The 37 Best and Boldest Grammy Looks of All Time

Cher walked so Miley Cyrus could run.

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. And while it's great to see our favorite divas perform on stage and get their well-deserved flowers, the best part of the night is, hands down, the red carpet.

You see, at the Grammys, stuffy notions of formal wear are cast aside in lieu 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 in terms of bold and unique outfits. From there, the Grammy's red carpet has seen an evolution that transformed it into a must-see for fashion and music stans 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 at last year.

With the 2025 ceremony this weekend, look back at the 37 best 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 wore 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.

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 with ruffled shoulder detailing, long sleeves, and a belted waistline. Tiffany & Co. jewelry added twinkling shine.

Dua Lipa, 2022

Dua Lipa struck a pose in a bondage-inspired Versace dress with sheer paneling at the bodice, which gave the pop star an edgy flare. Glistening gold Medusa medallions and buckle hardware added brilliant bling to the black column dress.

Doja Cat, 2021

Leave it to Doja Cat to raise the style stakes. In 2021 she sauntered down on the red carpet in a moto-inspired Roberto Cavalli gown which had a long-sleeved leather top zipped down to her bellybutton paired with a skirt made of black and neon green plumes.

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.

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.

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.

Celine Dion, 2017

Celine Dion has showed up and showed out on the red carpet in jaw-dropping fashion time after time, but especially in this daring emerald green Zuhair Murad dress, that showed that she doesn't just have a killer voice but a killer sense of style to boot.

Taylor Swift, 2016

Country-pop singer Taylor Swift wowed onlookers when she debuted a new edgy look and bob haircut on the red carpet in 2016. She turned heads 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.

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.

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 looks' 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 of 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.

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 showed off her fashion prowess in this 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 asymeterical 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, ed-and-white color-blocked column dress that had a plunging v-neckline. She accessorized with way 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 with 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.