With the 68th Grammy Awards just around the corner, the excitement isn’t limited to who will take home the gilded gramophone. For many viewers, the red carpet is just as important, especially when it comes to outfits that push boundaries and leave people talking for years to come.
And if there’s one look that still dominates conversations ahead of this year’s ceremony, it’s Biana Censori’s jaw-dropping appearance at the 2025 Grammys.
Censori arrived with her husband, Kanye West, wearing a large black fur coat. A few moments later, she dropped the coat in front of the cameras, revealing a completely sheer mesh dress underneath.
Apparently, her ensemble had no lining, no coverage, and no attempt to hide anything. The moment quickly took over social media and, for many, overshadowed the night’s actual award winners.
Image credits: Getty/Jon Kopaloff
Several netizens called it performance art or a visual reference to Ye’s Vulture era; others felt it crossed a line.
“This isn’t fashion,” one social media user wrote, while another said the moment made them uncomfortable.
Despite the backlash, Ye doubled down on X, praising his wife. He called her “smart, talented, brave, and hot.”
“People asked how your mother feels. You don’t know my mama.” He later claimed the stunt helped them “beat the Grammys,” referencing the spike in searches for Censori’s name.
As unsettling as the moment was, it didn’t happen in a vacuum. The Grammys have always been a place where artists take risks with their fashion choices. Over the years, stars like Lady Gaga, Cardi B, Nicki Minaj, Miley Cyrus, Doja Cat, and others have all turned the award function red carpet into a headline-worthy moment.
As the 2026 Grammys approach on February 1, we’re looking back at 30 of the wildest, boldest, and most unforgettable Grammy outfits of all time.
#2 Miley Cyrus, 2024
Less than an hour before picking up her first-ever Grammy for Best Pop Solo Performance for Flowers, Cyrus hit the red carpet in a custom Maison Margiela look that immediately got people talking.
The singer wore a sculptural, barely-there gown made entirely of gold safety pins. Inspired by John Galliano’s “Susy Sphinx” collection from 1997, the dress hugged her body in intricate patterns, paired with Margiela Tabi heels.
However, viewers got instantly distracted by her hair, and not in a good way.
Social media quickly zeroed in on the look as a whole, as one wrote, “Look like she stuck her finger in a plug socket and her hair stood on end lol.”
“Hate the hair on her. Aged her big time,” another wrote.
“Please, someone arrest her hairdresser,” a third joked.
Others were less amused, with one saying, “Well, she deserves something, but certainly not this outfit,” while another added, “Don’t like that look on her.”
The singer wore a sculptural, barely-there gown made entirely of gold safety pins. Inspired by John Galliano’s “Susy Sphinx” collection from 1997, the dress hugged her body in intricate patterns, paired with Margiela Tabi heels.
However, viewers got instantly distracted by her hair, and not in a good way.
Social media quickly zeroed in on the look as a whole, as one wrote, “Look like she stuck her finger in a plug socket and her hair stood on end lol.”
“Hate the hair on her. Aged her big time,” another wrote.
“Please, someone arrest her hairdresser,” a third joked.
Others were less amused, with one saying, “Well, she deserves something, but certainly not this outfit,” while another added, “Don’t like that look on her.”
Report
18points
#4 Chappell Roan, 2025
Chappell Roan made sure her Grammy debut wouldn’t be forgotten. Arriving for the first time as a nominee in six major categories, the Pink Pony Club singer stepped onto the 2025 red carpet in a vintage Jean Paul Gaultier couture gown from 2003.
The pale blue and mustard tulle dress featured an Edgar Degas-inspired ballerina print and was decorated with a nest-like arrangement of sticks and blue flowers.
Online reactions were as entertaining as her ensemble. One wrote, “I thought she had lovingly crafted one out of paper.”
Another summed it up perfectly, “It’s bad fashion done very well.”
Others couldn’t unsee the details, with comments like, “Her hair thing looks like shredded mozzarella,” and “I thought she had spaghetti on her head.”
The pale blue and mustard tulle dress featured an Edgar Degas-inspired ballerina print and was decorated with a nest-like arrangement of sticks and blue flowers.
Online reactions were as entertaining as her ensemble. One wrote, “I thought she had lovingly crafted one out of paper.”
Another summed it up perfectly, “It’s bad fashion done very well.”
Others couldn’t unsee the details, with comments like, “Her hair thing looks like shredded mozzarella,” and “I thought she had spaghetti on her head.”
Report
10points
#10 Ceelo Green, 2017
CeeLo Green has never exactly blended into a red carpet, but at the 2017 Grammys, he took things to a whole new level.
Arriving in his then-new musical persona, Gnarly Davidson, the performer stepped out in a full head-to-toe metallic gold outfit that immediately stole the spotlight.
The structured, armor-like look featured exaggerated shoulders, a high collar, and a matching helmet, giving off everything from sci-fi villain to fantasy character energy.
The outfit left social media viewers in splits as one wrote, “Ceelo had a Samsung explode in his face, then turned into an iPhone.”
“CeeLo Green lookin like he just killed all the Power Rangers,” another wrote.
“This guy is trying WAY too hard to be the center of attention,” someone commented bluntly.
Others couldn’t get past the sheer absurdity, with one admitting, “I can’t stop laughing irl, imagine wtf people at the Grammys were thinking.”
Another added, “He also looks 4 feet tall… the more you stare, the more you laugh.”
