The Most Inappropriate Outfits In Grammys History – Glam

If you tuned into the red carpet at the 2025 Grammy Awards, you know that there was no missing Bianca Censori’s unexpected outfit. Censori, the wife of rapper ye, formerly known as Kanye West, took the so-called “naked dress” trend to a whole new level, wearing a completely see-through one that had us all doing double takes. Now, we’ve all seen the naked dress trend and discussed practical ways to style it — in fact, Ye’s ex-wife, Kim Kardashian, has become a pro at them — but Censori’s version left nothing to the imagination. While there were plenty of worst-dressed celebrities at the 2025 Grammys, there’s no denying that Censori’s look will be remembered for years to come. However, shocking fashion at the Grammys is practically tradition. Before Censori’s barely there moment, the awards show had already seen its fair share of inappropriate, over-the-top, and downright bizarre looks. From costumes disguised as fashion to outfits that revealed way more than we ever asked for (though, to be fair, none quite like Censori’s), the Grammys red carpet has been home to some truly unforgettable style moments. And then there are the red-carpet moments that were so odd they instantly become pop culture history — like when a rapper brought a pope impersonator as their plus-one or when a pop star literally arrived inside of a giant egg. Here’s a look at the most outrageous outfits to ever hit the award show’s red carpet.
At the 2020 Grammy Awards, musician Joy Villa walked the red carpet in a gown that was a major political statement all its own. The dress was a walking billboard in support of President Donald Trump, with his name plastered on the front and the words “Impeached” and “Re-elected” on the back. While musicians making bold fashion statements is a Grammy norm, Villa took things to a whole new level with this ensemble, which was impossible to miss. “I feel like Miss America in this; it’s all couture,” Villa told The Hollywood Reporter on the red carpet before adding, “He’s going to be the first president in history to be impeached and re-elected.”Believe it or not, this wasn’t her first time using fashion to make a pro-President Trump statement. In fact, at this point, it was kind of her thing. In 2017, she showed up in a “Make America Great Again” dress, and in 2019, her Grammys gown featured “Build the Wall” written across the back. When asked whether she’d run her 2020 look by President Trump beforehand, Villa said, “Oh, he’ll be surprised!” She added that she did give Ivanka Trump and the White House a heads-up, saying, “I’m going to wear something to be supportive. I don’t let anyone know the message beforehand.” Gotta keep the suspense, right?The designer behind the controversial dress, Desi Allinger, opened up to The Hollywood Reporter about the inspiration behind the look. “The collar of Joy’s latex dress was inspired by a neckline on a dress by Alexander McQueen, and the coat is inspired by our first lady [Melania Trump] — I just picture her in this,” he said. “So yeah, USA!”
While see-through dresses are practically a red-carpet staple today, back in the early ’90s, rocking a sheer look, especially at a prestigious event like the Grammys, was a bold and rare move. So, when “My Heart Will Go On” singer Céline Dion stepped onto the 1993 Grammys red carpet in a daring black gown that left little to the imagination, many considered it an inappropriate look.The knitted dress gave off major beach-cover-up vibes, but Dion, as always, looked absolutely stunning. That said, the sheer fabric definitely revealed a bit more than what is considered red carpet-friendly. From the front to the back, it was a fashion risk that got people talking. Since then, the look has become iconic and beloved; however, Céline Dion has only continued her stunning transformation, showing that her style is never stagnant. One fan reminiscing on X, formerly known as Twitter, “Thinking of when Celine Dion wore this legendary see-through black dress at the 1993 Grammys.”
When musician Sasha Gradiva arrived on the 2012 Grammys red carpet in a baby-pink gown paired with an eye-catching and controversial machine gun-inspired arm accessory, many found the look inappropriate. The musician may have looked like she was auditioning for yet another sequel to “The Terminator,” but in reality, Gradiva was using fashion to make a bold statement.In 2016, Gradiva opened up to Vice about the infamous outfit. “I traveled to Israel and Palestine. … I saw a lot of women carrying guns,” she explained. “I came back to LA right before the Grammys, and I talked to my creative friends. I was like, ‘I’m going to do something about it.’ So I came up with this ridiculous outfit — it’s technically a wedding dress.” She revealed that the machine gun piece was created by a designer from New York and admitted that her team tried to talk her out of wearing it. However, she stood firm, explaining, “I actually am trying to say something by wearing this outfit. This clashing pink Barbie dress with this machine gun—this is what’s happening in the world. This is what we’re having as humanity right now, and I want to talk about it.” Gradiva ultimately did make a splash, but we’d argue this wasn’t the right venue for it.
