Memorable And Bold Grammy Outfits From 1977-2023

The Grammys is an award show we look forward to every year to celebrate the incredible music made throughout the year. But, we also look forward to seeing the red-carpet looks that celebrities step out in.

In 2015, Sia and her sidekick Maddie Ziegler showed up to the red carpet of the Grammys in matching wigs that just could not be missed. Maddie is a dancer that had already appeared in more than one of Sia’s music videos so it was no surprise that they showed up together.

One of our favorite Grammy looks came from Cyndi Lauper back in 1984. Artists like Lady Gaga and Cardi B are well known now for their bold fashion statements but before them came Cyndi in this tropical look.

CeeLo Green showed up to the 2017 Grammys with a look that no one could have expected. Typically, we see the ladies being more adventurous with their style on the red carpet but CeeLo decided to shock us all with this gold look. 

Cher has had more iconic looks than we could count on our two hands, but her 1974 Grammys red carpet outfit sure left a lasting impact on fashion. In fact, Kim Kardashian herself has recreated this look which left its mark on fashion history.

Dolly Parton is never one to shy away from the color pink or big hair. She’s known for her country fashion and sequined looks. The 1977 Grammys were no different.

Michael Jackson wore more than one truly iconic look to the Grammys over the years as well as other awards shows and on stage. But this outfit from 1984 was especially noteworthy as it inspired what would later become his iconic look.

At the 25th Grammys anniversary in 1983, Grace Jones stunned everybody with her avant-garde fashion. The singer pretty much shut down the entire red carpet in style!

Prince was well-known for pushing against gender norms in fashion. Leave it to the icon to make what could have been a plain outfit, fashionable and appealing. His 1988 Grammys look certainly verified the fact that he was always dressed to impress.

Paula Abdul served up a true late 1980s, early 1990s look in this photo taken at the 1990 Grammys. The outfit channels ‘80s prom meets New Year’s Eve glitz and glamor and she nailed it completely. 

That same night, Selena won in the Best Mexican/Mexican-American album category for her Selena Live album. It went down as one of the most notable and celebrated moments in the music career of the American Tejano queen.

The year 1996 was full of many trends: Adidas track pants, backpack purses, and the preppy look. On the same note, the 1996 Grammys saw lots of creative and wild looks. But, that night, the legendary girl group, TLC, made fashion history. 

In 2000, Britney Spears’ classy outfit at the Grammy Awards was inspired by none other than Marilyn Monroe. Spears looked simply exquisite in the all-white Randolph Duke halter gown and Oscar de la Renta stole. Her sleek, straight hair definitely made her entire look an unforgettable Y2K moment. 

At the 2005 Grammy Awards, abs were what everybody was talking about. Sheryl Crow rocked a toned physique while wearing a gorgeous cutout yellow Robert Cavalli gown that’s slightly form-fitting. The dress’s halter neckline and 3D gold embellishments lent an airy balance with the rest of the gown. Truly, it was a bold and unexpected outfit. 

Nominated as one of the collaborators on “All of the Lights,” which would take home two Grammys in 2012, Fergie stunned everyone in a Jean-Paul Gaultier orange lace dress. It had ruffle sleeves and a small train. 

Whether you stay up to date with Kylie Jenner and her famous family or not, there’s no denying that the star and beauty guru’s baby pink Balmain jumpsuit was a highlight of the 2019 Grammys. That year, pink was a popular theme at the awards show and Jenner definitely fit the bill. 

The American R&B singer-songwriter, H.E.R., rocked a radiant and flowing yellow jumpsuit at the 2022 Grammys. The jumpsuit was embellished with phoenix embroidery and floor-length sleeves, complete with orange-tinted sunglasses. It looked like she stepped right out of the ‘70s! 

Lil Nas X is known for pulling stunts before he even hits the red carpet. Before showing up at the 2022 Grammys, he tweeted that he had already “arrived.” Nevertheless, it’s only fitting that his outfit would also be somewhat of a spectacle. 

For her second Grammys appearance, pop sensation Olivia Rodrigo must have turned heads on the red carpet at the 2023 awards show. Donning a sheer black slip maxidress with spaghetti straps from Miu Miu, the look is elegant and simple. Rodrigo accessorized by wearing a black pendant necklace, bean silver stud earrings, and a few matching rings. 

At the 2023 Grammys, Adele stuns in a red velvet Louis Vitton custom-made dress. She looked nothing short of flawless as she accepted her Best Pop Solo Performance Grammy for “Easy on Me.”

Jennifer Lopez arrived in sparkly style at the 2023 Grammys and was undoubtedly one of the fashion highlights of the evening. J-Lo’s gorgeous and plunging dark-blue Gucci dress was adorned with rhinestones. The ruffly dress with a thigh-high slit was complimented perfectly by sparkling Bulgari jewelry. 

