27 Iconic Grammy Awards Looks

The Grammy Awards is one of the nights in which artists from all over America come forth and celebrate the talent of musicians. While the Awards are put together to recognize the efforts of our beloved artists, many of them use it to shock audiences with their bizarre outfit choices too! 

The red-carpet fashion brought by Grammys is something we’re all excited about. Artists pick out bold and unique outfits for this night, dressing up to create memorable and iconic looks for the pop culture and its devotees. From Lady Gaga to Jennifer Lopez, let’s discuss all these artists and see their bizarre outfit choices for the Grammys!

27 Iconic Grammy Awards Looks
Image Source: Grammy 

Aretha Franklin

Going back to 1972, Aretha Franklin wore an orange head-to-toe outfit and looked as splendid as ever. This was Aretha’s seventh and eighth Grammy awards, and she received these awards in style. 

27 Iconic Grammy Awards Looks
Image Source: Harpersbazaar

According to Harper Bazaar, the red and golden gown styled by Aretha Franklin was simply stunning and unique. 

Cher

At the Grammy Awards ceremony of 1974, Cher decided to be an actual fairy princess.

27 Iconic Grammy Awards Looks
Image Source: Huffingtonpost

Styling a butterfly clip on her hair and a gorgeously intricate detailing on her top, Cher made her entrance in the 16th Grammy Awards to present the Album of the Year for Innervisions with Stevie Wonders.

Dolly Parton

Much of the cowboy trend has been rejuvenated thanks to Lil Nas X and the yodeling boy from Walmart. However, in 1977 when Dolly Parton entered the Grammys dressed like a cowgirl from head to toe, it became an iconic look.

27 Iconic Grammy Awards Looks
Image Source: Dazeddigital

The singer was nominated for the Best Country Vocal Performance, but unfortunately, she lost the award to Emmylou Harris.  

Grace Jones

The singer has had several legendary looks that she has rocked throughout the award show, but her iconic outfit from 1983 wins the lottery for us. 

27 Iconic Grammy Awards Looks
Image Source: Getty Image

Grace Jones, the infamous multi-hyphenate, wore a leather and straw ensemble in the 1983 Grammys. She complimented the look with a bold hat while carrying beautiful gold-toned makeup.  

Michael Jackson

The legendary singer, Michael Jackson, has been no short of styling extremely fashionable looks throughout his career, but his look designed by Michael Bush from the 1984 Grammys wins them all. 

27 Iconic Grammy Awards Looks
Image Source: LIlianspace

Wearing a bedazzled military jacket, classic aviators, and white gloves, Michael Jackson won eight awards out of twelve nominations that night – breaking all the records through his fashion and musical successes. 

Prince

The king of all the flamboyant looks from his era, Prince styled the 1988 Grammy Awards while wearing a polka-dot suit and matching high-heel boots. 

27 Iconic Grammy Awards Looks
Image Source: Glamour

The legendary singer of ‘Purple Rain’ was nominated for three awards that night but couldn’t win any. However, his outfit was enough to make him memorable in the award show. 

Paula Abdul

Looking like a Grammy Award herself, Paula Abdul was about to win her very first Grammy for ‘Straight Up,’ and she didn’t come slow in terms of her apparel! 

27 Iconic Grammy Awards Looks
Image Source: Lilianspace

Her matching golden overalls from head-to-toe, starting from her scrunchie to jewelry and her shoes to the purse she held, made her look like the new star of the night. 

Selena

Channeling the glamour of Hollywood, Selena walked the ramp of 1994 Grammys while wearing a sparkly white gown to win her first Grammy award for the Best Mexican-American album.

27 Iconic Grammy Awards Looks
Image Source: Getty Image

 It ended up being the artist’s only win, but she was later honored by the Lifetime Achievement Award. 

Shania Twain

In the Grammys of 1994, Shania Twain pulled off a look that nobody thought one could look good in! 

27 Iconic Grammy Awards Looks
Image Source: Glamour

She wore a white long-sleeved turtleneck gown, covered in sparkles and designed by the infamous Marc Bouwer. The dress certainly did create a statement look for many more Grammys to come!

Mary J. Bilge

Nobody knows that it was Mary J. Bilge who first styled the leopard-print gown in the 1996 Grammys, with it still being in fashion today! 

27 Iconic Grammy Awards Looks
Image Source: Wwd

Mary was surely ahead of her time when she wore the gown, as in that era, only the leopard-print midi skirt had been in style. The R&B legend won the first Grammy of her career in this event for the song “I’ll Be There For You.” 

Jada Pinkett Smith

At the 1998 ceremony of the Grammy’s, Jada Pinkett made sure she was not hiding her baby bump! She styled her sparkly two-toned gown to the event when supporting her then-boyfriend Will Smith, who won the Grammy Award for the song from Men in Black. 

27 Iconic Grammy Awards Looks
Image Source: EW

At that time, she was expecting her first child, Jaden Smith.

Jennifer Lopez

In the Grammy Awards of 2000, Jennifer Lopez first stunned the crowd with her jungle-print Versace dress

27 Iconic Grammy Awards Looks
Image Source: People

J.Lo’s outfit choice ended up breaking the internet, and the dress became a very well-known designer outfit. In addition, the look was re-created as a closing-off to Versace’s Spring and Summer collection after getting inspiration from the artist.

