40 Iconic Grammys Red Carpet Looks We Still Think About — For Better or Worse
It's almost time for the Grammys 2025, and there's no better way to build anticipation than a trip down memory lane. Each year, the Grammy Awards bring together the top artists in the game for music's biggest night. On top of music galore, the Grammys ceremony allows the artists in attendance (including nominees and performers) to have some extra fun when it comes to fashion as they push the limits and shock photographers in whichever way they desire.
While we're excited to see who will be taking home the awards on Sunday night, we’re also excited for the red-carpet fashion. Every year, there's at least one look that shakes us to our core — yes, we're still not over BTS's matching tuxedos or Troye Sivan ripping his nipple piercing on camera.
The Grammys give our favorite artists the space to express their true creative selves, and over the years, many have done so in museum-worthy and wild ways. Remember Lady Gaga showing up in an egg? Or CeeLo Green looking like a gold statue? Well, if you need a refresher, here are 40 of the most iconic (and outrageous!) Grammys red carpet outfits of all time.
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Cher's Butterflies
In 1974, Cher stunned at the Grammy Awards wearing a large 1974 pin in her hair and a matching midriff-bearing ensemble.
Ron Galella/Getty Images2/40Dolly Parton's Barbie Moment
In 1977, for the 19th Annual GRAMMY Awards, Dolly Parton was already a pioneer of the full-pink look — and can we talk about the volume of that 'do?
Ron Galella/Getty Images3/40Grace Jones's Issey Miyake Serve
Grace Jones attended the Grammys in 1983 with Rick James to present Marvin Gaye with the award for Best R&B Vocal Performance, and she did so wearing a sculptural leather dress complete with a matching headpiece by Issey Miyake. The literal embodiment of iconic.
Barry King4/40Cyndi Lauper’s Tropical Rainbow Dress
Back in 1984, before Lady Gaga was here to bless us, Cyndi Lauper was making headlines at every awards show with her out-there fashion looks, and the Grammy Awards that year were no exception. Lauper's tropical vacation gown completely fit her personal, outrageous style, and we truly loved to see it.
Images Press/Getty Images5/40En Vogue
In 1991, En Vogue shut down the Grammys red carpet wearing 'fits made from traditional African fabrics. (The Grammys coincide with BHM after all!)
6/40Celine Dion's Sheer Knit
Celine Dion attended the 35th Annual Grammy Awards in 1993 wearing a black sheer knit dress that let her matching thong peeking out.
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Selena's Big Night
In 1994, Selena attended the 36th Annual Grammy Awards at Radio City Music Hall in New York City, wearing a stunning white dress by Lillie Rubin that became an instantly recognizable image of the late star. She picked up the award for Best Mexican-American Album that night, her only award until she was posthumously honored with a lifetime achievement award in 2021.
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TLC Matching in White
Chili, Left Eye, and T-Boz (a.k.a. TLC) also made their presence known rocking matching white fits at the 38th Annual Grammy Awards in 1996.
Steve Granitz9/40Mary J. Blige's Cheetah Dream
Also in 1996, Mary J. Blige made sure to make a statement with a full-cheetah-print look and sunglasses.
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Jennifer Lopez’s Versace (and Google-Search-Creating) Dress
J.Lo's iconic green dress was the dress that inspired a million searches! At the 2000 Grammy Awards, J.Lo’s deep-plunge green Versace dress blew so many people away that it literally created Google Images. What's more, in 2020, two decades later, it still is the top searched look from the Grammys red carpet. Talk about iconic!
Jim Smeal/Getty Images11/40Britney Spears's Winter Wonderland
Also in 2000, Britney Spears made classic look easy in a Randolph Duke gown and Oscar de la Renta fluffy stole.
David McNew12/40Toni Braxton's Take on Cutouts
In 2001, Toni Braxton rocked a statement cutout white dress designed by Richard Tyler that left very little to the imagination to pick up the gramophone for Best Female R&B Vocal Performance.
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Destiny's Child in Matching Emerald
No one does coordinating looks quite like Destiny's Child. The trio matched in emerald green at the 2001 Grammys in looks designed by Tina Knowles, Queen B's mother herself.
Frederick M. Brown/Getty Images14/40Lil' Kim's Motomami Moment
Before Rosalía's Motomami era, we had Lil' Kim at the 2002 Grammys.
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Missy Elliot's Vie en Rose
At the 2003 Grammy Awards, Missy Elliot wore the most Missy Elliot 'fit ever: a pink adidas tracksuit with Superstar sneakers and socks, and a Kangol hat — all matching.
Frank Trapper/Getty Images16/40Imogen Heap’s Frog-Inspired Ensemble
At the 2007 Grammy Awards, Imogen Heap showed up looking like a, well, like a swamp. Her black dress was embellished with water lilies and leaves, and in her hand laid a little frog. Another look that we can't erase from our minds — for whatever reason!
Photo: GABRIEL BOUYS/AFP/Getty Images17/40Lady Gaga's Celestial 'Fit
This wouldn’t be an iconic Grammys slideshow without this 2010 Mother Monster moment! Stepping out with bright yellow hair and a custom Giorgio Armani gown, Gaga stole the show before it even began.
Frank Trapper/Getty Images18/40Lady Gaga’s Egg Entrance
Lady Gaga has long been pushing the limits of fashion — from the MET Gala to the VMAs and, of course, the Grammys. Back in 2011, Gaga showed up to the awards inside a faux egg. To top it all off, she burst from the egg during her performance onstage. Talk about iconic and outrageous!
Frank Trapper/Getty Images19/40Katy Perry Looking Like an Angel
The same year that Gaga had her egg moment, Katy Perry showed up to the awards looking like an angel that just came down from heaven.
