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Once upon a time, the Academy Awards were a rather innocent event. The first were held in 1929, and took place at a private dinner at the Roosevelt Hotel. The recipients of the prizes were announced three months in advance. Janet Gaynor wore a sailor look she had bought off the rack at a department store when she won best actress honors for her trio of performances in 7th Heaven, Street Angel and Sunrise: A Song of Two Humans. Gaynor later consulted on her clothes with her husband, Gilbert Adrian, a costume designer best known for his work with Joan Crawford.

In 1937, German-born Luise Rainer won the best actress award for playing Florenz Ziegfeld’s common-law wife, Anna Held, in the 1936 film The Great Ziegfeld. Rainer would win back-to-back best actress awards, for playing the Chinese peasant O-Lan in the 1937 film of Pearl S. Buck’s The Good Earth. On the evening of the 1938 Oscar presentation, she got into a big fight with her then-husband, the left-wing, ultra-high-minded playwright Clifford Odets. The pair were driving around and around the block where the event was being held. She finally went in and accepted her Oscar wearing a sweater dress — and was criticized in the press for her somewhat low-key outfit.

The award also arguably cut short her career, since there was a substantial backlash against the same relatively unknown actress consecutively winning two of the earliest Oscars for best actress in a leading role. Greta Garbo was the favorite that year for Camille. (Rainer had the last laugh—literally; she married a wealthy man, publisher Robert Knittel, in 1945 and died late last year just two weeks before her 105th birthday.)

Snarky remarks about awards-show fashion thus began early. The Oscars were notable for great looks and less-great ones. There were remarkable fashion collaborations to be seen, such as Hubert de Givenchy and Audrey Hepburn, and Edith Head with Grace Kelly.

Then there are the very bad awards-show looks, which everyone seems to enjoy most. Fashion pundit Richard Blackwell’s Worst-Dressed List was launched in 1960, and many notable actresses—starting with Anna Magnani and including Julie Andrews, Sophia Loren, Ali MacGraw, Meryl Streep, Julia Roberts and many more—found their way to the top.

WWD, which created the “Who are you wearing?” query, had plenty of fun skewering  red carpet and other fashion mishaps, too. Strange and silly outfits, such as Barbra Streisand’s 1969, see-through sequined Arnold Scaasi pantsuit; Cher’s 1986 Indian princess look by Bob Mackie; Demi Moore’s curious 1989 bicycle pants, bustier and brocade pannier ensemble, Kim Basinger’s 1990 white satin ballgown with a half-jacket, which each said she had “designed myself”; Geena Davis’ 1992 ruffled cutaway ensemble by costumers Ruth Meyers and Bill Hargate; Juliette Lewis’ 1992 cornrows; Celine Dion’s 1993 worn-backward, white Dior pantsuit and hat—which occasioned so much ridicule that she reportedly no longer appears on red carpets—and Björk’s startling swan dress by Marjan Pejoski of 2001—which some observers called a fashion foul but, to be fair, was loved by many—fueled the hilarity.

Red-carpet coverage was transformed in 1994, when Joan Rivers and her daughter, Melissa Rivers, began reporting live from the scene, taking snarky shots at celebrities, famously saying things to the camera that everyone else was thinking. Rivers once said, “The worst fashion crimes are always the best. Everyone remembers Björk’s dying swan and Moore’s cycling-shorts ensemble. The real crime is not being outstanding. If I really wanted to be noticed, I’d wear the dying-swan thing.”

The style ante was upped considerably when Giorgio Armani got into the game in 1989, trying to bring order to the proceedings by hiring Wanda McDaniel as his L.A. celebrity liaison. It worked. As a journalist for publications including the Los Angeles Herald Examiner and the L.A. Times, and the wife of film producer Al Ruddy, McDaniel knew most of Hollywood and quickly got Armani on the backs of many top and rising stars.

Other designers and firms, peddling everything from evening dresses to handbags and jewelry, swiftly followed suit. Conservative looks reigned in the Oscar ceremonies during World War II and the first Oscar ceremonies after 9/11, in the spring of 2002. Now it’s common to opine (and WWD’s own fashion critics do it) that the red carpet has become too dull and too safe.

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