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The 37 Most Iconic and Daring Grammy Looks in History

When it comes to red carpet events, there’s nothing quite like the Grammy Awards. Every year, the music industry’s biggest stars, with the occasional actor or two in the mix, gather to honor the songs and performers that filled the radio waves with sonic bliss. While it’s great to see our favorite divas perform on stage and receive their well-deserved accolades, the best part of the night is, hands down, the red carpet.

At the Grammys, stuffy notions of formal wear are cast aside in favor of fearless fashions that turn heads and push boundaries. Early on in the ceremony’s history, heavy hitters like Aretha Franklin, Dolly Parton, Grace Jones, and Whitney Houston set the bar high with bold and unique outfits. This evolution transformed the Grammy’s red carpet into a must-see event for fashion and music enthusiasts alike, with no shortage of iconic moments that have made their way into the history books of style.

For instance, just take Jennifer Lopez’s ab-baring Versace dress that literally helped create Google’s Image Search function, or Lady Gaga’s out-of-this-world Giorgio Armani galaxy dress. And who could forget the barely-there Maison Margiela dress made of over 14,000 gold safety pins that Miley Cyrus wore last year? With the 2025 ceremony just around the corner, let’s take a look back at some of the most memorable Grammy Awards looks of all time.

### Miley Cyrus, 2024
At last year’s red carpet, Miley Cyrus wore a literal labor of love. The singer donned a Maison Margiela modern flapper look that left little to the imagination. It was made from an elaborate arrangement of over 14,000 gold safety pins and took over 675 man-hours to create, showcasing her commitment to pushing fashion boundaries.

### Adele, 2023
After a six-year hiatus from the Grammys, Adele returned in full form at the 2023 red carpet, donning a crimson velvet Louis Vuitton dress. Her custom look featured an off-the-shoulder design with ruffled shoulder detailing, long sleeves, and a belted waistline. Tiffany & Co. jewelry added a twinkling shine, making her one of the standout stars of the evening.

### Dua Lipa, 2022
Dua Lipa struck a pose in a bondage-inspired Versace dress with sheer paneling at the bodice, giving the pop star an edgy flair. Glistening gold Medusa medallions and buckle hardware added brilliant bling to the black column dress, perfectly complementing her bold persona.

### Doja Cat, 2021
Leave it to Doja Cat to raise the style stakes. In 2021, she sauntered down the red carpet in a moto-inspired Roberto Cavalli gown, featuring a long-sleeved leather top zipped down to her bellybutton, paired with a skirt made of black and neon green plumes. Her daring look was a testament to her unique sense of style.

### Ariana Grande, 2020
Ariana Grande made a huge style statement in 2020 with a cloud-like, strapless Giambattista Valli creation made from countless yards of smoky grey tulle. She completed her look with satin opera gloves and her signature high ponytail, embodying a modern-day princess.

### Cardi B, 2019
This rapper dug through the archives of Thierry Mugler to pick out her 2019 Grammys look, choosing the famous “Venus” dress from the designer’s 1995/1996 couture collection. Its extravagant pearlescent bodysuit and shell-like satin skirt gave Cardi B the appearance of a surrealist sea creature, making her one of the most talked-about stars of the night.

### SZA, 2018
SZA looked like a dream as she sashayed down the red carpet in an angelic white tulle dress. The Versace design featured a beaded bodice, whimsical tulle sleeves, and a skirt with a thigh-high slit, perfectly capturing her ethereal essence.

### Celine Dion, 2017
Celine Dion has consistently wowed on the red carpet, but her daring emerald green Zuhair Murad dress in 2017 was particularly striking. The gown showcased not only her killer voice but also her impeccable sense of style, proving that she can do it all.

### Taylor Swift, 2016
Country-pop singer Taylor Swift turned heads in 2016 when she debuted a new edgy look and bob haircut on the red carpet. She wowed onlookers in a coral-colored bandeau top and a neon fuchsia pair of hotpants worn underneath a voluminous ball skirt courtesy of Versace.

### Rihanna, 2015
The “Diamonds” singer shined on the red carpet in an over-the-top pink frothy frock courtesy of couturier Giambattista Valli. Her strapless, empire waist bodice was covered with a braided sequin design that served as an anchoring balance to the tons of tulle that comprised her ball skirt.

### Madonna, 2014
This boundary-pushing artist subverted expectations in 2014, walking the red carpet in a black double-breasted Ralph Lauren tuxedo jacket with wide-leg trousers. She completed her tailored look with a wide-brimmed hat, crystal fingerless gloves, and a gentlemanly walking cane, showcasing her versatility.

### Alicia Keys, 2013
Alicia Keys exuded Parisian chic at the 2013 Grammy Awards in a slinky, black Azzedine Alaïa dress, which had a criss-cross croc-embossed leather bodice and a fitted fishtail hemmed skirt. She accessorized with serpent earrings and a flashy cocktail ring, embodying elegance.

### Nicki Minaj, 2012
Rapper Nicki Minaj polarized the internet with this scarlet silk satin red dress designed by Versace. Her bold look featured a huge hood with black embellishments on the edges; the treatment was also applied on the skirt to create an outline of the brand’s signature head of Medusa.

### Nicole Kidman, 2011
Oscar winner Nicole Kidman supported her country-singer hubby, Keith Urban, on the red carpet in a strapless, ruched floral printed Jean Paul Gaultier mermaid gown. Raw-edged petal ruffles covered the look’s neckline and skirt, giving the romantic look sweet movement.

### Lady Gaga, 2010
Mother Monster arrived on the red carpet in a simply out-of-this-world couture creation from design wizard Giorgio Armani. The pale purple high-low hemmed gown comprised sheer organza laid over an intricate tornado of boning, which she wore over a Swarovski-encrusted catsuit.

