Cher's Oscar Outfit

Let’s try something. I’m going to say a name, and you’re going to think of the first outfit that comes to mind. Ready? Cher.

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Admit it: you pictured that feathered headdress, that spiderweb–looking top, and the long black, sparkling skirt over the black leather pants she wore to the Oscars in 1986.

If the Oscars ended tomorrow (which I hope not!) and there truly was an end to the ultimate red carpet fashion night, surely Cher’s Oscar dress would make the list. She wasn’t a winner that night—that’d come later—but this was a so-called revenge dress for not nominating her.

Cher had been an awards frontrunner all season long in 1985 for her Cannes-winning role in Mask, but come Oscar nomination morning, her name was nowhere on the list of actresses (Geraldine Page was the long overdue winner). And when you’re a fashion icon, you use your style to tell the story. So when Cher was asked to present Best Supporting Actor, she agreed, and she worked with her favourite designer Bob Mackie on the perfect gown.

Cher and Bob Mackie first met in the ‘60s, when she was working on The Carol Burnett Show. He quickly jumped to doing the costumes for her variety shows and from thereon became her go-to designer. He’d tell Interview magazine in 2018 that Cher “was never uncomfortable in anything—she was very young, and she kind of just wore the clothes like you would a T-shirt and jeans.”

When he says Cher was never uncomfortable in anything, believe him. In fact, just Google it. There are very daring outfits in the Cher lookbook; some that were so jaw-droppingly against the fashion norms of the ‘60s and ‘70s that she ushered in new trends and became a fashion icon as she dominated television with her variety show, music with her many albums, and the world with her street looks. She knew how to push the envelope and how to wear clothing to start conversations. Here’s a great article from the Cher Fan Club website about their relationship; they say it so much better than I ever could.

As Bob Mackie recalled to Vanity Fair: “She said, ‘I don’t want to look like a housewife in an evening gown.’ We never have to worry about that.”

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Looking back at some of her biggest fashion moments in a Vogue featurette, Cher called this one of her favourite outfits. “I came to Bob with an idea. I said, ‘I want to have a mohawk, and I want to do something that’s not actually Indian but I want it to be so over the top that it’s next week. He came back with this… I loved the whole thing.”

She also revealed that her boyfriend at the time swore he’d be fine with whatever she wore, but when he saw her fully-clothed in this, he almost passed out.

“I had the idea mostly because the Academy didn’t really like me, so I thought they hated the way I dressed and I had young boyfriends and they thought I wasn’t serious, so I came out and said ‘As you can see, I got my handbook on how to dress as a serious actress.’”

Mackie said that he’d expressed reservations that Cher, who was only a presenter that year, may pull all the attention away from whoever won Best Supporting Actor that year.

But Cher couldn’t be swayed. “She said, ‘Oh, no. I don’t know who [the winner will] be, but he’ll love it.’” That winner would turn out to be Don Ameche, who would say that he loved Cher’s outfit. Maybe not so much because he loved it, but because it kept him in the papers. “He said, ‘I would not have my picture in every paper in the country with Cher if she hadn’t dressed like that.’”

When Cher did eventually win an Oscar in 1987 for Moonstruck, she again went with Bob Mackie, but it was more toned down—if you can call it that. The naked illusion dress was back, pulling focus towards the middle, with the fringe hanging off the bodice and the fabric coming into a swirl of rhinestone fringe down the centre of the skirt.

Cher told Vogue that she hadn’t expected to win because Moonstruck was a comedy and actors hardly ever win for comedies, so she just wanted to look beautiful. It’s another perfect Cher dress, in my opinion. It would look so over-the-top and attention-seeking if, say, Audrey Hepburn or Gwyneth Paltrow or Jennifer Lawrence wore it; but because it’s Cher, she pulls it off and makes it look elegant.

And honestly, if you haven’t seen some of the other looks Cher has worn to the Oscars, beginning in 1968, you really should. It’s a kaleidoscope of colour and style, the kind only Cher could ever get away with.