy menswear-inspired dress, which featured pinstripes, tie detailing and sleeve cuffs (sans sleeves)!
Madonna went for edgy but it looked more like a Halloween costume at the 2013 Billboard Music Awards. The Givenchy look, which included a fishnet dress, garters and a feather-collared bomber jacket, is one we wish we could forget.
Back at the 2005 Billboard Music Awards, Gwen Stefani accessorized with a flower crown and a baby bump! While pregnant with first son Kingston Rossdale, Gwen wore a sweet long-sleeved white minidress with a plunging neckline and a bow detail around the waist.
Mandy Moore arrived at the 2001 Billboard Music Awards in style! Perhaps taking a cue from the award show's home base, Las Vegas, Mandy went with this wispy white frock — which could have doubled as the perfect Vegas wedding dress!
Dua Lipa rocked this fun frock at the 2018 Billboard Music Awards — a vibrant purple Alexandre Vauthier number that featured a plunging neckline, long sleeves and a giant bow detail at the waist for some extra feminine flair.
Rihanna was a vision in white at the 2006 Billboard Music Awards! The superstar arrived in this sweet white minidress with a pretty ruffled embellishment below its plunging neckline. Completing this fresh look? Gold heels and stick-straight hair.
Taylor Swift went with an electric blue Zuhair Murad ensemble at the 2013 Billboard Music Awards. We loved this long-sleeved minidress on the superstar, and the way she rocked bangs and a high ponytail to complement the sultry look.
Kesha's 2018 Billboard Music Awards look was a puzzling one. She topped this intricate dress with a floral fringed kimono, a wide-brimmed hat and cowboy boots, making for a very Western-inspired look that came across as pretty excessive.
Vintage Britney! At the 2016 Billboard Music Awards, Britney Spears served up an outfit that would make '00s Brit proud: this tiny black lace look. It reminded us of her infamous black lace Dolce & Gabbana getup from the 2001 MTV Video Music Awards, but with the addition of a fun train.
Whitney Houston was a vision in red at the 1993 Billboard Music Awards where she rocked this high-necked lace jumpsuit that actually looks a lot like some of the fashion we've seen on the red carpet in the late 2010s! She paired it with even more red — bright red pointed-toe boots, to be exact — for a vibrant and very memorable look.
Artist Z LaLa made an impression at the 2016 Billboard Music Awards in this… well… indescribable ensemble, which included a hoop skirt featuring geometric cutouts with a matching headpiece.
Zendaya looked phenomenal in a two-piece Calvin Klein ensemble at the 2016 Billboard Music Awards. She accessorized her bralette and full-length skirt combo with a delicate choker and stacks of rings and bracelets resulting in a chic and memorable look.
This trend never really caught on, which is probably a good thing! At the 2000 Billboard Music Awards, Jessica Simpson rocked an LBD featuring a unique element that set it apart — feathered sleeves. Yep, the star's pink-and-magenta sleeves were completely separate from her tiny, strapless black dress. She then finished off her look with tall black boots.
Shakira, Shakira! We don't even know where to start! The superstar attended the 2005 Billboard Music Awards in tight black capri pants, a beaded black tank top and a black leather jacket with a fur-trimmed collar over top. And on her feet? Tall heeled black boots that almost met the hem of her capris. Yikes!
Nick Cannon wore one of the most questionable outfits in Billboard Music Awards history back in 2005 — this bizarre look that somehow managed to include a tie, a sweater, a dress shirt, printed shorts, sneakers and a backward baseball cap. It's actually sort of impressive!
Zendaya nearly shut down the red carpet in this killer Fausto Puglisi number she wore to the Billboard Music Awards in 2015. The black-and-white animal-print pantsuit featured a matching crop top and coral embellishments along the top and legs of the skinny pants. Finishing off this look? Another splash of color in the form of bright aqua pointed-toe heels that somehow made this ensemble even cooler (and matched her earrings!).
Iggy Azalea enjoyed one of her prettiest red carpet moments at the 2014 Billboard Music Awards when she wore burgundy Zuhair Murad. We loved the classy, sophisticated look on the rapper, as well as the gown's long sleeves and lace detailing.
At the 2016 Billboard Music Awards, Kesha used her magenta carpet look to pay homage to a legend — Prince! The star's purple velvet matador-inspired suit, which she wore with a white blouse and black ribbon tie, was her way of paying her respects to the recently departed icon.
Fifty shades of yellow! Way back before that reference made any sense, Usher stepped on the 1999 Billboard Music Awards red carpet in this all-yellow ensemble complete with a fur coat over top that was — you guessed it! — yellow too. The golden-hued look must have been a good luck charm: He went home with trophies that night!
"Call Me Maybe" cutie Carly Rae Jepsen showed up to the 2013 Billboard Music Awards in this disaster of a look — which included sheer netting that showed off her navel and weird embellishments that almost looked like wings.
Katy Perry looked like an iridescent dream at the 2012 Billboard Music Awards. The star wore this sparkly sleeveless number by Blumarine that dazzled with sequins and studs before giving way to a delicate tulle skirt.
Jessica Alba joined the music world for the 2016 Billboard Music Awards in this cute all-black, high-necked Zuhair Murad minidress. The Honest Company mogul added thigh-high boots to the long-sleeved dress to keep the look young and fresh, perfect for the Billboards.
Yikes! Faith Hill attended the 1995 Billboard Music Awards in this ensemble that was memorable for all the wrong reasons! The country crooner sported red evening gloves with a matching sleeveless satin minidress and black T-strap heels.
It's a safe bet that Kanye West wouldn't be caught dead in this look now, but back in 2004, he rocked a very colorful outfit to the Billboard Music Awards. He paired a bright argyle sweater with a white T-shirt, baggy jeans and a red jacket. Completing the look? Stark white sneakers.
Mary J. Blige really served up some interesting style at the 1995 Billboard Music Awards in New York City! The star went for an all-leather look — literally from the high neck of her long-sleeved jumpsuit down to her leather shoes. She added some funky shades and a big Fendi bag for some extra sass, making it all the more memorable!
Back at the 2014 Billboard Music Awards, Natasha Bedingfield arrived in baggy white pants, a black bralette and a sheer shirt with floral embroidery over top. Unfortunately, it turned out to be a disjointed mess of a look.
Pretty in purple! Carrie Underwood's 2006 Billboard Music Awards frock was fabulous. The rich purple minidress paired well with those metallic sandals.
A plaid sweater vest? Perhaps only Lil Jon could pull that off on a red carpet. The rapper rocked the questionable wardrobe element over a pale blue dress shirt and finished off his look with baggy jeans, blindingly white shoes and a pair of white sunglasses at the 2005 Billboard Music Awards.
We don't know any songs by Dencia, but we'll always remember this bizarre red carpet look she served up at the 2015 Billboard Music Awards. The artist arrived in this multicolored jumpsuit, complete with embellished 3D-detailing and futuristic shades.
Mariah Carey stunned in a hot pink minidress at the Second Annual Billboard Music Awards back in 1991. She paired her pretty spaghetti-strap ruched frock with metallic pink slingback heels for a memorably pink ensemble.
