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28 of Madonna's best looks

Madonna is the undisputed Queen of Pop - but she's also fashion royalty, setting trends and breaking rules.

Madonna. A woman so famous she doesn't need a surname.

The world's best-selling female artist of all time, she's not just a part of the culture, she's helped shape it since the 1980s.

It was because of artists like Madonna that the lines blurred between musician and muse, pop star and artist. From her debut - with bushy eyebrows and multiple bracelets - Madonna has done more than follow trends, she's set them. And then she's broken them and rewritten the rules for a whole new generation, over and over again.

There's never going to be another quite like the Material Girl, so let's enjoy a look back at some of her most era-defining looks over the years...

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Meet Madonna - the debut of an icon

Madonna was iconic from the get-go. bursting into the mainstream with a look that was copied by legions of fans across the world. Madonna's debut appearance included heavy eyebrows, colourful makeup, messy hair, big bows, beads, lacy gloves - and lots and lots of bracelets and rosaries.

This look was emulated by her fans, who were dubbed Madonna Wannabes in the press.

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Papa Don't Preach, 1986

In 1986, Madonna released the music video for Papa Don't Preach, a track from her True Blue album. The song was another controversial moment for Madonna - with the lyrics criticised by some for supposedly encouraging teenage pregnancies, but praised by others for embracing a tricky topic - and the video cemented one of her most recognisable looks.

Debuting a wet look, punky hairstyle, Madonna's Italians Do It Better t-shirt became a symbol of her star power, replicated in fancy dress costumes to this present day.

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Versace bodysuit, 2023

Jumping from her early days to her 2023 tour - The Celebration Tour - Madonna is still on top and still taking bold risks. For her 2023 tour, Madonna wears this form-fitting Versace bodysuit, made from a mosaic of glitterball-style mirrored plates.

Worn with flowing blonde locks, Madonna's defiant and powerful image - with the Versace suit almost looking like body armour - is made even more iconic because of the context. In early 2023, the pop legend had a health emergency which left her in the hospital. But, after a short delay, she kicked off her tour to rave reviews, proving she's here to stay.

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Pink hair, 2023

Madonna turned 65 in 2023, and the fearless icon who has never followed society's rules decided to switch up her image to something not necessarily expected for someone in their mid-60s.

In early 2023, the singer debuted a new pink hairdo, and was seen showing off her colourful tresses with a selection of street-style inspired looks, including super on-trend oversized jeans and sportswear.

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Madonna does disco, 1993

Another memorable outfit from The Girlie Show, Madonna donned this 1970s inspired outfit for a section of the tour inspired by Studio 54. With a blonde afro wig and flared velvet trousers, she looked every inch the disco diva.

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Madonna in double-denim, 1998

One thing Madonna doesn't get the full credit for is establishing an artist's "era" - that is, with each new project, she did more than switch up her sound, but she embraced a whole new look and way of being for a time.

One massive switch the Queen of Pop made came in 1998, just a few years after shocking the world with sex books and exposed breasts, she suddenly embraced a more down-to-earth aesthetic, including this double-denim look from the Ray of Light video.

Often considered a fashion no-no, Madge made it cool to rock the double-denim.

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Cowgirl Madonna

A few years after she made double-denim cool again, Madonna first embraced a Western look complete with cowboy hats and boots for the Music album in 2000. While she wasn't the first artist to go (wild) west, she made the look so iconic that she'd later revisit this for an appearance alongside Miley Cyrus in 2022.

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Mrs Guy Ritchie, 2000

Around the same time she first started wearing cowboy hats and denim, she also got married to British director Guy Ritchie in 2000. Proving that she loved sticking to a theme, she continued dressing down and matching the relaxed energy of her cockney husband, sporting casual jeans, a new choppy hairstyle and a ripped t-shirt in support of his new movie.

Madonna and Guy were married for eight years and welcomed son Rocco Ritchie in August 2000.

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British countryside Madonna, early 2000s

Throughout Madonna's marriage to Guy Ritchie, the singer went through something of a British rebirth. Long gone were the shocking outfits and instead, the Queen of Pop started dressing a bit like the Queen of England, wearing tweed jackets and flat caps.

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Prim and Proper, 2000s

Another example of a more conservative Madonna, this floral dress - which you could imagine being worn by the likes of Kate Middleton or Duchess Sophie - was worn to promote her 2003 children's book, The English Roses.

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Madonna in Gucci, 1995

It was a memorable night in 1995 for many reasons. One was Madonna and Courtney Love having an awkward run-in (YouTube it!). The second was seeing the Queen of Pop wear a piece from the reigning king of fashion at the time. This blue satin shirt was from Tom Ford's 1995 collection for Gucci. It was considered his first major collection for the house - or it was "when he arrived", to use the expression.

Kate Moss first wore the same shirt for the runway presentation.

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Madonna goes goth, 1998

At the 1998 VH1 Fashion Awards, Madonna marked a huge departure from her signature styles. Swapping her blonde ambition for maven black locks, she also wore a structured, elaborate yellow corseted gown from Belgian designer Olivier Theyskens.

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Sari, 1998

At the same event she donned the corseted yellow gown, Madonna changed into this traditional sari get-up backstage. From the spiritual attire to the loose black curls, Madonna was certainly making a point that she had begun a new era - one more reflective, mature and removed from her wilder past.

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The red Kimono, 2000

Madonna teamed up with Jean Paul Gaultier in 2000 and recreated a similar style to her music video, Nothing Really Matters.

