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34 Daring Looks Celebrities Have Unveiled In 2021

Lockdowns the world over have seen many of us glued to the sofa in our old and scruffy sweatpants. But celebrities? They’ve still pulled out all the stops to dazzle us with their daring style. From awards to premieres, to — of course — the Met Gala, let’s take a peek at 34 of the boldest and bravest looks from showbiz this year.

34. Serena Williams, Met Gala

Tennis legend Serena Williams swept into the Met Gala in a mesmerising cape of pink feathers. The ombré shawl travelled right down to the ground, enveloping Williams in a flow of pink shade. And underneath? A silver-laced bodysuit designed by Gucci and decorated with pink glittery stars, of course! “[Williams] served a royal look tonight,” her husband, and Reddit co-founder, Alexis Ohanian posted proudly on Instagram. Certainly it was an outfit befitting the 23-times-Grand-Slam-winning “Queen of Tennis”! 

33. Kate Middleton, No Time to Die premiere

Wow! In an outfit fit for a duchess, Kate Middleton quite literally dazzled crowds at the London premiere of No Time to Die. For the glamorous event, the royal slipped into a golden gown dreamed up by one of her favourite designers — Jenny Packham — complete with a floor-length cape. The ensemble was completed by sequins and beads, and golden O’nitaa earrings just made the overall look even more shimmery. People magazine reported that Daniel Craig told Kate, “You look jolly lovely.” She’s a real-life golden Bond girl! 

32. Kim Kardashian, Met Gala

Kim Kardashian arrived at the Met Gala in a look that immediately became a meme and we can see why! Head-to-toe in black, Kim’s floor-length ponytail was the only part of her that was exposed. The black-out look, designed by Balenciaga, was made up of a bodysuit underneath a T-shirt dress, matched with a balaclava and gloves. But in true Kim K style, the star was complete with a face full of makeup hidden beneath, as revealed on Instagram by her makeup artist Mario Dedivanovic. Confused? Well, “American Independence” was the theme of the event, and, as Kim herself remarked, “What’s more American than a T-shirt head to toe?”

31. Lil Nas X, Met Gala

Three bold looks over the course of the year is pretty impressive. But three in one night? Lil Nas X is certainly dedicated to the cause! For his first Met Gala, the Old Town Road singer arrived at the Metropolitan Museum of Art in a golden cape – and flowing train – fit for new music royalty. Next, he revealed a golden suit of armour that was shiny enough to see your reflection in. Nas finished the look in a sparkling – you’ve guessed it – golden Versace bodysuit! 

30. Harry Styles, GRAMMY Awards

Harry Styles had a duty to impress on the red carpet of the Grammy Awards. He started the event with a performance of his cheeky hit single, Watermelon Sugar, after all. He was also up for a few awards, and in true superstar fashion he wore three different outfits, all featuring feather boas! He kicked off proceedings in a look we like to call ‘Granddad-chic’: a clashing plaid blazer and sweater, brown bell-bottoms and a purple boa. How does he pull it off?

29. Billie Eilish, Met Gala

As co-chair of the event, Billie Eilish mesmerised fans at the Met Gala in a pale-pink Ocar de la Renta ball gown. Wanna know what made this look even more bold? It’s totally different to the singer’s usual baggy clothes and dark hair. The creative director of Oscar de la Renta, Fernando Garcia, revealed to The New York Times that Eilish wanted to surprise everybody with “a look she hasn’t done before.” With a massive 15-foot train and glittering Cartier jewellery, she looked every inch the girly-girl. In fact, Vogue magazine claimed that the gown was influenced by Marilyn Monroe’s 1951 Oscars outfit. 

28. Dan Levy, Met Gala

Dan Levy, star of Schitts Creek, wore an intricate look of which his on-screen persona, David Rose, would be proud. For his first Met Gala, the actor wore a Jonathon Anderson creation with statement puffy sleeves and a map design. If that wasn’t interesting enough, the design is actually an adaptation of artist and LGBTQIA+ activist David Wojnarowicz’s work. Levy told Vanity Fair magazine he wanted to reflect Wojnarowicz’s celebration of “queer love and queer visibility,” while also sending a reminder that “there’s a lot more that needs to be done.” He continued, “I think that has always kind of been what the Met has embodied... It’s not just clothes, you’re celebrating the impact that fashion can have.”