The 2023 Grammys witnessed Kim Petras’ goth-bride-inspired, vintage Victor Costa look. It was completed with a red veil and matching gown. Petras appeared on the red carpet alongside her fellow “Unholy” singer Sam Smith, who donned a floor-length red gown with matching gloves. 

In 1996, Mary J. Blige won her very first Grammy which would set the stage for her career filled with awards and recognition. She wore this iconic leopard print outfit that would inform fashion for years.

This plunging dress quite literally broke the internet. When J-Lo showed up at the 2000s Grammy Awards, so many people were searching Google to see her in this iconic look that Google was actually inspired to create the Google Image Search so people could find exactly what they were looking for. 

You can’t talk about Grammy’s fashion without bringing up the icon herself: Lady Gaga. She has shown up in many wild and wacky looks but this futuristic alien-inspired outfit in 2010 is certainly one of the most notable. 

We are constantly amazed and at times disturbed by the fashion choices of the elite. Perhaps we just simply don’t have the eye for fashion that others have. One of the most confusing statements that Lady Gaga ever made was showing up to the 2011 Grammys in an egg. 

Harry Styles won best album at the 2023 Grammys and showed up in an outfit oh so fitting of the artist. Outside of being the heartthrob of his generation, Styles has become well-known for playing with his personal style in new and inventive ways.

Megan Fox and Machine Gun Kelly showed up to the 2023 Grammy awards in (somewhat) coordinated outfits. Megan adorned a stunning white dress with jeweled details and MGK had a unique silver suit.

The ever-talented singer and songwriter, Pharrell made a bold fashion statement at the 2014 Grammys which sparked internet chatter everywhere. 

Cardi B wore perhaps the most memorable look of the 2019 Grammys. People were very split on whether they liked or disliked the look but it was certainly the most talked about outfit of that awards season. 

Rihanna showed up making a statement in this huge pink dress to the 2015 Grammys, bringing new meaning to the phrase “go big or go home”. The singer and businesswoman looked stunning in this poofy pink dress but that didn’t stop the internet from creating tons of memes about it. 

2016 was a huge year for pop music and two icons of the year were Taylor Sqwift and Selena Gomez. The gal pals decided to be each other’s dates to the award ceremony and rocked memorable and colorful looks that will not soon be forgotten. 

Rockstars don’t wear shirts. At least, that was the philosophy of the Red Hot Chilli Peppers at the 1993 Grammys. These studs were riding a high after their Grammy wins (clearly).

In 1993 Celine Dion wore a dress that later became very popular at award shows and in fashion in general over the ensuing years. The dress might not look all that assuming from the front but as soon as she turned around…

Many of the looks that came to the Grammys in the 90s and early 2000s became very iconic but more recent looks have stirred up talk in the fashion community as well. One such look was Ariana Grande’s huge ballgown in 2020.

Lizzo was coined the “Fashion Queen” of the most recent Grammys for the multiple outstanding looks she rocked at the show. The artist broke out with multiple Grammy wins this year and even happened to match with Beyonce in one of her silver puffy-sleeved dresses.

We’re not sure if Shania Twain wanted to emulate Cruella De Ville or if it just happened by accident. Her hat is even bigger than Pharrell’s hat that sparked memes across the internet. 

The legendary singer arrived at the 2022 Grammys with a look that could not be ignored. People could not stop talking about the chain shirt that he paired with tight leather pants. 

Pilly Porter is known for his daring fashion looks and always manages to stun us with his ingenuity. Even so, this blue sparkly look stunned everyone in 2020. 

You can’t really talk about fashion in the music industry without talking about the iconic Madonna. She set the stage for lots of different kinds of styles throughout the years and inspired many artists to this day. 

Nicki Minaj showed up to the 2012 Grammys in one of the most surprising ensembles we’ve ever seen on the red carpet. She was dressed by Versace and brought a very interesting accessory.

In 2020, Billie Eilish wore an outfit that only she could rock. The young artist has quickly made a name for herself in music and in fashion with her completely unique voice and style.

Doja Cat has gained popularity for her unique and ever-changing style. Most recently, she is well-known for shaving her head and eyebrows. But in 2021, she stepped out at the Grammys with this completely unique costume.

Harry Styles has worn lots of boundary-pushing outfits that have sparked conversation on the internet over the years. His 2021 Grammy look was one such occasion.

Katy Perry arrived in this dress on the 2019 Grammy red carpet and certainly stood out. The pop star has become pretty well known for her colorful and daring looks over the years. 

Beyonce has attended the Grammys many times over the years and has worn beautiful looks that deserve tons of recognition. This was her most recent look in which she broke an unbelievable record.