45 Wildest Outfits Celebs Have Worn to Music Award Shows Over the Years

This article appeared in Thefashionball and has been published here with permission.

Wildest Award Show Looks

When you’re dressing for a very public event, you want to make sure you look eye-catching. For celebrities, drawing attention is a part of the gig. These stars definitely knew how to draw the camera’s attention. As awards season rolled around, these stars wore their weirdest and wildest outfits to different music award shows.

Grace Jones — 1983 VMAs

If there’s one thing that model, singer, and actress Grace Jones knows how to do, it’s to draw attention when she walks into a room.

Grace Jones — 1983 VMAs

At the 1983 VMAs, she brought her signature Avant-garde approach to fashion with this look. The most eye-catching thing about this look — aside from the space-age outline of the outfit — is the ultra-wide hat brim. Rick James even stopped to pose under it at one point!

Madonna — 1990 VMAs

In 1990, when Madonna attended the VMAs, she rocked a look that no one really saw coming from the pop queen at the time. It’s one few could forget.

Madonna — 1990 VMAs

When Madonna came on stage to perform “Vogue”, the singer had chosen one of the wildest ensembles of the night that better resembled the French Revolution than the ’90s pop scene. Like many performances, Madonna and her coordinated dancers somehow pulled the look off.

Pamela Anderson — 1999 VMAs

Pamela Anderson is well-versed in catching the camera’s eye when she hits the red carpet. The 1999 VMAs were no different.

Pamela Anderson — 1999 VMAs

One of her wildest looks from the awards show season relied on a variety of textures and patterns that definitely falls under the “maximalist” approach to fashion. The star wore sequined, patterned pants paired with a white corset and — perhaps the real focal point — an oversized, pink, fluffy hat.

Jennifer Lopez — 2000 Grammys

Awards shows are a great chance to show off the best designer looks on the red carpet. Jennifer Lopez really changed things with this green dress. The star wore the plunging green dress to the 200 Grammys.

Jennifer Lopez — 2000 Grammys

If the executive chairman of Google Eric Schmidt is to be believed, we can even thank this dress in part for the existence of Google Images. As for J.Lo herself, she said, “It was a nice dress. I had no idea it was going to become such a big deal.”

Pink — 2000 VMAs

Pink has long been noted for her distinct style. Back in 2000, at the VMAs, she went for a colorful look that we’re still talking about more than 20 years later.

Pink — 2000 VMAs

The star went for an eye-catching hairstyle that lived up to their name and from there, it was all gold and denim. In real early 2000s fashion, she opted for a crop top and a pair of jeans — with the waistband cut off, of course.

Toni Braxton — 2001 Grammys

There are some dresses that are ultimately rather simple but they still stand out for years to follow their appearance. That’s what happened with this 2001 Toni Braxton dress.

Toni Braxton — 2001 Grammys

Attending the Grammys, the singer wore a long white gown designed by Richard Tyler that left little to the imagination. When asked about the iconic dress, Braxton told US Magazine, “I’ve always gone a little risque with all my other awards [show outfits]. I decided that before I got married and had babies, I’d wear this.”

Macy Gray — 2001 VMAs

Musicians release new albums much to their fan’s delight all the time. However, the ways they might announce them might be different.

Macy Gray — 2001 VMAs

Macy Gray fans following the 2001 VMAs had the chance to see the release date of her then-new album — and all thanks to the dress she wore! The front read “My new album drops Sept. 18th, 2001” while the back demanded fans to “Buy it!” Who could say no to that order?

Britney Spears and Justin Timberlake — 2001 AMAs

Sometimes, our favorite celebrities can take current trends and really make them larger than life. Everyone loved denim in the early 2000s, right?

Britney Spears and Justin Timberlake — 2001 AMAs

Still, one of the wildest and most unforgettable outfits is hands-down Justin Timberlake and Britney Spears’ matching ensemble — which they wore to the 2001 AMAs. A full-length denim gown alongside a denim suit with a matching Stetson is a look that no one forgot.

Britney Spears — 2001 VMAs

Of course, you don’t become an icon like Britney Spears on one outfit alone. She’d attend the VMAs that same year with an iconic accessory.

Britney Spears — 2001 VMAs

Stepping on stage to perform her song “Slave 4 U”. The outfit was already a great look for Spears but what really made it memorable was the giant snake draped across her shoulders for the duration of the performance! It seems like this is an accessory that would take a lot of upper body strength.

Jonathan Arndt — 2004 CMAs

This snapshot of Martina McBride and Jonathan Arndt really shows how he went with the wildest options in his wardrobe to attend the 2004 CMAs.

Jonathan Arndt — 2004 CMAs

The outfit here is made up of pastels but the colors are only part of what makes it so shocking. The brocade jacket and fur collar really tie it all together to shock everyone seeing it. Plus, with all the jewelry and props, who could forget this look?

