The Grammys celebrate music and the artists who make it—but it’s also become a place for edgy, out-there fashion. Greats including Cher, Dolly Parton, and Lady Gaga have all made the Grammys their red carpet playground, using it to show off their fashion-forward personas.
In the ’90s and ’00s in particular, there was a ton of risk-taking (some of it done without the help of stylists!), but the ’20s have brought us some truly epic couture. Modern-day Grammys fashion ranges from surprising and head-turning to some of the most gorgeous gowns we’ve ever seen—you know, the kind that take hundreds of hours to make. Chances are, there’s at least one gown you recognize on here.
Below, the 32 best Grammys outfits ever.
Billie Eilish
For the sheer “cool” factor, it’s hard to top Billie Eilish in red and black hair and a complementary oversized black outfit. Fun fact: Her Chrome Hearts varsity jacket had “Barbie” embroidered onto it, per InStyle, so her clothes are smart promotion and support, too!
Harry Styles
Harry Styles, constant fashion innovator, gives us a magnificent purple boa atop a fun plaid blazer and preppy vest. Alicia Silverstone noted how much the outfit looked like Cher’s iconic looks from Clueless (plaid jacket and skirt, feather boa, and fun vest) and gave him a shoutout on her Twitter.
boygenius
For their Grammys debut, boygenius wore gorgeous matching white suits, black patent oxfords, and matching pink carnations with a super-sweet touch, per People: “The trio wore the pink carnations as a tribute to musician Elliott Smith who died in 2003 at age 34 by a stabbing.”
Aretha Franklin
Goddess that she was, Aretha Franklin wasn’t always given she credit she deserved for her fashion choices. She was known for her fur coats (often shrugged or thrown off dramatically mid-performance) and her ballgowns always brought the glam. Plus: that bag!!
Jada Pinkett Smith
For anyone who has ever been pregnant, you’ll know that this kind of fashion mastery—a long gown that’s somehow semi-sheer, backless, and glamorous as heck—is reserved for only the best of us. Jada Pinkett Smith is pregnant with Jaden here and somehow looks effortless.
Destiny’s Child
Destiny’s Child helped to popularize the “matching performance outfits,” and these green dresses are the right kind of over-the-top (bonus that they match all those Grammy awards!). I’ve compared them to Poison Ivy costumes before, and I stand by it, but it’s quintessential early ’00s fashion.
Donna Summer
Singing legend Donna Summer also had an enviable red carpet style (the woman knew how to rock some sparkles!). My favorite has to be this all-leopard dress with matching leopard sandals (bonus points for the gold nail polish) that’s shiny, frilly, patterned perfection.
Naomi Campbell
Who doesn’t love ’90s Naomi Campbell on the red carpet? This pop art-inspired bubble dress is a blast and a half and pretty par for the course for her early fashion sense (in the early ’90s, she even wore a dress with Marilyn Monroe and James Dean’s faces on it). Bonus points for the boa!
Dua Lipa
This beaded silver Courrèges dress is somehow sultry and tough (check out those hip cutouts), and Dua Lipa is wearing it instead of the other way round (the Tiffany & Co. jewels help really sell this look). She quite likes this color, and she also debuted a fresh red hair color at the event.
Adele
Adele’s modern style has been a thing of beauty, and this red velvet gown is no exception. For her return to the ceremony after six years, she wore a ruby Louis Vuitton gown and Tiffany jewelry (naturally), and the whole look worked well with her new gold statuette.
Nicki Minaj
This glam red Versace outfit on Nicki Minaj—a hooded robe with a studded face on the front—is sort of a “Red Riding Hood, but scary” vibe to me. Not pictured: She brought an actor dressed as the pope as her date. And he joined her onstage to rap some of her lyrics. Sure?
Rihanna
Normally Rihana can have an edgy style, so this extremely princessy gown is an unexpected delight coming from her. It’s Giambattista Valli, and fashion pundits joked that she looked like she was hiding several people under her skirt, but she said she loved it and that’s all that matters.
Erykah Badu
Erykah Badu has given us many a magnificent headpiece, but her yellow Nefertiti head wrap is an absolute standout. Apparently she also designed this leather patchwork dress herself, and it’s the kind of edgy, unique, truly epic styling that made Badu an underrated style icon.
Billy Porter
If you haven’t seen Billy Porter’s outfit in motion, you owe it to yourself to watch: The hat was remote-controlled, and the crystal fringe could “close” over his face. The look was designed by Scott Studenberg, and Porter tweeted, “Get on my nerves, and the curtain closes!”
Cardi B
Only Cardi B could attend the Grammys looking like she was a pearl erupting out of a clamshell, and the fashion world would respond with, “Yea! That sounds about right!” Cardi B loves couture and button-pushing, and this did both in vintage Thierry Mugler.
