40 Of The Most Outrageous Grammys Wardrobe Choices Ever

It’s red-carpet time again, and celebrities everywhere are quietly freaking out about what they’ll wear to the awards ceremonies. Except there’s often a “how” and “why” in there as well, as these pics from the Grammy red carpet demonstrate. Get ready for some of the most fabulous – and astonishingly bad – fashion you’ve ever seen…

40. Macy Gray – 2001

Macy Gray struck a win for casual dressers everywhere when she arrived at the 2001 Grammys wearing pretty much just jeans and a T-shirt. The latter garment read “Goofy” across the front, which somehow made the ensemble even more endearing. You won’t get many other artists trying the same thing, though.

39. Noah Cyrus – 2021

Turns out that a penchant for outrageous fashion might be genetic. Miley Cyrus’ little sister Noah turned up to the 2021 Grammys in a spectacular statue-like ivory Schiaparelli Couture gown. She loved it so much she literally cried while talking about it to the press on the red carpet. Same, Noah, same.

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38. Nicki Minaj – 2012

Nicki Minaj went full-on weird at the 2012 Grammy Awards. She channeled religious imagery and wore a crimson Versace hooded cape featuring the label’s Medusa head logo emblazoned on the front. That wasn’t even the strangest part, though. As her “date” she brought along an older man dressed as… the Pope. Yes, really.

37. M.I.A. – 2009

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Singer M.I.A. was pregnant at the time of the 2009 Grammys, but she wasn’t about to let that stop her! She wore this wacky polka-dot bikini-like outfit which showed off her massive baby bump. And she performed on stage as well. Incredibly, she gave birth to a little boy mere hours after doing the show.

36. Toni Braxton – 2001

There’s a fine line between wearing a revealing dress and just plain showing off your underwear. Unfortunately, Toni Braxton was on the wrong side of that line in 2001. She wore this white Richard Tyler-created… thing on the Grammys red carpet. Alas, it was eye-catching for all the wrong reasons.

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35. Harry Styles – 2021

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Harry Styles almost broke the internet when he wore a snazzy Clueless-inspired suit and feather boa combo to the 2021 Grammys. Even Alicia Silverstone herself praised the look via Instagram! And unsurprisingly, Styles topped a lot of “best dressed” lists that year.

34. Katy Perry – 2011

To be fair, Katy Perry’s dress for the 2011 Grammys was fairly normal. It was a Giorgio Armani number encrusted with Swarovski crystals. But what made it weird was the fact that she also had a pair of feathered angel wings attached to her back. Perry clearly loves the accessory, as she wore some even more eye-catching ones at the Met Gala seven years later.

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33. Mary J. Blige – 1996

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Animal print was big in the ’90s, but perhaps no one went further with it than Mary J. Blige at the 1996 Grammy Awards. She wore nothing but leopard print – right from the hair down to her shoes. Meanwhile, sunglasses and black gloves topped off the look. She won an award that night, too: Best Rap Performance by a Duo or Group.

32. Sasha Gradiva – 2012

Believe it or not, someone once came to the Grammy Awards decked out in automatic weapons. That was Russian singer Sasha Gradiva, and she caused quite a stir. No one was quite sure why she did it, but in 2016 she clarified to Vice magazine that it was to protest against gun violence.

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31. Kimbra – 2013

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Kimbra wore a sugary sweet silk tulle dress designed by Australian designer Jaime Lee to the 2013 Grammys. You might not be able to see everything on first glance, but there’s a lot on this gown – beads, crystals and two kilos’ worth of pearls. Lee told Vogue magazine after the event, “I couldn’t even tell you the amount of hours that has gone into the dress. My hands are all blistered from the hand-sewing.”

30. Madonna – 2015

As many of you know, Madonna rarely disappoints when it comes to extreme fashion. For the 2015 Grammy Awards the Queen of Pop wore what could only have been described as a matador outfit – complete with fishnet tights and knee-high boots. She was 56 years old at the time, but let’s face it, she’s never let age stand in the way.

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29. Lady Gaga – 2010

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Lady Gaga really is the queen of outrageous fashion choices. And by the time of the 2010 Grammys everyone was waiting with bated breath to see what she’d wear next. The star didn’t disappoint – turning up in a solar-system-inspired Giorgio Armani Privé dress and carrying a strange spiky gadget.

28. Charli XCX – 2015

Alas, Charli XCX’s 2015 Grammys ensemble drew unfavorable comparisons to the Easter Bunny. The furry shawl and the various shades of pink didn’t help matters there. But all the same, she knew what she was doing. Charli even announced to the media on the red carpet, “I hate boring fashion!”

