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From Madonna In Gaultier To Taylor In Gucci, The Best Grammy Awards Looks Of All Time

A different, more experimental, set of sartorial rules apply at the Grammy Awards, which makes for a sweet feast of fashion. Here, the best looks of all time.

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At the Grammy Awards, a freedom of fashion expression prevails. The music ceremony, which has been going since 1959, has long been something of a fashion playground where the worlds of music and style collide in riotous experimentation and campy joy executed in plenty of sequins and sparkle.

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Each year, stars that are nominated, performing or being honoured turn up in looks that are sometimes custom, perhaps couture but very often at the cutting-edge of each personality's style. If there's an awards show to make a fashion pivot, then it's the Grammy Awards where it tends to take place. Heck, Lady Gaga once arrived in an egg!

The Grammy Awards' most-memorable outfits have also made history. A plunging Versace gown worn by Jennifer Lopez in 2000 was cause enough for Google to launch Google Images and plenty of others have since followed suit to ensure that its their name and look in your search bar the morning after the night before.

Now, ahead of the 2025 ceremony taking place this weekend, we throwback to the best to ever do it thus far. Try to pick a favourite.

Here are ELLE UK's favourite Grammy Awards looks of all time:

Grace Jones at the 25th Grammy Awards, February 1983

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Jones chose a conceptual look by Issey Miyake for the early-Eighties affair.

Erykah Badu at the 42nd Annual Grammy Awards, February 2000

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The musician collected her third Grammy Award wearing a green wrap top worn with a striped skirt, standout red heels and a pale yellow head scarf at the first awards of the new millennium.

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Gwen Stefani and Courtney Love at the 40th Grammy Awards, February 1998

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The friends wore looks that were typically of the era at the 1998 celebration.

Adele at the 55th GRAMMY Awards, February 2013

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The British singer wore a floral A-line Valentino dress at the time when Maria Grazia Chiuri and Pierpaolo Piccioli were the house's co-creative directors.

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Taylor Swift at the 56th Grammy Awards, January 2014

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Swift has been a constant presence at the awards since first attending in 2008. For all the gowns and frocks she's worn, however, it's this sparkling Gucci number that shines brightest.

Rihanna at the 57th Grammy Awards, February 2015

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In Giambattista Valli, Rihanna proved that bigger is sometimes better.

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Mariah Carey at the 33rd Grammy Awards, February 1991

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An LBD never goes out of style, especially when worn with a handful of Grammy Awards.

Cardi B at the 61st Grammy Awards, February 2019

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A most memorable look of the modern era was Cardi B in a shell-like Mugler gown from its AW95 couture collection.

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Lady Gaga at the 61st Grammy Awards, February 2019

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Sure, there have been Lady Gaga Grammy red-carpet looks that have proven more standout, more avant garde than this Celine gown, but the stripped-back simplicity rendered in metallic is a winning option for us.

Aretha Franklin at the 13th Grammy Awards, March 1971

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The legendary musician wore diaphanous asymmetric gown to collect the award for Best R&B Vocal Performance. Before her death in 2018, Franklin won a total of 18 Grammy Awards.

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FKA Twigs at the 62nd Grammy Awards, January 2020

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The British musician wore a dramatic gown by Central Saint Martins graduate Ed Marler for the LA awards show.

Lizzo at the 62nd Grammy Awards, January 2020

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The American musician always makes the most of her red-carpet moment. This Atelier Versace rainwater gown is a highlight.

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Ariana Grande at the 62nd Grammy Awards, January 2020

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Before she became pink's most devoted spokesperson, pop music's most famous nephophile leant into her obsession in a gargantuan Giambattista Valli gown.

Megan Thee Stallion at the 63rd Grammy Awards, March 2021

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For a jolt of classic Hollywood glamour, the rapper turned to Dolce & Gabbana for this striking orange gown, reminiscent of Marilyn Monroe's Gentlemen Prefer Blondes dress.

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Dua Lipa at the 63rd Grammy Awards, March 2021

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Lipa dressed up in her dazzling Versace finery to walk the red carpet at the 2021 ceremony, where she won Best Pop Vocal Album for Future Nostalgia.

Mary J Blige at the 38th Grammy Awards, February 1996

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A legendary look for the ages, Blige wore a total leopard print Dolce & Gabbana ensemble for the 1996 affair.

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Billie Eilish at the 64th Grammy Awards, March 2022

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Eilish called on Rick Owens for her outré look for the Grammy Awards in March 2022. The all-black look set the singer in a new sartorial direction.

Lana Del Rey at the 66th Grammy Awards, February 2024

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The queen of sweet retro dressing chose a black vintage dress for the 2024 awards show, accessorising with a new fringe and sheer gloves.

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Boygenius at the 66th GRAMMY Awards, February 2024

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The trio coordinated in white suits by Thom Browne, illustrating a fresh approach to matching girlband dressing.

Laverne Cox at the 66th GRAMMY Awards, February 2024

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The actor chose an especially brilliant red Comme des Garçons dress, first seen in its SS15 collection.

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