27. Halle Berry, Oscars

Movie legend Halle Berry was called into action as an award-presenter at this year’s Oscars. For the occasion, the “Best Actress” winner wore a strapless mauve dress designed by Dolce & Gabbana, with flowing fabric and a bow at her midsection. But what really caught the attention was her bold new hairstyle. Moments before appearing on the red carpet, Berry teased the chop on her Instagram account, showing a pile of hair on the floor. She didn’t disappoint, later revealing an angled bob with short bangs. Berry told online paper Huffington Post, "I am my best self when I have super-short hair.” Well, short hair certainly brought the actress luck for her 2002 Oscar win!

26. Timothée Chalamet, Met Gala

For what has been referred to as “fashion’s biggest night out,” Timothée Chalamet broke all the rules. As co-chair of this year’s event, we guess he’s kind of allowed. The actor wore white sweatpants tucked into socks, and white classic Chuck Taylor Converses. Well, the actor actually walked a whole ten blocks to the event, which he recorded on an Instagram livestream for his millions of followers, so we suppose he had to keep comfy! Attendees of the event usually choose one designer to wear, but Chalamet continued to break the rules. He told Keke Palmer, host of the event, that his look included a “mix of everything!”

25. Jake Gyllenhaal, Tony Awards

Jake Gyllenhaal was tickled pink on the red carpet for the Tony Awards. The actor cut a bold figure in all rose, including a — you’ve guessed it — pink satin cummerbund. He might have missed out on the award for which he was nominated, but he’s a fashion winner in our eyes!

24. Billie Eilish, No Time To Die premiere

Eilish looked every inch the chic Bond villain in this rather adrongynous ensemble. The singer-songwriter wore a black sparkly jacket over a shirt of the same print, paired with baggy trousers and chunky Gucci heels. Eilish was sort of a guest of honor at the event, as she wrote and sang “No Time to Die”, the title track of the most recent Bond release.

23. Jennifer Lopez, Joe Biden’s inauguration

Jennifer Lopez looked a vision earlier this year at Joe Biden’s inauguration. True, Kamala Harris and Jill Boden both donned bright colours, but J-Lo still stood out in her dazzling white outfit. Well, her choice was no accident. The pure tone paid homage to the suffragettes, as it was one of three significant colors they used to signify their battle to win the right to vote for women. The matching tweed jacket, blouse and trousers complete with sequins were all designed by Chanel and only added to the spectacle of her performance of “America the Beautiful”.

22. Kaley Cuoco, Emmy Awards

Kaley Cuoco dazzled fans in her neon-yellow dress at the Emmy Awards. The gown, custom made by Vera Wang, included a daring split up her thigh and was paired with matching strappy heels. The outfit also had flowers adorned onto the straps, which only served to make the look even more bold. We think this was a great choice of outfit for the actress’s first red-carpet appearance since her split from husband Karl Cook. 

21. Nick Jonas, Billboard Music Awards

We’re green with envy at Nick Jonas’s bravery in wearing such a cool outfit! The singer wore a baggy green jacket, trousers, and silk blouse to host the awards. His appearance was even more special bearing in mind he’d suffered a bike injury just a few days before. The singer tweeted: “I started this last week by taking a brutal tumble on a bike fracturing my rib and ended it hosting the @bbmas with my incredible wife by my side who helped me every step of the way to recover and feel my best”.

20. Meghan Markle, school visit

Red alert! In a far cry from the muted colours and demure outfits she wore as a royal, Meghan Markle wore this ensemble to read her book, The Bench, to a group of second-grade pupils at an elementary school in New York. From the heels to the jacket, she looks very chic in this raspberry outfit, which is perfect for fall.

