The Biggest Fashion Disasters of Award Shows

Awards ceremonies have a kind of magic. The brightest stars in Hollywood come together to walk the red carpet and show off incredible looks from the best designers in the world—except sometimes those looks aren’t so incredible. While taking a risk can certainly pay off, it often earns celebrities a spot on a worst dressed list. At least we can always say these looks were unforgettable.

Demi Moore’s 1989 Oscar Dress

Demi Moore’s 1989 Oscar Dress

While Demi Moore’s red carpet looks are usually chic and sophisticated, the St. Elmo’s Fire and About Last Night… star couldn’t escape the 1980s without one major fashion disaster. Moore showed up the 61st Annual Academy Awards with Bruce Willis looking a lot like she’d biked to the theater.

For the ceremony, Moore decided to try her hand at fashion design, and it’s safe to say she should stick to acting. The bizarre ensemble featured lace-trimmed bike shorts and plunging floral bustle. We do have to give Demi props for one things: we’ve never seen another Oscar dress like this one.