Kim Basinger – 1990 Academy Awards

Fashion is all about mixing different styles into new formats, being inventive, and making a statement. But with every gamble comes risk, and the riskier the move, the higher the chances of losing. And that’s exactly what happened to Kim Basinger at the 1990 Academy Awards.

She attempted to combine two disparate styles by showing up in a half-gown, half-tuxedo dress that certainly didn’t impress her fans. It’s a pity to see such a beautiful woman in such a jarring dress, but we still have to praise her for trying it out.