Mess-Dressed List


Some gowns, like Gwyneth Paltrow’s pink Ralph Lauren number at the 1999 Oscars, can launch an emerging star into the stratosphere. Others can leave them crashing and burning. Here, a look at some of the most memorable sartorial blockbusters and bombs. Click here to see more of W‘s fashion scandals.


Lady Diana Spencer’s first formal outing with Prince Charles in 1981 became a fashion coronation when the 19-year-old wore a low-cut black taffeta Emanuel gown, prompting her future relation Lady Diana Cooper to quip, “Wasn’t that a dainty dish to set before a king?”


Madonna toyed with the boys and the markers of feminine respectability in her “Like a Virgin” lace bustier and tutu at the 1984 MTV Video Music Awards.


When Cher showed up to the Academy Awards in 1986 in a jaw-dropping Bob Mackie ensemble and headdress, the template for attention-getting red carpet wear was created.


Punks everywhere snarled when Elizabeth Hurley went as Hugh Grant’s date to the 1994 London premiere of Four Weddings and a Funeral in the infamous black Versace gown held together by strategically placed gold safety pins.


Not all fashion credits are equal, as the Gap found in 1998, when it was revealed that Monica Lewinsky still had the unwashed blue shirtdress (knee pads optional) that bore the semen stain resulting from her intern session with President Clinton.


Lil’ Kim served time for perjury and conspiracy, but many fashion observers wanted her arrested for wearing a breast- (and pasty-) revealing one-armed purple sequined jumpsuit to the MTV Video Music Awards in 1999.


Björk ruffled feathers when she donned a swan dress—complete with a bird head around her neck—by Marjan Pejoski to the 2001 Academy Awards and lifted her plumed skirt to lay an egg on the red carpet.