In 2012, rapper Nicki Minaj, who used to wear far more out-there looks than she does today, arrived on the Grammy Awards red carpet in a custom red Versace design that looked more like a dramatic robe-cape hybrid — complete with a hood! — than a traditional gown. In fact, some thought the look was nun-inspired —but make it satin and scarlet — while others saw it as a high-fashion Little Red Riding Hood cosplay. Regardless, the skirt featured the ultimate Versace flex: a giant embroidered Medusa head because if you’re going to make a statement, you might as well go all in.While the outfit alone was enough to turn heads, what really stole the show was Minaj’s unexpected plus-one: a man dressed as the pope. This look was peak “church at 4, Grammys at 6, and no time to change” energy.
In 2001, “Just Be a Man About It” singer Toni Braxton took a major fashion risk with a gown by Richard Tyler that had all the drama (and very little material). The white dress featured a daring neckline and two ultra-high slits — if we can even call them that — that pretty much bared it all. With every step, Braxton seemed to be exposing more than was necessary, and it definitely looked like she’d ditched the underwear for this one.”I’ve always gone a little risque with all my other awards [show outfits],” Braxton confessed to People at the time (via Us Weekly). “I decided that before I got married and had babies, I’d wear this.” Well, mission accomplished — her risky look made an impression, but for many, it was an inappropriate one.
Early-aughts fashion was like a chaotic experiment, and while Y2K fashion is back, it’s definitely being styled differently. For many stars, this era was all about taking fashion risks and experimenting with their look, which is why when singer Alicia Keys showed up to the 2002 Grammy Awards in jeans, a white tank top, and a see-through shawl tied across her outfit and head, nobody was exactly shocked. The outfit wasn’t great — it looked like it could be worn to the Kids’ Choice Awards — but it at least showed that some experimental thought went into it. And yes, the musician was rocking sparkly eyelashes — and no, they didn’t help the look.In hindsight, this DIY-inspired fashion moment might just be one of the most inappropriate looks in the award show’s history. The entire outfit looked like it was thrown together in five minutes with supplies from the back of her closet. We think we can all agree that the Grammys deserve a little more prep than that!
Musician Shania Twain made quite the statement when she walked the 2023 Grammys red carpet in a very unexpected look. Put together by stylist Chris Horan, her outfit featured a white, satin pantsuit with black, sequin polka dots that gave off some serious cow-print vibes. While the bold pattern and structure of the pantsuit were already odd choices, add the oversized matching hat and vibrant red hair, and you’ve got a look that screams “cosplay” and not “Grammys-worthy fashion.””This is a London designer. His name is Harris Reed,” Twain revealed on the red carpet (via Glamour). “It was black and white, and I needed a little bit of color,” the “Man! I Feel Like A Woman!” singer explained, referring to her red hair. Well, she definitely got our attention, but that still don’t impress us much.
Goth fashion can definitely work at the Grammys — if it’s done with a glamorous and edgy touch. However, Phoebe Bridgers’ 2021 look was everything but that. The singer arrived at the awards ceremony in a Thom Browne dress that was more Halloween than haute couture, even though the skeleton on it was fully glittered.”I wear a skeleton costume all the time, but one of the reasons I do is because I saw this Thom Browne dress forever ago and thought it was so cool, and I asked for it,” she told E! News on the carpet, adding, “I basically stole it.” Now, don’t get us wrong: We don’t hate this look, but it is more MTV VMAs than Grammys.
