By Jessica Wedemeyer
1:00pm PST, Feb 6, 2024
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We might not always remember who took home top honors at the Grammys, but we definitely remember the sexy, shocking and wild ensembles our favorite superstars donned on the red carpet. When it comes to Grammy style, anything goes! As we eagerly anticipate what the stars will wear to the 2024 Grammys on Feb. 4, Wonderwall.com is taking a look back at the most memorable looks of Grammys past… starting with this major red carpet moment…
Lady Gaga paid tribute to David Bowie with her 2016 Grammys ensemble — a deep blue embellished Marc Jacobs jacket dress with swirling cosmic designs. She completed the look with a red hairstyle à la Ziggy Stardust and ridiculously high platform heels.
Keep reading for more memorable Grammy looks…
MORE: Stars at their first Grammy Awards
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Like it or not, there's no denying that Jennifer Lopez's barely-there silk chiffon dress at the 2000 Grammys is one of the most recognizable red carpet looks in Hollywood history. The singer-actress flaunted her perfect figure, somehow managed to avoid a major wardrobe malfunction and cemented her place as an international superstar in the process.
MORE: Stars who've won the most Grammys
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The Pepto-Bismol pink Giambattista Valli ballgown that Rihanna wore to the 2015 Grammys took over her petite frame, but the pop star didn't care: "I saw this dress on the Internet and just fell in love with it," she explained of her famed "cupcake dress."
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Britney Spears arrived at her very first Grammys in 2000 looking regal — like a pop princess, some might say! The superstar, then new to the scene, donned this memorable all-white ensemble, which included a form-fitted gown with a matching fur stole.
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British rapper M.I.A. was three days away from giving birth to her first child when she attended the 2009 Grammys, so we can't blame her for choosing comfort over couture, but the two ensembles she donned before and during the show were just… WOW! On the red carpet, M.I.A. made the worst dressed list by keeping her sizable baby bump under wraps in a psychedelic Little Bo Peep-inspired dress with matching sneakers. Later, she changed into a sheer jumpsuit with strategically placed polka-dot embellishments. The ensemble certainly raised eyebrows, but it also became one of the most iconic looks in Grammys history — and we gotta love a woman who celebrates her pregnancy bod just a few days before delivering. In the end, we tip our hats to this memorable fashion risk.
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No Doubt frontwoman Gwen Stefani was pregnant with her first child, son Kingston Rossdale, when she attended the 2006 Grammys in this one-shouldered leopard-print ombre frock from her own L.A.M.B. line. Gwen scored bonus points for coordinating with the green carpet and brown backdrop at the Grammys that year.
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At the 2022 Grammys, Justin Bieber made a fool of himself in this comically baggy Balenciaga getup anchored by a hot pink beanie and massive clown-like shoes.
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Ariana Grande stunned at the 2020 Grammy Awards in this ethereal grey ballroom gown by Giambattista Valli. She didn't stop there — she also wore 30-carat diamond earrings by Lorraine Schwartz worth $2.5 million. We love the drama of this ensemble!
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Billie Eilish chose this bizarre black-and-green Gucci suit for the 2020 Grammys. From the sheer face mask (and this was pre-coronavirus pandemic!) to the fingerless gloves, this look was all in the details!
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Adele had that new-mom glow at the 2013 Grammys! She wore a short, vintage-inspired red Valentino dress — and looked like a total doll in the lacy creation.
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Lady Gaga shot for the moon and landed among the stars at the 2010 Grammys when she donned this custom-made Giorgio Armani Privé ensemble on the red carpet. The space-inspired getup was just one of three separate looks the fashion house designed for Gaga that night: They also created the sparkly green jumpsuit she wore to perform alongside Elton John during the telecast as well as an ice queen-inspired look featuring an intricate headpiece that she wore while accepting her multiple Grammys that year. It was arguably the height of Gaga's avant-garde fashion aesthetic, before her style veered into wacky performance-art territory.
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Toni Braxton shocked fans at the 2001 Grammys when she wore this scandalous gown. The white and silver frock, which was essentially a few pieces of fabric strategically placed together, also required that the star go sans undergarments. Pretty risky for the early 2000s!
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We love a colorblock moment! In 2016, Taylor Swift wore this vibrant coordinating set by Atelier Versace on music's biggest night. her styling was perfect with minimal jewelry, a chic bob and a matching bold lip.
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Well, Cardi B certainly made a splash at the 2019 Grammy Awards. The star arrived in this vintage Mugler design — one of her wildest looks ever. The piece — pulled from the fashion house's 1995 archives — was comprised of a sheer sequined bodysuit tucked into a black skirt that bloomed into a clam shell shape. Yep, that's right: a clam shell.
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Beyonce, who was pregnant with twins at the time, looked like a sun goddess while performing at the 2017 Grammy Awards. The superstar singer wore an ethereal gold gown by Peter Dundas complete with intricate golden beading, sheer details and a stunning gold headdress. Fun fact: In the middle of Bey's gown is a medallion fashioned to look like her face!