Arriving in his then-new musical persona, Gnarly Davidson, the performer stepped out in a full head-to-toe metallic gold outfit that immediately stole the spotlight.
The structured, armor-like look featured exaggerated shoulders, a high collar, and a matching helmet, giving off everything from sci-fi villain to fantasy character energy.
The outfit left social media viewers in splits as one wrote, “Ceelo had a Samsung explode in his face, then turned into an iPhone.”
“CeeLo Green lookin like he just killed all the Power Rangers,” another wrote.
“This guy is trying WAY too hard to be the center of attention,” someone commented bluntly.
Others couldn’t get past the sheer absurdity, with one admitting, “I can’t stop laughing irl, imagine wtf people at the Grammys were thinking.”
Another added, “He also looks 4 feet tall… the more you stare, the more you laugh.”
Report
5points
#13 Annie Lenox, 1995
Back in 1995, Annie Lennox reminded everyone that the Grammys red carpet doesn’t always have to take itself seriously.
The singer showed up in a black-and-white latex French maid outfit complete with sheer stockings, towering dominatrix boots, and Minnie Mouse ears on top.
Lennox later explained that the look was very much intentional. “What else is a girl going to wear to the Grammys?” she quipped at the time.
"It was an ironic statement on my part — Minnie Mouse is a female cartoon character, partly innocent and partly Disney corporate. It summed up how I felt about the music industry at the time,” she told The Hollywood Reporter.
Looking back, not everyone knew what to make of it as one user questioned, “Annie Lennox baby, what are u doing?”
The singer showed up in a black-and-white latex French maid outfit complete with sheer stockings, towering dominatrix boots, and Minnie Mouse ears on top.
Lennox later explained that the look was very much intentional. “What else is a girl going to wear to the Grammys?” she quipped at the time.
"It was an ironic statement on my part — Minnie Mouse is a female cartoon character, partly innocent and partly Disney corporate. It summed up how I felt about the music industry at the time,” she told The Hollywood Reporter.
Looking back, not everyone knew what to make of it as one user questioned, “Annie Lennox baby, what are u doing?”
Report
3points
#16 Toni Braxton, 2001
At the 2001 Grammys, Braxton proved that sometimes less fabric really does more damage. The singer stepped out in a barely-there white halter gown by Richard Tyler.
Her dress featured a plunging neckline, a completely open back, and two sky-high slits that left very little to the imagination.
Braxton later admitted she knew exactly what she was doing, explaining she wanted to go risqué before settling down.
"I decided that before I got married and had babies, I'd wear this,” per US Weekly.
While the moment made history, the internet did not love the execution.
“She is amazing, but what a terrible dress,” one person commented.
Another joked, “I thought she was only wearing long tissue.”
Her dress featured a plunging neckline, a completely open back, and two sky-high slits that left very little to the imagination.
Braxton later admitted she knew exactly what she was doing, explaining she wanted to go risqué before settling down.
"I decided that before I got married and had babies, I'd wear this,” per US Weekly.
While the moment made history, the internet did not love the execution.
“She is amazing, but what a terrible dress,” one person commented.
Another joked, “I thought she was only wearing long tissue.”
Report
2points
#17 Nicki Minaj, 2012
At the 2012 Grammys, the rapper arrived in a custom red Versace robe that looked part nun’s habit, part high-fashion Little Red Riding Hood.
The flowing satin gown featured a giant embroidered Medusa head on the skirt. She took things a step further by arriving with an escort dressed as the Pope, instantly turning the red carpet into a visual moment.
She paired it with red gloves.
Social media quickly shared their reactions with one writing, “All the girls during this time were very controversial with their religious moments and illuminati moments.”
“It's giving Roman Holiday from Shein,” wrote another,
The flowing satin gown featured a giant embroidered Medusa head on the skirt. She took things a step further by arriving with an escort dressed as the Pope, instantly turning the red carpet into a visual moment.
She paired it with red gloves.
Social media quickly shared their reactions with one writing, “All the girls during this time were very controversial with their religious moments and illuminati moments.”
“It's giving Roman Holiday from Shein,” wrote another,
Report
1point
#18 Taylor Swift, 2021
Taylor Swift’s 2021 Grammys look was pure Folklore fantasy. The singer arrived in a custom Oscar de la Renta mini dress covered head to toe in pressed floral appliqués.
Her dress quickly became one of the most talked-about looks of the night, especially after a seam rip appeared under her arm. Swift handled the minor wardrobe malfunction like a pro as she smiled through photos.
She completed her look with a matching face mask, baby pink Christian Louboutin heels, and Cathy Waterman jewelry.
Online users had thoughts with one writing, “If only she had done a photo shoot in a field with this thing.”
Others saw home décor potential instead, joking, “Hear me out… pillows,” followed by, “Like couch pillows or decorative pillows,” and, “Tbh I think it would make beautiful pillows.”
Her dress quickly became one of the most talked-about looks of the night, especially after a seam rip appeared under her arm. Swift handled the minor wardrobe malfunction like a pro as she smiled through photos.
She completed her look with a matching face mask, baby pink Christian Louboutin heels, and Cathy Waterman jewelry.
Online users had thoughts with one writing, “If only she had done a photo shoot in a field with this thing.”
Others saw home décor potential instead, joking, “Hear me out… pillows,” followed by, “Like couch pillows or decorative pillows,” and, “Tbh I think it would make beautiful pillows.”
Report
1point