### Katy Perry, 2009
Lebanese fashion designer Basil Soda created this complex bubblegum confection for singer Katy Perry in 2009. The look featured a basketweave draped treatment throughout and an origami-like flourish at the hip, making her one of the most memorable stars of the night.

### Fergie, 2008
The “My Humps” singer elegantly showed off her curves in a strapless canary yellow Calvin Klein dress. Her minimalist look was given a visual punch with a panel of fabric in the back, creating a captivating cape-like effect.

### Jennifer Hudson, 2007
Hot off the press tour for her role in the musical Dreamgirls, actress and singer Jennifer Hudson showcased her fashion prowess in a blazing red dress that featured a gold snake adornment at the bust. She accessorized with gold bangles and matching strappy sandals.

### Christina Aguilera, 2006
Christina Aguilera ditched her “Dirty” phase and went for a silver-screen siren moment in 2006, wearing a pearl white bias-cut satin Roberto Cavalli dress paired with old-school Hollywood-inspired hair and makeup.

### Sheryl Crow, 2005
The “The First Cut Is the Deepest” singer appeared on the Grammys red carpet in a canary yellow halter dress. A heavily embellished deep cut-out at the waist and thigh-high slit steamed up Sheryl Crow’s style.

### Beyoncé Knowles, 2004
For her first solo Grammys, Beyoncé looked like a gold statue herself in a gold satin sweetheart dress designed by her mother, Tina Knowles, featuring a jeweled collar and delicate ruching at the bust and hips.

### Gwen Stefani, 2003
Gwen Stefani joined her No Doubt bandmates on the red carpet in an asymmetrical black and white polka dot dress from Vivienne Westwood. A heavy chain necklace, red pumps, and feathered boa completed the old Hollywood-style look.

### Britney Spears, 2002
The pop star channeled Julia Roberts in “Pretty Woman” in 2002, wearing a red dress with a low-cut cowl neck. A crown full of teased curls added drama to the fiery look.

### Destiny’s Child, 2001
This famous singing trio was often outfitted in custom looks designed by Beyoncé’s mother, Tina Knowles. Her designs typically combined showgirl-worthy extravagance with hip-hop influences, as seen in these looks the singers wore in 2001.

### Jennifer Lopez, 2000
You can thank this iconic Versace dress that Jennifer Lopez wore at the turn of the century for the creation of Google’s Image Search. The green palm-printed frock earned its place in the style history books due to its provocative sheerness and belly button-baring neckline.

### Shania Twain, 1999
Taking a break from her regular country chic aesthetic, singer Shania Twain went for sleek and modern in a long-sleeved turtleneck style column dress covered in shining sequins.

### Lauryn Hill, 1997
Fugees singer Lauryn Hill looked radiant in a sleek, red-and-white color-blocked column dress that had a plunging v-neckline. She accessorized with gold bangles and chalk white toe-strap sandals.

### Mary J. Blige, 1996
Singer-songwriter Mary J. Blige made a bold impression on the Grammys’ red carpet back in ’96 when she wore a leopard print top with matching pants and headscarf, complemented by black leather gloves and oversized sunglasses.

### Selena Quintanilla-Pérez, 1994
Although she was known to sew many of her own concert outfits, for the 1994 Grammys, Selena Quintanilla-Pérez famously bought her heavily embellished white Lillie Rubin dress from The Galleria Mall in Houston, Texas. A scene in her J.LO starring biopic would later pay a dramatized homage to the purchase.

### Mariah Carey, 1993
Sultry ’90s minimalism was the vibe for Mariah Carey’s 1993 Grammys look. She wore a form-fitting scarlet red ankle-length dress with crisscrossing spaghetti straps, accessorized with a matching tassel handbag and heels.

### Whitney Houston, 1986
Whitney Houston won her first Grammy in 1986 and showed up to claim her prize wearing a draped turquoise goddess gown. An asymmetrical crystal detailing at the shoulder added a bit of edge to her ethereal dress.

### Cyndi Lauper, 1984
The “Girl Just Wanna Have Fun” singer whipped up the fashion equivalent of a fruit cocktail in 1984, wearing a tropical floral print dress underneath a navy silk taffeta coat and piles of jewelry and tulle.

### Grace Jones, 1983
Provocative pioneer Grace Jones showed up in warrior attire to the Grammys’ 25th anniversary wearing a wide-brimmed bamboo kasa hat and a matching black leather ensemble with sharply shaped shoulders.

### Pat Benatar, 1982
Rockstar Pat Benatar went for pretty tough attire, wearing a frilly black mini-dress covered in shiny sequins, crisscrossing straps, and a contrasting waistband. She wore it over leggings for a more modest effect.

### Cher, 1974
Never one to shy away from a bold look, style chameleon Cher showed up in a bedazzled sequined butterfly bikini top with a matching headpiece. A white sheer shawl gave the barely-there look flowy movement.

### Dolly Parton, 1977
This country crooner’s flamboyant crystal-encrusted white and pink jumpsuit in 1977 combined a little bit of country, a little bit of rock-n-roll, and a whole lot of personality for a quintessentially “Dolly” look.

### Aretha Franklin, 1970
The “Queen of Soul” made a regal statement at the 1970 ceremony wearing a persimmon orange long-sleeved gown that was embroidered with golden thread, showcasing her status as a music icon.

The Grammy Awards red carpet continues to be a showcase of creativity, individuality, and bold fashion choices, making it a highlight of the entertainment calendar. Each year, we eagerly await to see what our favorite stars will wear, knowing that the night will be filled with unforgettable moments and stunning looks that will be talked about for years to come.

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