19. Maisie Williams, Met Gala

Is that really you, Maisie Williams? The actress totally transformed her appearance for the Met Gala this year. We’re getting serious goth vibes from the leotard dress, mesh sleeves and tights, and black crystals. For this look, Williams transformed her blonde locks to match the all-black outfit. The Game of Thrones actress told TV’s E! News that the outfit was designed by her beau, Reuben Selby, and inspired by The Matrix.

18. Haim, Grammy Awards

Seeing triple! Sister power trio Haim looked quite the girl group in their matching blue outfits. Este, Danielle and Alana Haim all wore custom Prada ensembles, but each with their own individual twist — one with cut outs, one with pants and one with a turtleneck.

17. Anya Taylor-Joy, Emmy awards

As Coldplay would doubtless have observed, it was all yellow! Mirroring her entrance into the world of acting, Anya Taylor-Joy took the Emmys by storm. Her sunshine-toned dress, designed by Christina Dior, was a paler shade than the billowing bright-yellow shawl that trailed behind her in a dramatic train. The look is certainly fit for a darling of the screen!

16. Lady Gaga, Joe Biden’s inauguration

Wow! Lady Gaga is used to bold looks — remember that meat dress? But for Joe Biden’s inauguration, the singer remained true to her roots while retaining an element of class. To sing “The Star Spangled Banner”, Gaga wore a custom-made Schiaparelli design, featuring a navy-blue jacket with a golden bird, which then gave way to a bright-red billowing dress. Her hair was braided with a black ribbon and her lips were a dramatic red. And to make the look still more outré? The dress was actually bulletproof! The singer told Vogue, “That has to be one of the proudest days of my whole life”. Well, she has the outfit to match!

15. Dan Levy, Golden Globes

Dany Levy made fashion history at the virtual 2021 Golden Globes. According to GQ, his eye-catching, sequin-covered outfit marked the first time Valentino had ever created haute couture for men. The magazine declared at the time that Levy’s look “was a lesson in how to upstage even the coveted Golden Globe awards themselves.”

14. Taylor Swift, Grammy Awards

Taylor Swift looked a pretty petal at this year’s Grammy awards. To pick up her award for Album of the Year for Folklore, Swift wore a suitably dreamy ensemble. The nude mesh dress was adorned with a garden of flowers and actually featured 3D embroidery to make the blooms really stand out. The singer completed the ensemble with some delicate pink heels that ensured all eyes remained on the springtime look.

13. Phoebe Waller-Bridge, No Time To Die premiere

True to form, Phoebe Waller-Bridge startled with an androgynous look for the No Time to Die premiere. The actress wore an Azzaro Couture black sparkly jumpsuit which plunged down to her midriff. The eye-catching outfit certainly flattered the co-writer of the latest Bond installment. And an equally sparkly white jacket elegantly draped over the shoulders finished off the ensemble perfectly. 

12. Micaela Coel, Emmy Awards

Micaela Coel stunned onlookers at this year’s Emmy Awards. She donned a bright-yellow outfit designed by Christopher John Rogers, which contrasted beautifully against the red carpet. The two-piece included a strapless top, which had a train detail, and a floor-length skirt. Coel was up for nine nominations for the series she wrote and starred in, I May Destroy You. And she became the only black woman to date to win in the “Outstanding Writing for a Limited or Anthology Series or Movie” category.

11. Jackson Lee, Golden Globes

Jackson – Spike Lee’s son – joined his sister Satchel to serve as the Ambassadors for the 2021 Golden Globes. And he also dressed to impress, of course – wearing a bright and stylish ensemble quite unlike the standard for men on the red carpet. He had on an almost all-Gucci outfit, but the shoes were Jordans and the sunglasses were actually by Magic Johnson’s daughter Elisa.

10. Billie Eilish, Grammy Awards

As should be clear by now, Eilish is no stranger to bold outfits, and her choice for the Grammy Awards did not disappoint. Eilish wore a Jacquard shirt, trousers, bucket hat — and even a mask — which all had the same floral print. And to top it all off, the singer actually matched her manicured nails to the print on her outfit!