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Such a throwback! At the 2000 Grammy Awards, Christina Aguilera looked incredibly Y2K in her shimmery asymmetrical gown. The singer took home the award for best new artist that year.
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How cute is she?! At the 1977 Grammy Awards, Dolly Parton looked like a country sweetheart in her seriously bedazzled fuchsia jumpsuit.
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Katy Perry's dress did the singing for her at the 2014 Grammys. The sheer Valentino gown featured black music notes across the skirt. "It's musical, for music's biggest night," she told E!'s Ryan Seacrest of her sartorial inspiration.
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Serious question: Did this trio ever have a bad red carpet moment? At the 1996 Grammy Awards, TLC — Chilli (Rozonda Thomas), Left Eye (Lisa Lopes) and T-Boz (Tionne Watkins) — wore matching white outfits. Equal parts sexy and cool, these ladies looked oh-so '90s.
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Madonna channeled a bullfighter at the 2015 Grammys in a super-skimpy Givenchy creation with thigh-high boots and full-length gloves. And if you're wondering what was going on in the back, let's just say we shouldn't show you how revealing the look was from that angle.
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Kim Kardashian might have risked a major wardrobe malfunction in this shimmery, slinky Kaufman Franco gown at the 2011 Grammys, but boy did she look good doing it! "I'm like a bronze trophy right now," Kim told InStyle while flaunting her famous figure.
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Alicia Keys may have taken home five trophies at the 2002 Grammys, but when it came to her red carpet style, she was a total loser. We're not sure what's worse: the embellished jeans and plain white tank top, the sheer sari or the overly enthusiastic glittery eye shadow. Let's just say Alicia has come a long way since 2002!
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Carrie Underwood looked regal at the 2022 Grammys in this gorgeous golden Dolce & Gabbana ballgown fit for a queen. From the beautiful sash sleeve and embellished spaghetti strap that matched the rest of the bodice to the beautiful gathered full skirt, we adored every inch of this dreamy design.
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The men of Coldplay — Chris Martin, Will Champion, Guy Berryman and Jonny Buckland — attended the 2009 Grammys in multi-colored military jackets. Though the colors were mismatched, everything tied together with the musicians' shoes for a memorable red carpet moment.
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Yikes! Nicki Minaj drew major criticism when she walked the red carpet at the 2012 Grammys in an embellished red nun's habit, escorted by a man dressed as a pontiff. Was it sacrilegious — or just a major crime against the fashion gods?
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In 2003, Pink hit the Grammys in this messy gothic getup that featured sheer black paneling and haphazard cut-outs as well as a super-high slit. That messy faux-hawk hairstyle didn't help matters, ensuring that the final look was more sloppy than slick.
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There once was a time known as the early aughts, when girl groups and boy bands reigned supreme and coordinating in matchy-matchy ensembles was all the rage. At that time, no one did it better than Kelly Rowland, Beyonce Knowles and Michelle Williams of Destiny's Child. At the 2001 Grammys, the trio donned metallic gowns on the red carpet — we guess putting Beyonce in gold was too obvious! — and figure-flaunting green-and-gold ensembles later in the show. Each look was designed by Bey's mom, Tina Knowles. "She's the only person who knows what we want," Queen B told People magazine.
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Oh, CeeLo Green! He certainly made an entrance at the 2017 Grammy Awards decked out in this, well… we're not quite sure what to call it. The all-gold ensemble left us utterly confused, but was certainly hard to forget!
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Is that really Fergie? The Black Eyed Peas frontwoman looked simply glamorous at the 2008 Grammys in a canary yellow Calvin Klein number. It was a step in the right direction for the newly engaged singer — Josh Duhamel had proposed just two months earlier. Fergie proved that she was just as Fergalicious in mature, age-appropriate ensembles as she was dressing half her age in figure-flaunting fashions. Nicely done!
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The king and queen of country music were perfectly in sync in coordinating lilac at the 1999 Grammy Awards. Faith Hill took a fashion cue from Gwyneth Paltrow at the time, donning a totally au courant simple spaghetti-strap gown with a draped neckline, while Tim McGraw looked polished in his signature look: a well-fitted suit with a matching cowboy hat. The duo looked every inch country music royalty, doncha think?
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Jennifer Lopez had one of the worst looks of the night at the 2019 Grammy Awards. From the fit to the cut, we've never seen J.Lo in an ensemble so poorly tailored. Even the intricate jeweled embellishments couldn't save this bizarre sleeveless Ralph & Russo frock, which she topped off with a ridiculous hat to solidify the look as a miss.