Jon Kopaloff20/40Sasha Gradiva Is Battle-Ready
Talk about being guarded! At the 2012 ceremony, Sasha Gradiva came in a beautiful light-pink gown styled with…metal armor and a bionic arm. Comments? Many, but we'll save them.
Photo: Jon Kopaloff/FilmMagic21/40Adele's Pretty in Pink Meets Flower Power
Adele’s ladylike Valentino dress from 2013 was totally different than your average Grammys ensemble — and that’s exactly what helped her stand out. It just goes to show you should never underestimate the power of a pretty dress and a classic cat eye.
Photo: Jason Merritt/Getty Images22/40Maddie Ziegler and Sia's Matching Wigs
Maddie Ziegler has performed in two of Sia’s music videos, so it was no real surprise that they showed up together at the 2015 Grammys. But that didn’t make their custom Armani Privé suits (and, ahem, those wigs!) any less impactful.
Photo: Jon Kopaloff/FilmMagic23/40Rihanna Was Tickled Pink
This Giambattista Valli dress launched a thousand memes the second Rihanna hit the red carpet in 2015. If that’s not iconic, we don’t know what is.
Photo: Jason Merritt/Getty Images24/40Taylor Swift's Stunning Dress
With a shimmering Elie Saab dress, matching jewelry, and fuchsia sandals, Taylor’s look in 2015 was a win from head to toe.
Photo: Jason Merritt/Getty Images25/40Miley Cyrus's LBD (Long Black Dress!)
It’s hard to be surprised by anything Miley Cyrus wears at this point (giant faux furs, sequins, stickers on her face — we’ve seen it all!), but this cutout, backless Alexandre Vaulthier dress was seriously unexpected. She kept her face super fresh and bare and simply slicked her hair back, giving this minimal look major impact — back in 2015 and in 2024.
Photo: Jon Kopaloff/FilmMagic26/40Charli XCX Suited Up
Charli XCX marches to the beat of her own drum, so any old dress would not do. In 2015, this white Moschino suit looked sleek and different — perfect for the budding pop icon.
Dan MacMedan/Getty Images27/40CeeLo Green's Gold Transformation
At the 2017 awards, CeeLo Green showed up looking so expensive, some were ready to melt him down into jewelry. That’s because he came dressed as a gold statue. Just a fashion look or is he a missing Avenger? The world may never know.
Dan MacMedan/Getty Images28/40Cardi B’s Oyster Dress
Cardi B stole the red carpet spotlight at the 2019 Grammy Awards. She truly took viewers by surprise when she showed up in this oyster/pearl/clam-inspired dress that had us singing “Under the Sea” all night long. While it might not be for everyone, it's certainly a look to be remembered!
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Lil Nas X's Barbiecore Cowboy Look
Lil Nas X was years ahead of the Barbiecore trend when he donned this bright pink cowboy ensemble from Versace in 2020.
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Ariana Grande's Princess Dress
There's no such thing as too much tulle! Ariana Grande proved that at the 2020 Grammy Awards, where she wore a layered gown from Giambattista Valli Haute Couture. She styled the dress with her signature high-ponytail and opera gloves, giving the look a regal feel.
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Megan Thee Stallion's Orange Gown
Leave it to the hot girl coach to teach us how to wear a bold color. Megan Thee Stallion rocked a bright orange dress complete with a bow to the 2021 Grammy Awards.
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Donatella Lipa — or is it Dua Versace?
While Lipa opted for a bubblegum pink gown the year prior, she went for a darker alternative in 2022. Juxtaposed by newly debuted platinum blonde hair, the singer donned a black gown, layered with a leather harness and gold chains. She did, however, stick with her beloved Versace.
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Billie Eilish's Illusion
Is it a cape? Is it a blazer? Is it a dress? We're still tying to crack the code, but we do know Billie Eilish's 2022 Grammys look from Rick Owens lives in our heads rent free.
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Harry Styles' Bedazzled Jumpsuit
Harry Styles is known for his fun fashion sense, but this look from EGONLAB took his style to another level at the 2023 Grammys. The “As It Was” singer lit up the red carpet with his colorful jumpsuit covered in Swarovski crystals.
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Miley Cyrus's Safety Pinned Serve
Miley Cyrus was hands down the celebrity that made the most significant statement at the 2024 Grammys. The star, who won her first Grammy that night, stunned in an intricate see-through dress made of golden safety pins from Maison Margiela, which she, of course, paired with Tabis. Talk about iconic.
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Miley Cyrus's 2002 Bob Mackie
If you thought that was the only serve that Cyrus had for the night, think again. For her performance, the star changed into a Tina Turner-inspired gown crafted by Bob Mackie in 2002, throwing it back to the golden days.
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The Triple Threat of boygenius
By now, you'd have gathered we love a matching suit moment, and Phoebe Bridgers, Lucy Dacus, and Julien Baker of boygenius gave us that with a twist at the 2024 Grammys. The trio rocked matching off-white textured Thom Browne suits with a woodgrain-inspired pattern, paired with black shoes and ties. They added a pop of color with a pink flower and Artists4ceasefire pins.
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Caroline Polachek Wears Her Heart on Her Sleeve
Caroline Polachek chose Belgian designer Olivier Theyskens for her memorable Grammys look, donning a gown from 1998 with intricate artery-inspired embroidery.
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Taylor Swift's Black and White Moment
Whether you loved it or hated it, Taylor Swift's 2024 Grammys look was undoubtedly the center of many conversations. The singer's structured Schiaparelli gown was indeed stunning, but many argued that the contrasting black accessories floundered the look. Regardless, she was the talk of the town and made a lasting impression.