9. Sarah Jessica Parker, And Just Like That… set

Sarah Jessica Parker’s alter-ego, Carrie Bradshaw, is fashion royalty. And Parker did not disappoint fans on the set of the follow-up TV drama series, And Just Like That... Known for her clashing styles, the fictional character wore a striped jumper over the top of a billowing white tiered gown. We can’t wait to see what other fashion surprises the show has in store!

8. Catherine O’Hara, Emmy Awards

Catherine O’Hara cut a bold figure in the one-shouldered outfit she wore to the Emmy Awards. The Schitt's Creek actress turned up in all-red attire of which we think her on-screen alter ego, Moira, would have beed proud.

7. Kim Petras, Met Gala

Um? Kim Petras turned up in a bizarre outfit to this year’s Met Gala. Her outfit included a 3D horse head bustier and a voluminous skirt with roses and apples. And her mane? It was suitably tied into a long braided ponytail that was probably longer than what hangs from a real horse’s rear end. Designer Taymour told Vogue, “I just wanted to work with a chill, easy-going person, and that’s exactly who Kim is”. We’d never know from her outfit!

6. Cardi B, shopping

Where to begin? We’re not quite sure what’s going on with this look. This outfit is sheer, but also has a red-toned body painted on to the fabric. The overall effect is confusing, but certainly eye-catching!

5. Beanie Feldstein, Tony Awards

Beanie Feldstein turned heads in her lime-toned outfit at the Tony Awards. The actress wore a dress by Christian Siriano that had a billowing collar. She continued the bold look all over, matching the dress to her green skyscraper heels.

4. Noah Cyrus, Grammy Awards

Noah Cyrus wowed fans at the Grammy Awards in a massive white dress that seemed to swallow the singer whole. Cyrus was nominated for Best New Artist, and chose the dress, designed by Schiaparelli, for the occasion. InStyle magazine spoke to Cyrus’s stylist, Brett Nelson, before the event, and he said, “The Cyrus family is legendary in the music industry... so I wanted something that felt very original and iconic for her. I wanted to do something that felt a little bit more art-based. She’s a cool little art kid, so I want to show that.” Mission accomplished, we think!

3. Iman Khan, Met Gala

Iman Khan looked heavenly in her outfit for the Met Gala. The golden girl wowed in a one-of-a-kind Harris Reed design. The bustier and trousers were worn underneath a caged overskirt which had golden feathers and matched her massive headpiece. The effect looks positively otherworldly! The supermodel tweeted "@harris_reed If you ever wondered what a dream coming true looks like… this is it!”

2. Cynthia Erivo, Golden Globes

Cynthia Erivo wore a spectacular neon green number to the 2021 Globes. Her stylist Jason Bolden raved about it to E! News, saying, “[Erivo] knew nothing about this dress, but she trusts me and allows me to be creative. The shoes are like skyscrapers; the color and the shape is so bold – and why not?! – to add some much-needed fantasy. The neon green tea-length dress reminds me of scuba fabric.” It shouldn’t have worked, but it did.

1. Meghan Markle, Global Citizen Live Concert

Meghan debuted a whole new look at the Global Citizen Live concert in September 2021. She was back in a short white dress, similar to the ones she’d worn before becoming a duchess, but this one was perhaps a little more sophisticated. Meghan’s style has definitely become less formal now that she’s stepped down as a senior royal, and this look epitomizes this shift.

2021 certainly saw some bold fashions choices, but frankly, they’re tame in comparison to the eye-popping looks the MTV Video Music Awards has seen over the years. Since the event’s debut in 1984, the attendees have had just one rule to follow: there are no rules! We’re talking dangerously sheer dresses, cowboy costumes, a gown made of raw meat… you get the picture. So, keep scrolling for the most daring outfits to appear on the VMAs red carpet – so far, anyway.

Cher-ing a lot

Cher fans will know that when she and Bob Mackie get together, sparks fly. The designer has dressed the songstress for decades, draping her in sequins and sheers that stun every single time. And when she showed up at the 2010 VMAs in the Mackie-made getup she’d sported in the video for “If I Could Turn Back Time,” it was perfect – just like everything else Cher does.