Lady Gaga
Lady Gaga has given us a multitude of fashion lewks over the years (including another on this list), but I confess that this simple silver Celine dress is as gorgeous as any we’ve seen on her. Gaga loves expensive jewelry, and this Tiffany collar necklace was no exception.
Taylor Swift
Now this is how you channel Old Hollywood! Taylor Swift is no stranger to Grammys fashion, and it’s the site of some of her greatest gowns, but this Daniel Roseberry for Schiaparelli gown is exceptional (and had fans buzzing about potential easter eggs). It doesn’t hurt she has 300 carats of Lorraine Schwartz diamonds on.
Dolly Parton
Obviously you can’t see it in this photo, but Dolly is in head-to-toe pink here. These were the 1977 Grammys, and it wasn’t quite as common to see this colorful of a look at the ceremony. But Parton has played by her own rules, always, and this OTT bedazzled getup was no exception.
Prince
Prince in polka dots?? This 1988 photo doesn’t quite do it justice: The late icon is wearing one white glove and one black glove, and he’s wearing high heels—in matching polka dots, of course. The best part might have been the sharp, defined, enormous shoulder pads.
Mary J Blige
The world realized Mary J. Blige was a style icon, thanks to this outfit. Who knew head-to-toe leopard print could be so…glamorous? (The fact that it’s a one piece with hood helps it feel more rock and roll.) The gloves and matching sunglasses take it over the top, as does the fact that she matches her Grammy.
Mariah Carey
Mariah Carey, in the ’90s, with her stunning layered curly hair, and a simple black mini? Bingo!! According to her recollection in a Vogue interview, she thinks that Pamela Dennis designed it. “I know that I was very wrong for the earring choice. But whatever; I’m not going to disrespect the moment!” she remembered.
Miley Cyrus
For her history-making Grammys, in which she won her first trophy, Miley Cyrus wore a Maison Margiela gown made out of 14,000(!) gold safety pins that took 675(!!) hours to make, apparently. Also, this is how you do an illusion dress—she looks simultaneously covered and skin-baring.
Cher
Not long after filing for divorce from Sonny Bono, and debuting a new relationship at this very event (with David Geffen), Cher wore the brightest, prettiest, naval-baring butterfly outfit of all time. Coincidence? Likely not—Cher was known for her revenge dressing.
Britney Spears
This is one of my favorite Britney Spears outfits of all time; The singer was in the process of becoming a superstar, and she traded her cool schoolgirl costumes for a regal but simple Randolph Duke dress and Oscar de la Renta stole. She probably inspired every single prom dress that year.
Katy Perry
A dress with music notes on it?? In the wrong hands this might inspire eye-rolls, but on Katy Perry it’s camp perfection. It’s custom Valentino; and Perry told Ryan Seacrest, “It’s musical, for music’s biggest night.” She could wear this every year and I’d still love it every time.
Olivia Rodrigo
For her first Grammy nomination, Olivia Rodrigo went full ’90s vintage in a Vivienne Westwood Couture gown with pink crystal accents. It was a strong showing for the relative newcomer, who later upped the ante in a vintage Versace that was older than her. Ack.
Beyoncé
Beyoncé matched her awards to her gorgeous u-neck red gown (it’s custom Peter Dundas, who called her his muse)—and in an extra degree of difficulty, she’s pregnant with twins in this photo and still giving us maximum glamour. This made it to the top of our favorite Queen Bey red carpet looks.
Lady Gaga
If you’re headed to the Grammys for the first time, your instinct might be to choose a subtle outfit. But that’s not Lady Gaga’s style! She wore this gorgeous Armani Privé gown that looked to be inspired by the cosmos, even carrying her own metallic star and matching mega-heels.
Lizzo
If you love flowers, why not go to the Grammys as a literal bouquet? Lizzo wowed all of us in this cherry Dolce & Gabbana outfit, and she had a rosette in her hair and on her nails for good measure. If you missed it, this was also the event where Lizzo showed off boyfriend Myke Wright for the first time.
Cardi B
This architectural cobalt gown on Cardi B looks like a literal work of art. It’s from Gaurav Gupta’s spring 2023 couture collection, and she’s wearing the heck out of it. She also took the time to pose thoughtfully, including extending her hands into the air, which is why she’s a couturier’s dream.
Ariana Grande
Ariana Grande already looked amazing in this custom gray Giambattista Valli dress—the star is petite, and the gown apparently measured 20 feet in diameter. But when she just fully sat down, looking like a very strangely colored cupcake, we all stood up and applauded.
Jennifer Lopez
It’s very difficult to top Jennifer Lopez in the green Versace dress that everyone was talking about at the time and to this day (it was naval-baring way before that was a thing at the Grammys). J. Lo later noted that she was having a tough time finding a dress for the event, and the second she put it on, she knew it was the one.