Eddie Montgomery — 2005 CMAs

Still, we’re not so sure that Big Kenny had the wildest outfit at the 2005 CMAs. It seems like Eddie Montgomery was ready to give him a run for his money. At an awards show where we’ve seen a lot of jeans and suits, this outfit definitely takes the cake.

Eddie Montgomery — 2005 CMAs

The long, embroidered coat already stands out for its silhouette but the musical notes, roses, and especially the bold letters reading “Broadway” across the front of the jacket undeniably make a statement.

OK Go — 2007 Grammys

The band OK Go definitely made a visual splash at the 2007 Grammys with some of the wildest outfits of the night. The band kept their faces covered with red fabric and donned matching body suits of red and gold brocade.

OK Go — 2007 Grammys

They were detailed, just like a regular suit, but also included a hood and matching accessories. One band member later said, “We’re dressed in the future — the future dressed us. This is actually us in an hour.”

Lady Gaga — 2009 VMAs

If there’s one musician that’s known for rocking some of the wildest outfits that Hollywood has seen, it’s Lady Gaga. She didn’t disappoint at the 2009 VMAs. The star started out in what seemed like a rather tame white outfit.

Lady Gaga — 2009 VMAs

That was until she took to the stage to perform her song “Paparazzi”. In a real moment of music meets performance art, Gaga committed to an intense number that left her stumbling on stage soaked in fake blood to finish the song off.

Nicki Minaj — 2010 AMAs

Nicki Minaj has sported some wild looks over the years. However, the outfit she wore to the 2010 VMAs might just be one of the wildest to date.

Nicki Minaj — 2010 AMAs

The coral-colored dress wouldn’t stand out too much on its own but Minaj knew exactly what details it needed. Who could look away from a dress with a golden exoskeleton like this? It definitely made for an unforgettable outfit.

Lady Gaga — 2010 Grammys

One of the outfits that Gaga debuted on her 2010 trip to the Grammys was this purple number that looks like it came straight from the future.

Lady Gaga — 2010 Grammys

The dress was made by designer Armani Privé and it even came with a sharp accessory. Lady Gaga actually wore this dress before she performed at the show for the very first time. It’s not a bad look for a debut at such a massive awards show!

Lady Gaga — 2011 Grammys

If you really want an outfit to stand out, you might want something really wild about it to draw people’s attention. Alone, the neutral outfit that Gaga wore isn’t too shocking.

Lady Gaga — 2011 Grammys

The shocking part was how she entered the event. Photographers waiting on the red carpet were greeted with a giant egg carried by a group of people, not the singer. Well, actually, she was just inside the egg, waiting for her chance to emerge. Did you know that she was actually in the egg for about 72 hours?!

Nicki Minaj — 2011 VMAs

To make an outfit the wildest one at an awards show, you really have to think outside of the box. What can you do that hasn’t been done before? Nicki Minaj definitely got wild with this silhouette and these fabric choices.

Nicki Minaj — 2011 VMAs

Her upper half is decked out in geometric patterns while the bottom half seems to take inspiration from some more comfortable clothes. Of course, you can’t leave home without your stuffed accessories either.

Katy Perry – 2011 VMAs

For the 2011 VMAs, Katy Perry went for a very geometric look. While Katy’s no stranger to eccentric outfits, this one was definitely surprising. The dress and top are fun but aren’t too shocking on their own.

Katy Perry – 2011 VMAs

What really made this look stand out was the choice of headwear for the look. We all know the right hat can bring a look together but we probably wouldn’t have thought of this accessory.

Miley Cyrus — 2013 VMAs

After her years at Disney ended, Miley Cyrus really started to take her looks up a notch at awards shows. Some of them have been really shocking!

Miley Cyrus — 2013 VMAs

The bejeweled outfit that she wore at the start of the show was great but didn’t necessarily stand out as weird or wild. That came later when she took to the stage in a bear leotard to perform “We Can’t Stop”. Of course, the giant dancing bears helped with the overall weirdness factor.

Frankie Grande — 2014 AMAs

Ariana Grande has stolen the show at many musical events. At the 2014 AMAs, though, it was brother Frankie Grande that stood out.

Frankie Grande — 2014 AMAs

This is one outfit that really highlights that sometimes it’s what you don’t wear that will make you stand out. It doesn’t take an eagle eye to see that Grande opted for a painted-on shirt. Like many others on YouTube at the time, Grande didn’t skip out on the neon hair either.

Katy Perry and Riff Raff — 2014 VMAs

Earlier, we took a look at Justin Timberlake and Britney Spears’ iconic matching denim outfits in the early 2000s. It seems like they weren’t the only ones who wanted to rock it either.

Katy Perry and Riff Raff – 2014 VMAs

For the 2014 VMAs, Katy Perry and Riff Raff decided to pay homage to the famous red carpet look. All in all, they recreated it rather well. It’s definitely reworked for their particular styles, though.

