Demi Moore was way ahead of the athleisure trend at the 1989 Academy Awards. The ensemble she put together included — gasp! — a pair of Spandex bike shorts. While it can be brave to buck tradition and go where no fashionista has gone before at a Hollywood event, there’s a reason few celebs have attempted to pull off that particular silhouette on the red carpet. Something about the shorts’ weird length just makes it impossible to take them seriously as formal wear. However, Moore made a futile attempt to fancy hers up a bit with some lace trim.

Of her personal style, Moore told InStyle, “I tend to go towards classic with a twist, and I quite love vintage.” We’ve already covered her Oscar look’s twist, and it did, indeed, include a vintage element as well. Her velvet, corset-style bodice would have looked fine paired with a matching skirt, and perhaps Moore knew this in the back of her mind; gold fabric attached to the back of her top created a mullet skirt that was appropriate for the era. Unfortunately, the outfit keeps landing her on worst-dressed lists, including The Sun’s retrospective of “The most awfully memorable Oscar gowns of all time.” Time magazine wrote of the look, “It’s like someone locked her in the Tower of London for months with nothing but a stationary bike and a mood board for company, and the mood board became self-aware.”

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Nicki

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