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27. CeeLo Green – 2017

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CeeLo Green pulled out all the stops for the 2017 Grammys. He sent the whole internet into a state of shock when he arrived dressed as, well, some sort of strange gold robot. He was actually only on the red carpet for a few minutes, but that didn’t stop memes aplenty popping up. Before long he had been compared to C3PO, a Golden Snitch and a Ferrero Rocher.

26. Sheryl Crow – 2002

Sheryl Crow’s 2002 Grammys outfit ended up being remembered for all the wrong reasons. She wore a short suede romper which showed a little too much flesh, and over that the musician donned a floor-draping blue duster coat. Also, don’t forget the matching boots! It was very ’00s, but whether that’s a good thing or not is up to you.

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25. Joy Villa – 2015

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If you want to get your name out there, wearing a spectacular outfit at the Grammys is a good place to start. That’s what Joy Villa did at the 2015 ceremony, and how! She wore a dress along with a hat that was constructed entirely out of orange plastic construction fencing. In fact, only some strategically placed tape spared her blushes.

24. Taylor Swift – 2021

Taylor Swift came dressed as an entire flowerbed for the 2021 Grammy Awards, and it actually looked really good on her! The gown was by Oscar de la Renta – only $8,990, according to People – and the jewelry was from Cathy Waterman. It was a pretty good night for Swift since she won her third Grammy at the ceremony and became the first woman ever to do so.

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23. Annie Lennox – 1995

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Annie Lennox came to the 1995 Grammys… Wearing mouse ears? Yes, she really did. And the star explained her reasons to The New York Times newspaper that year. She said, “I think Mickey Mouse is very sinister. My children love him, all children love him, but Mickey Mouse is big because of dollars.” Surely the presence of the bow made her Minnie Mouse, though?

22. Amy Lee – 2004

Before the 2004 Grammys aired The New York Times newspaper reported on nominee Amy Lee’s chosen dress. Apparently, it “[wrapped] around her like a mummy – giving the effect of a corpse and an angel.” That turned out to be a pretty accurate description in the end. And yep, she herself designed it, though it was actually put together by Japanese creator H. Naoto.

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21. Priyanka Chopra – 2020

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Priyanka Chopra wore an ivory Ralph & Russo gown to the 2020 Grammys – one which coordinated perfectly with the outfit her husband Nick Jonas wore. The plunging neckline drew some comment, though. Some fashion commentators thought she was trying too hard to imitate J-Lo’s famous 2000 Grammy dress.

20. Jennifer Lopez – 2000

Imagine it’s the new millennium and you’re about to pull off a Grammys outfit that people will remember for decades to come. Well, that’s exactly what happened to Jennifer Lopez in February 2000 when she wore a barely there green patterned Versace dress. And according to executive chairman Eric Schmidt, the subsequent furore resulted in the creation of Google Image Search!

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19. Lady Gaga – 2016

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Lady Gaga paid tribute to David Bowie at the 2016 Grammys ceremony. She wore a blue gown from Marc Jacobs and a pair of incredibly high platform shoes, but it was the hair and makeup that really made the look. The general consensus among fans and commentators was that Bowie himself would have approved.

18. Alicia Keys – 2002

Alicia Keys just wore everything at the 2002 Grammy Awards. There were embroidered jeans, a sparkly turquoise hood and even tiny Swarovski crystals dotted around the singer’s eyes. Keys told People magazine at the time, “Out of the box is my theme tonight.” Yep, she definitely wasn’t kidding.

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17. Dencia – 2016

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Singer Dencia wore a truly remarkable outfit to the Grammys in 2016. It was a bright pink onesie covered in crosses, sparkles and a variety of Hello Kitty plushies. She topped off the look with some matching pink glasses and hair bows in – you guessed it – pink. She made plenty of “worst dressed” lists, but you can’t deny it was something different.

16. Future Man – 2009

Five-time award winner Future Man wore what can only be described as a fabulous pirate outfit to the 2009 Grammy Awards. Not everyone was a fan, though. Fashion blogger and stylist Emmi Sorokin wrote at the time, “What do you get when you combine a pirate, a poet, the Highlander Prince, and a waiter from a Chinese noodle house? Apparently Future Man at the Grammys.”

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15. Doja Cat – 2021

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Doja Cat made a splash at her first Grammys by wearing an incredible plunging-neckline feathers-and-leather dress. On the red carpet she told E! News, “I like something that’s out there. I have been very toned down lately. This is like something I have always wanted to do.” Fair enough.

14. Sisqo – 2000

Sisqo really unleashed the dragon during his appearance at the 2000 Grammys. He wore an incredible red leather creation which had an intricate design of said fire-breathing monster on the leg. Don’t forget the matching red gloves, sunglasses and the spiky bracelet! Sisqo himself seemingly forgot his shirt, though.