The multiple Grammy-winning legend donned a striking red kimono, contrasted with her sleek dark hair, white face, red eyeshadow and red boots.

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Re-Invention World Tour, 2004

She was never afraid of making political statements - after all, urban legend has it she's been excommunicated by the Catholic Church THREE times - and she decided to speak out against the war in Iraq during her 2004 world tour.

Suiting and booting in military apparel, this was a major look with an even bigger statement behind it.

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The Evita era

Not content with being the biggest pop star in the world and a cultural juggernaut, in 1996 she turned her hand to serious acting, embodying the role of political figure Eva Peron in Andrew Lloyd Webber’s musical movie, Evita.

She earned herself a Golden Globe - and treated fashion fans to a host of red-carpet looks inspired by the flair of the Argentinian politico. Think feathers and vibrant colours, like this Christian Dior ensemble for the world premiere.

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Madonna gets crucified

Perhaps earning one of those rumoured three excommunications, Madonna (once again) shocked the world when she opened her world tour on a replica of the crucifix. With an actual crown of thorns atop her blonde curls, this was a look for the history books.

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Madonna and Michael Jackson take the Oscars, 1991

Madonna is the best-selling female artist of all time. Michael Jackson is the best-selling male. She's the Queen. He's the King of Pop. And in 1991, these two icons collided when they were each other's date for the Oscars.

Not even Hollywood's brightest could compete.

Madonna channelled Marilyn Monroe with a full Golden Age inspired look, complete with Bob Mackie dress and fur stole. Decked out in diamonds with her platinum blonde locks shining just as bright, Madonna also performed the song, Sooner or Later, on the night.

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Classic Madonna with a twist, 2009

By 2009, Madonna had divorced Guy Ritchie and her family was expanding. Her looks began to adapt around this time, and we see it best with this elevated take on a Madonna staple. There's the corsets and the cross - plus the touch of lace in the bodice - but it's notably more reserved.

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A touch of Hollywood glamour

Madonna turned up to the 2008 Cannes Film Festival looking like Old Hollywood royalty. In a 1920s-style Chanel flapper dress made from black and white sequins, the Like a Prayer singer offered up refined glamour.

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Louis Vuitton, 2008

While attending an event for the launch of Gucci's Tattoo Heart collection, Madonna didn't go with a design from the Italian house, instead opting for an emerald, feather fantasy from the Louis Vuitton Spring 2009 collection.

Some suggested she was looking more like the Grinch or a piece of astroturf, but the subtle touches of a figure-enhancing belt and showcasing her legs with fishnet tights gave this look a fashion thumbs up.

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Old Hollywood glam, 2007

Proof that she can still capture attention with a more straightforward formal look, Madonna's look for the 2007 Vanity Fair Oscars Party was pure glamour. The Queen of Pop wore a chic black gown with straps and Rita Hayworth-inspired hair, and her accessories included glittering bracelets and a silver clutch.

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Shining in satin, 2011 Met Gala

The 2011 Met Gala's theme was Alexander McQueen: Savage Beauty, and Madonna's look definitely focused more on the beauty than the savage.

Dressed in an elegant Stella McCartney satin dress with flower detailing, she completed her look with vintage Cartier jewels (which, fun fact, would later feature in the movie she directed about Wallis Simpson, titled W.E) and a Christian Dior clutch.

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Boy Scout Madonna, 2013

Critics often take aim at Madonna's apparent obsession with youth, but did she take it too far dressing like a Boy Scout? Not quite.

The outspoken icon dressed in the American Boy Scout uniform for an important reason in 2013, challenging the organisation's ban on LGBT youth.

“I wanted to be a Boy Scout, but they wouldn’t let me join,” the singer said at the GLAAD awards. She added, “I think they should change their stupid rules, don’t you? It’s 2013, people. We live in America, land of the free and home of the brave?"

Several years into her career, Madonna was still making huge statements - and that's why this look is forever immortalised.

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Madonna's disco leotard era, 2004

Madonna was in her mid-40s in 2004. Many had counted her out as having hit her peak. After all, pre-Madonna, pop stars tended to have a short shelf life. Naturally, she had something to say about that.

In what many consider one of the greatest comebacks in pop history, Madonna topped the charts across the globe and sparked a whole new fashion craze once again when she donned a purple leotard for her disco-infused album, Confessions on a Dance Floor.

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*That* 2023 Grammys appearance

This one is one of Madonna's most memorable looks, but not necessarily for all the right reasons. Appearing in an androgynous suit and tie, with her trademark blonde locks dyed auburn and her eyebrows bleached, the reaction to Madonna's appearance at the 2023 Grammys sparked headlines across the globe, as many dubbed her unrecognisable.

It was another moment for the pioneering pop legend to make a stand against ageism and the pressures women face.

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Madame X, 2019

In 2019, Madonna released her 14th studio album, Madame X. With the album - inspired by her life in Portugal as her son, David, pursued his football career - came a new persona, also named Madame X. This version of Madonna came with an eye patch. Yes. An eye patch. Only Madonna could turn the pirate accessory into a chic style statement.

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Suited and booted with son, David Banda

Madonna and David Banda delighted fans at the 2014 Grammys by showing up in matching Ralph Lauren suits accessorised with diamond brooches and brimmed hats. Madonna completed her look with an actual cane, for a touch of Italian Mafia magic.

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Madonna is the undisputed Queen of Pop - but she's also fashion royalty, setting trends and breaking rules.