Restart slideshow

Hollywood's Most Daring Vintage Fashion Moments

8. