“The More You Stare, The More You Laugh”: 30 Grammys Looks That Sent The Internet Into A Spiral

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.”

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.”

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.”

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?”

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.”

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.”

Harry Styles has never been afraid to dress a little left of center, and at the 2023 Grammys, he fully leaned into that reputation.

The pop star donned a low-cut, chest-baring jumpsuit that sat somewhere between chic fashion experiment and theatrical costume.

Designed by Egonlab in collaboration with Swarovski, Styles ensemble featured a rainbow patchwork pattern covered in more than 250,000 crystals.

The sparkly harlequin-style jumpsuit showed off his chest tattoos. Styled by his longtime collaborator Harry Lambert, the look was paired with white boots, chunky rings, and his signature necklace.

Social media users weren’t exactly convinced by his looks.

“He’s so cute, but I lowkey think he looks like a member of the circus,” one person wrote.

“No, no, no. It’s Pepino, the clown,” another joked.

“It’s a kindergarten quilt,” someone else commented.

Others were more critical, with one saying, “His stylist needs to find a new profession, his outfits are never it.”

Another added, “He puts absolutely no effort into his looks, and his stans pretend he’s breaking barriers. His style was honestly better in One Direction.”

If there’s any celebrity who treats the Grammys like performance art, it’s Lady Gaga. After she arrived at the 2011 ceremony sealed inside a giant egg, no one was exactly surprised.

The oversized “vessel designed by Hussein Chalayan was carried down the red carpet by models in beige latex, which instantly became one of the most bizarre entrances in Grammys history.

Her stylist Nicola Formichetti said that the singer was “in incubation”, preparing for the debut performance of Born This Way later that night.

Surprisingly, Gaga was inside the egg for roughly 72 hours.

"It was a very creative experience. It was time for me to really prepare and think about the meaning of the song,” she told during an appearance on Today.

While it was a stunt of method artistry for Gaga, the internet had other interpretations.

“Why are you inside an egg?” one person asked bluntly.

“I can’t wait until they roll her up on stage to get her awards,” another joked.

“Quick! The egg market is now booming! BUY BUY BUY,” someone else wrote.

Others found a practical upside, with one comment noting, “I must say this is the most ingenious way to avoid talking to the media on the red carpet.”

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,

At the 41st Grammy Awards, Madonna reminded everyone why reinvention is practically her brand.

The singer stepped out in a bold red Jean Paul Gaultier kimono-style outfit while performing at the final Grammys of the 20th century.

Her glossy red ensemble featured dramatic sleeves, a structured waist, and matching red boots.

“I always loved it, but as our society evolves, it’s clear there were some missteps from M in appropriating certain cultures in her work as a white artist. I used to love this, but now I look back and kind of cringe,” wrote one user.