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The man in the mirror: Michael Jackson’s most magical looks

Marking the release of Xscape, Sony’s second album of previously unpublished Michael Jackson tracks, we honour the regal wardrobe of the King of Pop. If there ever was an appropriate time to use to the word iconic, it would be to describe Michael’s look: part Napoleonic warlord and part dapper gangster, his dressmaker for life Michael Bush once his described his larger-than-life client’s wardrobe as “Liberace goes to war”. Through his clothes – clothes, not costumes – Michael fashioned himself into a walking wonder, a fairytale king, and an optical illusion all at once. Everyone has their favourite Michael Jackson look and that’s the power of his all-embracing appeal. But beyond the classics – the Billie Jean glitter outfit, the Smooth Criminal gangster suit, the HIStory Tour gold ensemble – Michael donned some pretty breathtaking lesser-known numbers. We give you five that rocked our world.

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Text Anders Christian Madsen
Image Annie Leibovitz for Vanity Fair

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  • The Privy Councillor Diplomatic Uniform

    While Michael occasionally worked with fashion designers – Gianni Versace, Roberto Cavalli, and Christophe Decarnin to name a few – he wasn’t a huge fan of fashion. For Michael, clothes were about dreams: making them up, having them made, and wearing them first. As a result, it’s hard to come by a Michael Jackson outfit that wasn’t made by Michael Bush and Dennis Tompkins under Michael’s meticulous supervision, unless of course Michael happened to see something in a shop window. That’s what led to the first look on our list, the Privy Councillor Diplomatic uniform by Gieves & Hawkes. During his Bad tour in the late 80s, Michael spotted it in the master tailor’s Savile Row window and called upon Gieves & Hawkes cutter Garry Carr to make him his very own. Carr got ten minutes with Michael in his hotel room, Michael asked for various extras to be added, and his first (and possibly only) real military uniform was created. He wore it for a Vanity Fair shoot with Annie Leibovitz, and just like that he moved on to the next one.

  • The In the Closet Look

    When you think of Michael Jackson in a style context, fantastical military jackets and magic dust are usually the first things that come to mind. And that’s the way he would have wanted it. But maybe that’s the reason one of his strongest looks ever was also his perhaps most toned down. For his In the Closet short film directed by Herb Ritts, Michael was chasing Naomi Campbell around a hacienda in the Californian desert. It was hot, dusty, and stripped down to the essence of Michael Jackson’s magic: the moves, the body language, and the inimitable sex appeal. Michael wore his super skinny, custom made black Levi’s 501s, a sleeveless white vest with a deep v-neck, and suede Chelsea boots – the latter being a rare choice for Michael, who usually only danced in his trusted Florsheims. His hair was straightened and worn in a ponytail, streamlining a look, which was all about Michael’s slender silhouette and supernaturally flexible limbs. You cannot wet it, you cannot burn it.

  • The HIStory Teaser Uniform

    Michael’s perhaps most extravagant project, the HIStory Teaser was a promotional short film for its namesake album. Filmed in Budapest with more than a hundred British soldiers, hired by Michael as his private army for the shoot, the film called for his most lavish uniform to date. His tailor Michael Bush hasn’t disclosed a lot of details about the uniform or the film, and much of it is still veiled in the kind of mystery of which Michael was a champion. But if the presence at the shoot of Gottfried Helnwein – the Austrian-Irish artist, who deals in social commentary based on imagery of mistreated children and fascist regimes – is anything to go by, this uniform had its roots in the machine-driven wars of the twentieth century. Parts of Michael’s aesthetic during the HIStory era dealt with futurism (take Scream and the tour costumes, for instance), and in the HIStory Teaser, he merged all his wardrobe inspirations to perfection. Not an inch of the uniform was left un-embellished, from the silver breastplates and arm plates to the customised MJ army insignia, gilded Wayfarers, and shiny black leg guards.

  • The Presidential Uniform

    The year was 1990. George Bush Senior might have been president of the free world, but it was Michael who ruled it. Case in point: when he went to the White House to pick up his Artist of the Decade award, Michael wore a black hussar jacket with black embroidery, black military trousers with a red stripe down the thigh, and a matching red and black cummerbund. President Bush? Some sort of suit and tie. Michael used the occasion to debut the latest challenge he’d given the dressmakers of his royal court: a steel sabaton prototype of a pair of sterling silver greaves he’d commissioned with the idea that he wanted to wear boots, which looked and moved like medieval armour. When Tompkins and Bush (the dressmaker, not the president) finally finished the sterling silver greaves, Michael only ever wore them in a photo shoot. At seven and a half lbs, they were too heavy to walk in. As for the eventual fate of the black hussar jacket, Michael decided to give it to a fan he met in a lift.

  • The Pearl Jacket

    Michael Jackson’s all-time favourite jacket (he said so himself) was designed by Michael Bush and Dennis Tompkins, who drew inspiration from the pearls of the jackets of Henry VIII. Michael wore it to the 1993 Grammy Awards with a white deep v-neck t-shirt, black Levi’s 501s, and extra-heeled black Chelsea boots, which matched his black suede gloves. With Michael’s glistening black locks and snow-white skin, he was the king of the two-tone look, and he never reigned as absolute as that night at the Grammys, with Brooke Shields as arm candy. When Janet presented him with the Legend Award, Michael pulled his sister over and quipped, “I hope this finally puts to rest another rumour that has been in the press for too many years: Me and Janet really are two different people.” Over the years, a lot of Michael’s wardrobe was lost or given away by the King himself, and when, after Michael’s passing, Bush and Tompkins couldn’t find the original, they made a replica, which he wore in the casket.