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13. Nicki Minaj – 2011

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Nicki Minaj came to the 2011 Grammys dressed as… the Bride of Frankenstein? Or Cruella de Vil maybe? She was wearing entirely animal print, after all. On the red carpet the Best Rap Performance nominee explained that the outfit was by Givenchy, and the hair was all her own.

12. Florence Welch – 2013

Singer Florence Welch wore a tight-fitting green Givenchy gown on the 2013 red carpet. Apparently, she was going for some sort of reptile-inspired look, since the dress had lizard-like spikes on it and she accessorized with snake jewelry. Yes, there were Godzilla jokes on social media, but Welch herself seemed happy to be wearing it.

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11. Bootsy Collins – 2004

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Leopard print appears to be a pretty popular choice on the Grammys red carpet. In 2004 – a year that was considered quite a bland one for Grammys fashion – Bootsy Collins wore what might have been an entire leopard under a leather coat. And then there were the sunglasses, which surely he must have had trouble seeing out of!

10. Rihanna – 2015

Rihanna’s pink dress was considered one of the standouts on the red carpet in 2015. It was a massive, frilly, cupcake-like creation that delighted almost everybody. The star told Ryan Seacrest upon arrival that the gown was designed by Giambattista Valli and she “just fell in love with it.” Can you blame her?

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9. Phoebe Bridgers – 2021

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Phoebe Bridgers – who was nominated for four awards – wore a skeleton outfit to the 2021 Grammys. To be fair, skeletons are her signature and this was a particularly cool dress. It was designed by Thom Browne and featured pearls, beads and crystals. Of course, it was a weird look, but her fans went wild for it.

8. Lil Nas X – 2020

Lil Nas X managed to dazzle everyone in 2020. He arrived on the Grammys red carpet wearing an outrageous hot pink gold-studded cowboy outfit with mesh underneath – a creation from Versace. Billboard magazine declared at the time, “Lil Nas X has become one of music’s coolest young fashion stars, thanks to his love for vibrant and abstract interpretations of the classic cowboy look.”

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7. Cardi B (2019)

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Cardi B pulled out an absolute showstopper in 2019. She wore what was basically a “human pearl” costume – the dress served as the shell that she was emerging from. It was an archive piece from Mugler Couture, and according to the Los Angeles Times, it was only the second time in 25 years that the company had let a celeb wear one of those.

6. Imogen Heap – 2007

Imogen Heap didn’t win Best New Artist at the 2007 Emmys, but it’s probably fair to say she won weirdest red carpet outfit. It was, uh, pond themed – complete with grass in her hair and a toy frog in her hand. Heap told reporters, “A fabulous designer from Los Angeles got in touch with me via MySpace asking me if she could make my Grammy dress, and this is what happened.” She added that the frog was named Gary.

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5. Chika – 2021

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Some of the outfits at the 2021 Grammys had to be a little different due to the pandemic and the need to wear masks. Though many attendees worked them into their attire – including first-time nominee Chika. She wore a spectacular custom-made Nike sweatsuit in pastel colors, and the mask was an intrinsic part of it.

4. Janelle Monae – 2016

Janelle Monae absolutely loves to dress in monochrome, and she wore it to full effect at the 2016 Grammy Awards. She had on a stunning lace and velvet creation from the Jean Paul Gaultier Fall 2015 Couture collection matched with a pillbox hat. General consensus in the media was that only she could have made something like that work.

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3. Alicia Keys – 2004

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Wearing jeans on the red carpet is a major risk, and unfortunately it was one that didn’t quite work for Alicia Keys in 2004. The singer didn’t just wear jeans, she had a sort of half-dress over the top which looked a bit bizarre. And then there was the denim cuff on one arm. Yep, it was a curious mishmash which didn’t go down too well.

2. Billy Porter – 2020

Billy Porter went incredibly extra on the 2020 red carpet and fans loved him for it. The actor and fashion icon wore not only a bejeweled blue jumpsuit but also a motorized hat that moved a fringe of sparkling crystals in and out of his face. His platform boots and his spider-shaped bracelet were likewise covered in bling. It was bizarre and amazing in equal measure.

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1. Lady Gaga – 2011

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The weirdest Grammys outfit of all time was only an outfit in the loosest sense of the word, but wow. Lady Gaga traveled the 2011 red carpet in an egg before “hatching” from it to perform “Born This Way” on stage. The star claimed to Ryan Seacrest that year that she spent 72 hours in all inside the “vessel.” The things celebs do for fashion!

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