The right fluff

Coco Chanel once famously gave the following advice to help women obtain her effortless, classy style. “Before you leave the house,” the legendary designer said, “look in the mirror and take one thing off.” We assume that Pamela Anderson didn’t know of that quote before attending the 1999 VMAs in sequined pants, a corset and a fluffy, oversized top hat.


Busta Rhymes is no stranger to colorful clothes, but the outfit he wore to the 1997 VMAs is in a league of its own. The hip-hop star made waves with his cherry-colored, intricately patterned kimono, paired with matching pants and shoes. And 20 years on, Cosmopolitan named the ensemble as one of the most outrageous outfits ever to be seen on the red carpet, although the magazine also felt that the “kimono… should have never seen the light of day.” We totally beg to differ.

Spaced-out silver

There’s an otherworldly vibe to Lenny Kravitz’s outfit from the 1993 VMAs. The jumpsuit-esque silhouette and shiny silver fabric make him look like an outer space explorer. And the fact that he’s holding the iconic MTV Moonman just adds to the extraterrestrial chic. Lenny, is there something you’re not telling us?

Masked and multicolored

Lady Gaga’s not really one to dress subtly at the VMAs – or anywhere else, for that matter. And this look from the 2020 ceremony is a case in point. After winning the award for Best Collaboration – an honor she shared with Ariana Grande for their tune “Rain on Me” – Gaga collected her statuette in a bright pink gas mask and psychedelic frock with spikes that resembled those on a lionfish. As you do.

Grilled cheese

Katy Perry in a leopard-print gown with a slicked-back high ponytail? There’s not much that’s ground-breaking about that. But the songstress makes our list because of what’s happening with her teeth. Yep, the “Firework” singer showed up to the 2013 VMAs with a full grill on her pearly whites. Talk about fierce!

In this skin

Jessica Simpson’s 2005 VMAs look combined everything that we loved to wear at the turn of the millennium. Over shorts, she wore a flouncy lace blouse, a waist-cinching belt, an exposed bra and, of course, dramatic smokey eye makeup. Personally, we’re okay with it taking a few more decades for this kind of fashion to come back into style.

Stuff of legends

Who says MTV doesn’t respect real music? At the 1991 VMAs, famed guitarist Steven Van Zandt and funk legend Bootsy Collins were both in attendance. And the icons dressed to impress – or at least stun – if their colorful, bright and bedazzled outfits are any indication.

Mixed messages

Some say Fergie wore this strange outfit to the 2006 VMAs as a reference to The Dutchess, the album she’d dropped that year. But that collection was inspired by London, and we’re seeing much more of an Irish vibe in her getup. Maybe it’s the tiny green tie or the cute hat? Neither would be out of place on a leprechaun.

Fringe fest

By now, you’re realizing that there’s no dress code on the VMAs red carpet. Fringe-covered, sunset-hued and turquoise-accented gowns? Perfect! And Destiny’s Child dared to go matchy-matchy in this very combination to the 2001 VMAs in New York City.

Making a point

See a cone-shaped bra, and you probably think of Madonna. And nearly 30 years after the singer dared to sport Jean-Paul Gaultier’s iconic creation on stage, the style is still inspiring others. Like Cardi B, for example! On the 2017 VMAs red carpet, she memorably appeared in a dress that seemed to pay tribute to the Queen of Pop with its bodice.

Nightie on the town

Sofia Coppola’s purple nightie was clearly too pretty to keep hidden in a bedroom. So, she slipped the sheer garment on top of some underwear and headed to the 1995 VMAs. Or maybe she just overslept for the ceremony? In any case, the director’s daring outfit made awards fashion history.

Bella Ha-did that

Talk about abs-olutely stealing the show! That’s what Bella Hadid did in the midriff-bearing dress she wore to the 2019 VMAs. Calling it a dress is a stretch, really, as it looks more like a form-fitting skirt and bandeau attached together with suspenders. But while we get to the bottom of this conundrum, one thing’s for sure: the model pulled her look off with ease.