Miley Cyrus — 2015 VMAs

Of course, Miley Cyrus wasn’t going to get on this list for only one of her VMA looks. She pulled out another creative option for the 2015 VMAs.

Miley Cyrus — 2015 VMAs

She showed up decked out in a pink latex dress complete with balloon accessories reading “Do It” across the front — a nod to one of Cyrus’ own songs. Of course, she needed the perfect hair accessories and with so much pink, it seemed a pig bow was appropriate.

Baddie Winkle — 2016 VMAs

Who says that you have to stop donning your wildest looks as you age? That’s one myth that it seems that Baddie Winkle has been determined to make.

Baddie Winkle — 2016 VMAs

At the 2016 VMAs, she showed up in a body suit reminiscent of the look Britney Spears wore for part of her music video for “Toxic”. Naturally, Baddie Winkle wasn’t about to skip out on her accessories either. Even her cane is bedazzled to match the look!

CeeLo Green — 2017 Grammys

CeeLo Green is no stranger to attending awards shows. So, it makes sense that he knew just how to stand out when he donned this look.

CeeLo Green — 2017 Grammys

The star showed up to the 2017 Grammys in an outfit that was impossible to miss. He wore gold from head to toe, complete with gold gloves and a gold helmet, so nothing but gold was showing. The memorable look definitely got fans talking.

Cardi B — 2019 Grammys

Cardi B looked her best in this dress that really brings to mind Botecelli’s Venus emerging from the sea. There’s more than just a silhouette here, though.

Cardi B — 2019 Grammys

The dress was made by Mugler and it has no shortage of pearls and silk to pull the look together. She even has a tower of pearls in her hair! She was dressed to impress — and that she did. In fact, later that night, she became the first woman to win the Grammy for Best Rap Album.

Sophie Turner — 2019 Billboard Music Awards

Sophie Turner skipped the usual gown for a bodysuit at the 2019 Billboard Music Awards. The look was bold and it definitely caught people’s eyes.

Sophie Turner — 2019 Billboard Music Awards

The getup brought a variety of opinions from critics but a few things made the outfit stand out. For one, the pattern of the silver bodysuit stood out. The silhouette also stood out, thanks to the sharp shoulders hanging a little lower than shoulder pads would.

Billy Porter — 2020 Grammys

Billy Porter knows exactly how to stop the paparazzi with his red carpet looks. The American Horror Story alum had one of his wildest looks for the 2020 Grammys.

Billy Porter — 2020 Grammys

For this look, Porter was head to toe in sequins, adding silver tassels on his hat and pants legs. The fringe on the hat was more than just decorative, though. At Porter’s command — or his stylist’s — the fringe opened to reveal the actor’s face.

The Weeknd — 2020 VMAs

There are some looks at the VMAs that really stand out for the effects that go with them. The suit The Weeknd wore to the 2020 VMAs wasn’t too shocking.

The Weeknd — 2020 VMAs

His makeup, on the other hand, caught people’s eyes. After all, it was a pretty realistic rendering of what he might look like after a fight. The look ended up being promotional for his new video and he’d don it again a few more times the next year.

Doja Cat — 2021 VMAs

Doja Cat has often challenged expectations when it comes to fashion. This look really is no different but it surprised many viewers. In 2021, the singer attended the VMAs in this number.

Doja Cat — 2021 VMAs

Well, she wore a few different outfits throughout the night but this one was by far the most memorable. She donned this getup onstage while accepting a VMA award, admitting that “I look like a worm. That’s done. I never thought I’d be dressed as a worm while accepting an award.”

Machine Gun Kelly — 2022 AMAs

More than once, Machine Gun Kelly has made headlines for some outrageous outfits at various events. This one really turned some heads, though.

Machine Gun Kelly — 2022 AMAs

A purple suit really isn’t that shocking at the AMAs. In 2022, Machine Gun Kelly wore this purple suit to the AMAs and it’s easy to see why it stood out. If nothing else, it would definitely keep people from getting into your personal space.

Lizzo – 2023 Grammys

Lizzo has skyrocketed to fame and it’s easy to see why! The star makes great music and has a charming personality that draws fans in. She made an impression in florals at the 2023 Grammys.

Lizzo – 2023 Grammys

The singer had a two-layered look. The base of the look is an orange gown that’s gorgeous in its own right. However, it was the cloak of roses that really made this outfit as memorable as possible.

Harry Styles — 2023 Grammys

There are some stars that need no introduction. At this point, it seems like Harry Styles definitely qualifies as one of these superstars.

Harry Styles — 2023 Grammys

The star opted for a multi-colored jumpsuit. It could almost look like a patchwork pattern if all the pieces weren’t given a sequined effect to make sure this wild look still catches the light.

