30 Of The Most Iconic Grammy Fashion Moments Of All Time

The Grammy Awards have always provided an antidote to basic gowns and safe tuxedos during awards season. We pick our most favourite looks ever.


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CHER, 1974

Wearing a large butterfly adornment on her head, Cher personified the glamour of the 70s in this midriff baring look.

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YOKO ONO & JOHN LENNON, 1975

Feather boas and berets added a bohemian vibe to this young couple's night out to the 17th Annual Grammy Awards.

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DAVID BOWIE, 1975

The Thin White Duke cuts a dashing figure in a wide lapel tuxedo, finished with blazing red hair from filming The Man Who Fell To Earth.

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DOLLY PARTON, 1977

The country legend goes full Texan barbie in a pink rhinestone look.

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GRACE JONES, 1983

Wearing a Samurai inspired outfit designed by Giorgio Armani, Grace was a pioneer for avant-garde fashion at the Grammy Awards.

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CYNDI LAUPER, 1985

Cyndi brought her own unique brand of New Romantics style in a tropical print skirt and full face of make-up.

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WHITNEY HOUSTON, 1986

Attending her first ever Grammy Awards to collect her first of many Grammy's, the Diva turned heads in this blue gown with sequin detail.

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SINEAD O'CONNOR, 1989

Performing her hit Nothing Compares 2U the Irish singer looked cool in a t-shirt, jeans an leather jacket ensemble that re-enforced her rebellious spirit.

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RACHEL HUNTER & ROD STEWART, 1991

Putting New Zealand on the map, our Rach and then husband Rod opted for block coloured blazers to the Arista Records pre-Grammy Party.

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EN VOGUE, 1991

Showcasing another example of why 90s fashion was fun, the RnB girl group follow in the tradition of same-same but different in these colourful outfits backstage.

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CELINE DION, 1992

A style icon then as she is now, the French-Canadian songstress opts for 90s cocktail chic in a black and embellished dress with matching shoes.

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1993 JANET & MICHAEL JACKSON

Both in angelic white, the sister and brother duo played with tailoring - Michael in a pearl embellished jacket and Janet in a sleek double breasted trouser suit.

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SELENA, 1994

Before she was murdered, the Tejano singer was on the brink of a successful crossover career, wearing a sequin gown to a Grammy Awards Show that announced her arrival into the English language market.

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TLC, 1996

T-Boz, Left-eye and Chili, along with Aaliyah, ushered in a tomboy style to female hip-hop fashion, that still resonates today. This all white and transparent set a definining look from their many great looks over the years.

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LENNY KRAVITZ, 1997

There are stylish men, then there is Lenny Kravitz. The rock star's singular style comes with plenty of authnetic attitude to pull off any look.

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LIL' KIM, 1998

Before Rihanna, there was Lil' Kim, the petit rapper (1.5m) is known for wearing outfits larger than life. This sparkly number is considered far more demure than some of her other award show looks, but showcases a trendsetter still experimenting with fashion.

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MADONNA, 1999

We've seen many incarnations of Madonna, and this ode to Memoirs of a Geisha proved to be one of her most dramatic, wearing a modern interpretation of a Kimono designed by friend Jean Paul Gaultier.

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ERYKAH BADU, 2000

Winning a Grammy that year alongside The Roots and Eve, Erykah keeps it chic in a mid length skirt, wrap blouse and her signature head wrap, looking every inch a modern day Jazz chanteuse.

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JENNIFER LOPEZ, 2000

A dress that arguably transformed Jenny from the block into J-Lo the bonafide superstar, this Versace gown announced the arrival of a Latin triple threat — singer, actress, dancer.

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BRITNEY SPEARS, 2000

Not to be outdone that same year, Britney shakes off her small town Louisiana wardrobe and tries out classic Hollywood glamour in this white gown and matching fur stole.

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AMY WINEHOUSE, 2008

Performing a live cross from London, the late singer knew how to make a dress her own, with her signature beehive hair do and winged liner, Amy's unique style was an antidote to cookie cutter gowns and Hollywood glamour so ofen seen at award shows.

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M.I.A, 2009

A very pregnant M.I.A opts for comfort in a Henry Holland outfit for her performance of Paper Planes.

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LADY GAGA, 2010

Wearing three different custom Armani outfis that night, this silver creation complete with intricate headpiece stole the show.

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ADELE, 2013

Valentino came on board to dress Adele on her special night where she won her Grammy for Best Pop Solo Performance. This classic nod to a 50s prom dress adds some class to the red-carpet festivities.

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PHARRELL, 2014

Getting snapped alongside a style icon like Steve Nicks would be daunting for most, but Pharrell steals the show in this Vivienne Westood hat and Adidas Originals tracksuit top.

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RIHANNA, 2015

Not one to miss out on a fashion moment, Rihanna's greatest Grammy look is a contentious choice, but we think this pink Gimabattista Valli couture gown takes the honours with its sense of whimsy and fun.

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BEYONCE, 2017

She's a Grammy veteran by this point, but her Mother Earth routine that year in a custom gold Peter Dundas look with an embellished halo adorned with gold roses was a stunning way to put her Lemonade era to rest before giving birth to twins and embarking on the next album.

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SOLANGE, 2017

Sister Solange also went for a Midas touch in this pleated Gucci number.

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SZA, 2018

Looking ethereal in an ornate Atelier Versace gown, the singer who was nominated for five awards last year.

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LANA DEL REY, 2018

Channeling legendary 1930s starlet Hedy Lamarr, Lana goes celestial with a Gucci gown and silver halo.

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