Going for the gold

Cut-outs aren’t exactly a new thing on the VMAs red carpet. Back in 1990, MC Hammer turned heads with his shimmering gold blazer complete with strategically placed rips. If that wasn’t enough, the rapper wore glitzy, matching pants to bring the whole look together. And, yes, those pants were baggy...

Butterfly Beyoncé

Beyoncé had a good night at the 2016 VMAs, and we’re not just talking about the stunning outfit she wore. The electrifying singer brought home eight gongs from the ceremony, you see. And she raked in all of those awards in a seafoam-and-sheer gown with dramatic, butterfly-wing-esque shoulders.

Suspending our disbelief

Miley Cyrus isn’t known for her subtlety, and that applies both to her memorable performances and her fashion choices. So when she showed up at the 2015 VMAs in this daring, silver, space-y getup from Atelier Versace, we doubt anyone was really surprised.

Leather weather

The 2001 VMAs took place in New York City on September 6. The average temperature in the Big Apple at that time of year is about 75° F. But despite the heat, songstress Alicia Keys showed up in a head-to-toe leather outfit. And she probably didn’t care about the discomfort when she brought home a Moonman of her own.

If it ain’t broke…

It looks like Jessie J’s bedazzled crutches, gem-colored tights and boot were part of some avant-garde fashion statement. But they’re not just for show. Before the 2011 VMAs, the singer fractured her foot, meaning she had to update her red-carpet look. And prior to the ceremony, she told MTV that she was going to “pimp out [her] crutches” – a promise she seems to have kept.

Rita in red

Rita Ora turned up the heat at the 2014 VMA awards when she arrived in this head-turning red gown. It made such an impression that we remember it like it was yesterday. In a post-event interview with British radio station Capital FM, Ora revealed that red is, in fact, her favorite color. And of that infamously high slit, she said, “It just kept getting shorter and shorter, and the thigh just kept getting higher and higher! Until I thought ‘OK, we have to stop now!’”

Cowboy classic

Lil Nas X’s song “Old Town Road” topped the Billboard charts for a record-breaking 19 straight weeks. It also made country-rap an actual thing. So someone had to give the guy a Moonman. And the up-and-coming star showed up to accept his award in an outfit worthy of all his accomplishments: a bright red cowboy getup. Well, obviously...

Getting it white

Remember when Jennifer Lopez and Diddy dated at the tail-end of the ’90s? If you don’t, then you surely recall the famous V-neck Versace gown J.Lo wore to the 2001 Grammys – the green, jungle-print one that seemed to be holding on with a little bit of tape and a lot of hope. And this all-white ensemble for the 2000 VMAs is a close second in the ostentatious stakes.

Belting it out

Leave it to a supermodel to make an impression on the red carpet. Cindy Crawford turned heads – and probably dropped some jaws – when she showed up at the 1992 VMAs in a rough-edged Versace look. And if the multiple buckles and straps weren’t risqué enough, the sheer panels definitely got the message across.

Light bright

Taylor Swift tends to change her style with every new album she releases. So, when Lover came out in 2019, she ditched her Reputation-era serpents and dark hues for a lighter, softer style. Brighter, too, if the sequin-covered Versace look she sported at the 2019 VMAs is anything to go by.

Blue it

Only at the MTV VMAs would an attendee think, “I should pair my bralette top with my hair.” But that’s precisely what appears to have crossed Gwen Stefani’s mind before attending the 1998 ceremony. And if that wasn’t outlandish enough, the singer chose to wear a skirt over her jeans and plaster her body in henna tattoos, too.

Tiny Leather Clothes

Can you guess the inspiration behind TLC’s outfits from the 1999 VMAs? Well, as you can see, the group’s members – Rozonda “Chilli” Thomas, Tionne “T-Boz” Watkins and Lisa “Left Eye” Lopes – wore head-to-toe leather. Billboard claims, though, that the trio got the idea for their look from mermaids, of all things. How did we not think of it?!

A truly cropped top

Crop tops today generally tend to skim the navel and show off just a bit of belly. But the 2000s were a different beast, and wearing a midriff-baring top meant flashing, well, your entire stomach. Christina Aguilera embodied that trend at the 2002 VMAs in her barely-there halterneck and very low-rise skirt.