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As far as weird Grammy fashion goes, alt-rock foursome OK Go take the cake! The "Here It Goes Again" rockers donned these wallpaper-inspired suits at the 2007 Grammys — and later recycled the looks for their "Do What You Want" music video. Were they trying to cut back on costs? Hey, it's tough being an indie act: Lady Gaga got three crazy outfits for the 2010 Grammys, and poor OK Go only got one set of acid-flashback-inducing suits for the entire year of 2007!
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At the 2006 Grammys, Kanye West arrived in this memorable ensemble: a red shirt almost completely unbuttoned to expose gold chains, a crisp white suit jacket and black pants. But it was his accessories that took this outfit to a bizarre new level. Check out those futuristic shades and black leather gloves!
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At the 1974 Grammy Awards, Cher sported a white crop-top with a sequined butterfly across the middle. She completed her look with a matching headpiece.
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A patterned skirt with palm trees? Check. A gold silk shirt? Check. A blue blazer, red tights and red pumps? Check, check and check. Cyndi Lauper brought every color of the rainbow to the 1984 Grammys. And she even added an odd tulle headband and beaded necklace to accessorize as only she can.
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We've seen few dresses as extravagant as this! At the 2020 Grammy Awards, Gwen Stefani opted for a seashell-adorned minidress by Dolce&Gabbana and completed her look with a pair of thigh-high boots.
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That's a whole lot of print! Brad Paisley rocked a white floral-print shirt under a jacket with lining featuring yet another floral print at the 2004 Grammys.
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On the one hand, Sheryl Crow's body looked unbelievable in this midriff-baring yellow gown at the 2005 Grammys. On the other hand, the singer — who wore yellow to support then-boyfriend Lance Armstrong's Livestrong Foundation — kind of looked like she was about to be constricted by a snake made of tinsel. And that is never good.
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Lil Kim's outfit at the 2002 Grammys certainly turned heads. The rapper sported a white collared crop-top under a cropped red leather jacket with matching boots and pants, plus a blinged out belt, oversized red shades and a Chanel motorcycle helmet that she carried on the red carpet. Because, why not?
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We absolutely loved Rihanna's Armani Privé look at the 2017 Grammys! The Bajan singer paired an orange crop top with a full black skirt and completed her look with a black clutch and diamonds.
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"Goofy" is certainly one way to describe Macy Gray's 2001 Grammys getup. The singer rocked baggy bedazzled jeans with pink boots, a hot pink T-shirt emblazoned with "Goofy" and a massive floor-length white fur coat. She completed her look with rose-colored glasses and streaks of pink in her hair.
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Mary J. Blige made heads turn at the 1996 Grammy Awards in this head-to-toe leopard-print ensemble. She completed the bold look with a pair of black sunglasses and matching leather gloves. Iconic!
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Then-newcomer Avril Lavigne shirked tradition by wearing an ensemble of her own design — or was it from Hot Topic? — rather than a designer gown at the 2003 Grammys. She probably hoped her oversized jacket, bow tie, worn-down sneakers and skull-and-crossbones belt buckle would convince us of something that her music just cannot: that she's totally punk rock. To us, the whole thing came off as really immature and kind of petulant. What do you think?
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Rihanna can basically wear anything and look flawless, which she proved at the 2011 Grammys when she stunned in a sheer white Jean Paul Gaultier gown featuring horizontal rows of tulle ruffles.
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Rapper Cardi B made quite a statement at the 2018 Grammys in this angelic yet avant-garde Ashi lace dress with butterfly sleeves and a train.
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SZA also delivered an angelic style moment at the 2018 Grammys in a sheer sequined Atelier Versace gown with tulle sleeves, an intricate sheer beaded bodice and thigh-high slits.
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Styling her hair in curls tucked behind a headband, Faith Hill's beauty look at the 1999 Grammys was very of-the-era. But this funky printed tank dress? There's no excuse for this flashy, loud look that we wish we could forget.
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Halsey served up a pretty memorable moment at the 2017 Grammys with this Christian Wijnants ensemble. She skipped wearing a shirt and instead showed up in just a royal blue jacket and parachute pants.
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If you've ever wondered what happens when an ostrich mates with a flapper, fear not: Christina Aguilera has the answer. The singer donned this overdone lilac confection at the 2004 Grammys. Sadly, she also attempted an Old Hollywood glam hairdo, but with her nearly black hue, this getup just didn't hit the right notes.
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Will Smith went all out at the 1999 Grammy Awards in an olive leather jacket with dark lapels that matched his leather pants. Guess he was gettin' jiggy wit it!
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The wig? The dress? We can't decide which of Cher's fashion faux pas was worse at the 2008 Grammys, during which she donned this bizarre, over-the-top gown featuring a massive train.
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Nicki Minaj looked wildly outrageous at the 2011 Grammys in a head-to-toe leopard-print Givenchy outfit with matching boots and a gravity-defying wig.
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Mya gave us classic '90s style at the 1999 Grammy Awards in a blue suit and matching bralette featuring embroidered flowers.