Lil’ Kim 

In 2002, Lil’ Kim won the Best Pop Collaboration with Vocals Award in the Grammys, and her red carpet look for this award show was certainly something else.

27 Iconic Grammy Awards Looks
Image Source: Huffingtonpost

 The rapper decided to copy one of the most bad-ass looks in the Grammys, wearing red leather overalls with a bedazzled belt and a Chanel motorcycle helmet to compliment her look altogether.  

M.I.A

M.I.A was pregnant with her son in the Grammy Awards of 2009, but that didn’t stop her from making a signature statement through her outfits. The singer wore an outfit that described her spontaneous energy in the best ways possible! 

27 Iconic Grammy Awards Looks
Image Source: Eonline/ Pinterest

Her outfit was designed by Henry Holland, bringing out a black and white polka dot mesh ensemble that had her walking with pride while enhancing her pregnant belly. 

Lady Gaga

In the Grammy Awards of 2009, Lady Gaga arrived in her stunning intergalactic dress with statement heels to completely blow everyone’s minds off! 

27 Iconic Grammy Awards Looks
Image Source: lofficielusa

Not only that, but this outfit has just been the first out of the singer’s many bizarre looks throughout her career.

Lady Gaga 2.0

Again, in the Grammy Awards ceremony of 2010, Gaga made her entrance to the event as dramatic as possible. 

27 Iconic Grammy Awards Looks
Image Source: Lofficielusa

She entered the ceremony in a giant egg while four half-naked people carried her there. Later, the artist came up on the stage for her performance in the show “Born this Way.”

Rihanna

Wearing a see-through white striped gown, Rihanna’s dress from the Grammy Awards of 2011 was almost an optical illusion

27 Iconic Grammy Awards Looks
Image Source: Huffpost

The singer styled this look when she won her fourth Grammy, with her outfit being designed by Jean Paul Gaultier.

Fergie

The singer wore an orange see-through gown designed by Jean Paul Gaultier, which became extremely eye-catching for the audience. 

27 Iconic Grammy Awards Looks
Image Source: Popsugar

Fergie was nominated for two Grammys that night for her collaboration with Kanye West in “All of the Lights.”

Nicki Minaj

Using her song “Roman Holiday” as an inspiration, Nicki Minaj showed up to the Grammys wearing her crimson red Versace cape with the gown in the award ceremony of 2012. 

27 Iconic Grammy Awards Looks
Image Source: Getty Images

She also had a man accompany her, who was dressed as the Pope, to keep up with the dramatic entrance and go all in for the look! 

Beyonce

Styling a sheer white lace gown, Beyonce made her entrance to the Grammy Awards of 2014 in fashion. 

27 Iconic Grammy Awards Looks
Image Source: Redcarpet-fashionawards

The dress looked gorgeous on her, and while it was see-through, the singer was completely confident to flaunt her figure!

Rihanna

The singer left everybody speechless with her pink puffed-up dress at the 2015 Grammy Awards. 

27 Iconic Grammy Awards Looks
Image Source: Conversationsabouther

She was the last person to arrive at the event, but her outfit, designed by Giambattista Valli, surely got all the attention Rihanna asked for! 

Madonna

In the Grammy Awards of 2015, Madonna styled a look that people are still unable to forget! The singer wore a custom-designed Givenchy outfit which included a lace corset along with high-heeled boots. 

27 Iconic Grammy Awards Looks
Image Source: lofficielusa

The outfit complimented her figure greatly, and she stunned the audience even more by flashing her backside to them!

CeeLo Green

Unveiling the alter ego, Gnarly Davidson, CeeLo Green walked the red carpet in the award ceremony of 2017 while wearing a golden head-to-toe overall

27 Iconic Grammy Awards Looks
Image Source: lofficielusa

He followed the glamourous and unique dressing trends in the Grammy’s!

Cardi B

The rapper wore a gown that made her look like a gorgeous mermaid, which came straight out of the archives of Theirry Mugler. 

27 Iconic Grammy Awards Looks
Image Source: Glamour

The gown was featured in the Houte and Couture Mugler’s show of Fall and Winter of 1995, and her look certainly came out as memorable.

SZA

Creating a soft yet sexy look out of her gown, SZA wore the dreamy outfit designed by Atelier Versace. 

27 Iconic Grammy Awards Looks
Image Source: Mefeater

It had intricate ornate beadings and tulle on the dress, and the artist was nominated for five Grammys that night! 

Billy Porter 

Styling a sparkly look from head to toe, Billy Porter wore the bedazzling blue outfit in the award ceremony of 2020 with a mechanical hat with a fringe that would unveil his face. 

27 Iconic Grammy Awards Looks
Image Source: Glamour

He used blue eyeshadow on his eyes and colored his nails and lips silver to keep up with the look.  

Lil Nas X

Looking like a cowboy wearing pink, Lil Nas X walked the red carpet of the 2020 Grammy’s with the Versace-designed outfit. 

27 Iconic Grammy Awards Looks
Image Source: Glamour

He had a leather jacket on along with a mesh tank and a belted harness too. The rapper’s outfit was complemented by the signature gold motifs by Versace.

Conclusion

In short, fans will never be disappointed with the many signature looks created by talented singers throughout the era of Grammys, and as fashion becomes more and more creative, there are bound to be more!