Jared Leto attended the 2017 VMAs with his 30 Seconds to Mars bandmates. But the musician and actor made sure he stood out from the pack – and could be seen from space – in his completely sequined, knee-length cape in shades of blue, green and red.

Harajuku nightmare

Rolling Stone deemed Nicki Minaj’s outfit the “most confusing” getup seen at the 2011 VMAs. The rapper seemed to have been influenced by Japan, but beyond that? The magazine pondered, “Is her get-up a tribute to Metropolis, the stuffed animal aisle at Toys ‘R’ Us or something else entirely? She even taped her mouth shut – rendering her literally speechless. Well, so were we.” Us, too.

Tanked it

On the 1995 VMAs red carpet, Dennis Rodman slipped into a shimmering camisole and juxtaposed the delicate top with bulky, baggy jeans. Yes, really! And while some naturally hated the look, V magazine named the outfit one of its favorites in VMAs history and lauded Rodman for his “coolness off the court.” Which side of the divide do you fall on?

My only anemone is myself

We have to be blunt: Pink’s fluorescent locks at the 2000 VMAs really made her head look like a sea anemone. And things didn’t get much better from the neck down, as the singer paired her rose-colored strands with a floor-length fur coat, gold halter and shockingly low-rise jeans. We’d rather watch from the couch in our sweatpants.

Not feeling blue at all

Shiny, skin-tight blue fabric from head to toe? Matching hair ties? A thick layer of eyeshadow and a huge hoop earring? There’s only one person who could put all of this together and look amazing: Prince. He blue it out of the water at the VMAs in 1999.

Know what I jean?

Once upon a time, boy-bander Justin Timberlake dated the princess of pop, Britney Spears. And, without doubt, the duo’s greatest coupley moment was at the 2001 American Music Awards, when their matching denim outfits went down in fashion infamy. So, perhaps Katy Perry tried to prove that such greatness could, indeed, be repeated. At the 2004 VMAs, she and her date, hip-hop star Riff Raff, donned head-to-toe denim in honor of the 00s’ favorite pop pair.

Give ’em shell

If you watched the VMAs in 1999, there’s no way you don’t remember Lil’ Kim’s outfit. Never one to be overdressed, the hip-hop queen strode the red carpet with a tiny shell appliqué over one half of her chest. It gave her just enough coverage for a cable TV award show.

Two-piece for a newly minted one-piece

Mariah Carey was fresh from her divorce from Tommy Mottola when she attended the 1997 VMAs. With her simple, sultry fashion choice, though, the conversation changed, leaving everyone talking about her revenge outfit instead. And while it’s hard to believe after seeing some of the other entries on this list, Carey’s two-piece was actually regarded as being among the most controversial gowns of the decade.

Sultry Spears

It’s no secret that Britney Spears is a VMAs icon. She’s danced with snakes, kissed Madonna and taken home Moonman after Moonman. That’s why we love her muted look from the 1999 ceremony. The sheer fabrics, feathered cuffs and sequined skirt make a statement, for sure. But on the person who’s going to smooch the Queen of Pop on a public stage? Well, it’s actually fairly demure.

Branding via ballgown

When she walked the red carpet at the 2001 VMAs, Macy Gray had something to tell the world: she had a new album coming out. But rather than speaking those words to the press and to the public, she decided to just… wear them. Yep, as you can see, her dress straight up told everyone to expect a new album and when. We guess that’s what you had to do before social media...

Material girl

It’s hard to believe, but this was the first time Madonna wore something that really got people talking. Yes, the famous “Boy Toy” belt wrapped around her white, sheer frock created even more buzz around the pop star, who was making her VMAs debut that night in 1984.

Curves on the carpet

On the list of most iconic VMAs looks ever, you’ll always find Rose McGowan and Marilyn Manson walking into the 1998 event. The actress’ dress – if you can even call it that – left her completely exposed at the front and, well, more or less the same from behind. Her then-beau, on the other hand, chose to pair his cherry-red locks with a matching leopard-print jacket. Me-ow.