Alisha Gaddis — 2023 Grammys

Lizzo wasn’t the only one to bring florals to the red carpet at the 2023 Grammys. It was a trend Alisha Gaddis decided to play into as well. Still, the two gowns have a lot of differences.

Alisha Gaddis — 2023 Grammys

Compared to Lizzo’s more monochromatic look, this colorful piece gives us a variety of flowers. It’s a gown that almost brings to mind Florence Pugh’s flower-covered look in Midsommar.

Sam Smith — 2023 Grammys

Sam Smith stood out on the red carpet at the 2023 Grammys but they were ready with an entire ensemble look with a few other stars.

Sam Smith — 2023 Grammys

In all, they showed up with Kim Petras, Violet Chacki, Gottmik, and more. They led the crew in a red cloak and gloves, complete with a cane and top hat. If that wasn’t interesting enough, the top hat featured a veil too.

Shania Twain — 2023 Grammys

There are some stars who just know how to get the camera’s attention. Shania Twain definitely did that for the 2023 Grammys.

Shania Twain — 2023 Grammys

The singer went for a head-to-toe cow print look. With a massive printed hat and bell-bottom pants, we literally mean from head to toe. Now, would it really be a glam red carpet look if those cow spots weren’t sequined?

Blac Chyna — 2023 Grammys

Blac Chyna knows how to work the spotlight but even this look was surprising to many fans. Who could have expected it? The short dress brings to mind images of the Black Swan.

Blac Chyna — 2023 Grammys

Of course, it seems like Blac Chyna took things to the extreme. Wouldn’t it be pretty hard to do ballet in an outfit like this? One thing is for certain — this dress had no shortage of different textures to experiment with.

Dencia — 2023 Grammys

Dencia had another iconic look to bring to the 2023 Grammys. It seems like everyone really brought out their best at this event! Dencia’s look was almost the classic black gown.

Dencia — 2023 Grammys

Instead of a plunging neckline like J.Lo, though, she opted for a high collar encrusted with blue and green jewels. If you look closely, her dress also has black jewels nestled into the fabric as well. The cobra-like dress really captured everyone’s attention as she made her way across the red carpet.

Lucky Daye — 2023 Grammys

If you want to wear a black suit to the Grammys, you have to think a bit outside of the box if you want to stand out. Lucky Daye accomplished that. To start, it’s not just a black suit.

Lucky Daye — 2023 Grammys

To catch the lights, there are sequins all over the outfit to make it shine. What really sets it apart, though, is the melting metallic piece to the puzzle that honestly looks a little hard to move around in.

Billy Dean — 2003 CMAs

The CMAs aren’t often known for having some of the wildest outfits of the awards season as you might expect at the Grammys or VMAs. Still, that doesn’t mean that there aren’t any outfits to write home about.

Billy Dean — 2003 CMAs

In 2003, Billy Dean took to the carpet in an embroidered suit that no one was going to forget anytime soon. The back featured an embroidered American flag and the rest was decorated with stars and eagles. Very patriotic!

Jeff Bates — 2003 CMAs

It seems like Billy Dean wasn’t the only one interested in embroidered jackets when the CMAs rolled around in 2003. Jeff Bates jumped on the bandwagon too, although the design he opted for wasn’t quite as patriotic.

Jeff Bates — 2003 CMAs

Instead, it was an eclectic mix of skulls, vines, roses, dice, cards, and more. From the looks of it, this jacket was definitely an eye-catcher. This is one trend that it seems like everyone loved at the 2003 CMAs.

Big Kenny — 2005 CMAs

In 2005, the CMAs hosted some eccentric looks and outfits. Take a look at this photo, for instance, which features Big Kenny and John Rich.

Big Kenny — 2005 CMAs

We could spend some time on John Rich’s two-toned denim but it’s Big Kenny’s outfit that sticks out to us more. It seems almost as likely that he’s going to step on stage to give us a production of Les Miserables as he is to accept an award.

Kenny and Christiev Alphin — 2009 CMAs

When you’re coming to an awards show as a couple, it opens up a lot of opportunities to come up with the wildest outfit you can think of together.

Kenny and Christiev Alphin — 2009 CMAs

Just the suit and dress that Kenny and Christiev Alphin chose for their red-carpet look wouldn’t have stood out too much. No, what really makes these 2009 CMAs look stand out so much is the matching top hats that really made this so memorable.

Dillon Francis — 2022 Grammys

Usually, when you hit the red carpet, you want to look your best. For most stars, this means breaking out the mind-bogglingly expensive suits and gowns.

Dillon Francis — 2022 Grammys

Dillon Francis thought well outside of the box and showed up in something no one was expecting when the 2022 Grammys rolled around. After all, not many people walk the red carpet in jeans and a t-shirt, carrying the snacks they bought from Walgreens on the way.