Katy Perry’s custom Giorgio Armani dress made from iridescent material was pure perfection, and it would have been totally Grammy-appropriate in 2011 — had it not been for the wings. In fact, the bedazzled bodice and the holographic color of the skirt were so stunning they could’ve easily made Perry one of the best-dressed ladies of the night. But instead, the outfit ended up looking too much like a costume.Now, we’re not sure if the wings were a part of Armani’s design or if Perry or her stylist decided to add them, but one thing’s for sure: The look would’ve been way more Grammy-appropriate without them, as they were giving Victoria’s Secret runway vibes more than a prestigious music ceremony. Of course, Katy Perry is no stranger to inappropriate outfits, having worn quite a few over the years, but we were sad to see this look fall into this category.
The 2000s era was definitely a bold one for fashion, and Black Eyed Peas singer Fergie’s 2004 white, shredded minidress is certainly proof of that. It was passable for a girls’ night out at a beach club, but the biggest night in music deserved a bit more glamour and a lot less shredding.However, Fergie still stands by the look. “I knew I was doing sexy at that point. It’s Dolce & Gabbana,” Fergie revealed to Allure in 2015, over a decade after wearing it. “So I went for it. I’m fine with showing cleavage. It has a good under-the-boob thing, almost like a bathing suit. It held me up!” There’s no denying that the singer could wear a trash bag and look stunning, but the Grammys was definitely not the right place to showcase a look like this.
Madonna’s 2015 Grammy Awards look is definitely one of the celebrity red carpet outfits that went off the rails. The queen of pop wore a Givenchy haute-couture piece full of intricate details that made it bold and edgy. The look, designed by Riccardo Tisci, gave matador energy but in a very sexy way; however, while it screamed “fashion statement,” it didn’t quite scream “Grammy chic.”Now, Madonna’s been in the industry long enough that we might’ve let this costume-like ‘fit slide if it weren’t for the cheeky moment when the back of her skirt lifted too much and revealed her thong to the entire world. That’s the kind of peek we could’ve done without, especially at such a prestigious event. That said, we appreciate a woman who owns her body.
When rap star Doja Cat showed up to the 2024 Grammy Awards red carpet, many of us were left wondering whether she was showing too much on purpose or just, well, not quite getting it right. The star wore a see-through corset dress by Dilara Findikoglu, and let’s just say that half of her nipples were out for everyone to see.While the sheerness of the dress alone was a bold move, the ill-fitted top portion of the corset made the entire look awkward, especially as most of us couldn’t figure out if that was an intentional part of the look or just a fashion misstep that left a few people feeling uncomfortable. Either way, the look made it onto our list of worst-dressed celebs of the 2024 Grammy Awards for these reasons.
If there’s one celebrity who knows how to create a memorable moment, it’s Lady Gaga. So, when the singer arrived at the 2011 Grammy Awards inside of a giant egg, it was instantly clear that this was going to be one for the history books. “This is Nicola, Haus of Gaga: Gaga is in incubation. Tonight’s performance is in collaboration with Hussein Chalayan and House of Mugler. X,” her stylist, Nicola Formichetti, wrote on Gaga’s X, formerly known as Twitter, account. And no, for those who didn’t watch the event live, she didn’t hatch on the red carpet, making this one of the strangest and most committed entrances in Grammys history.”I was in there for about 72 hours,” Gaga revealed to Ryan Seacrest on his eponymous radio show two days after the event (via Today). “It was a very creative experience. It was time for me to really prepare and think about the meaning of the song,” she added, referring to her hit “Born This Way,” which she performed at the awards show for the first time. Now, we’re all for method artistry, but 72 hours inside an egg (sorry, “vessel”)? That’s next-level commitment, even for someone like Lady Gaga who’s known for incredible fashion risks.
Rapper Lil’ Kim hit the 2002 Grammys red carpet in an eye-catching, red motorcycle suit by Chanel. But, of course, this wasn’t your average biker-babe moment — Lil’ Kim’s cropped jacket and bedazzled statement belt took the look from highway to extravagant fashion. To top it off, she carried a matching Chanel helmet, fully committing to the aesthetic.Now, had this been Halloween — or even a more casual awards show like MTV VMAs — this could have been a fun, campy moment, and there’s no denying that she looked stunning. But as we’ve established, the Grammys deserve more than a couture cosplay session. Now, if you want more jaw-dropping celebrity fashion choices, check out the most inappropriate celebrity outfits of 2024.

Source: https://www.glam.com/1783696/most-inappropriate-outfits-grammys-history/