The Gist
Demi Moore sat down for a new interview with WWD.
She discussed her polarizing look at the 1989 Oscars.
Moore designed the ensemble herself.
Demi Moore has few fashion regrets—but one outfit still haunts her to this day. In a new interview with WWD, the Landman star revealed her true feelings about perhaps her most controversial look to date.
Moore famously DIY-ed her look at the 1989 Oscars, which consisted of a corset and half-skirt layered over biker shorts. The ensemble landed her on many ‘worst dressed’ lists at the time.
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Demi Moore with Bruce Willis at the 1989 Oscars.
“ I’ve been collecting vintage clothes since I was 15 years old, and I’ve gone through a variety of looks. Probably some disasters, some things where I could say, ‘Oh, maybe I was a little ahead of my time. Maybe I didn’t quite execute it,’” Moore shared.
“Do I feel a little bit of that embarrassment that comes over the biker shorts? But I think about that now and I think, well, if there was a version of that—and maybe actually there has been somewhat of a version of it—in our current times, that it wouldn’t seem so out of the box,” she continued.
” I think when we’re younger, it’s a combination of also finding ourselves, and so there’s a lot of trial and error. And even today, the reality is we can do our best to approach it the same every time, but we’re not gonna always hit it out of the park,” Moore concluded. “It’s also knowing to not put too much stakes on what the outside response is when I walk out the door.”
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Demi Moore on November 11, 2025.
Last fall, the actress suited up to star in a new National Football League promo. In November, she uploaded an Instagram video in which she sports a sparkling blazer.
“The story of rivals. Oil and water, chemistry and chaos. As it’s always been… as it will always be @nflonfox 🏈🛢️ @landmanpplus,” the caption of her post read.
Moore’s fitted jacket, covered in crystals, also came with the addition of a trendy accessory: the brooch.
Demi Moore/Instagram/NFL
Demi Moore in an Instagram video posted on November 25, 2025.
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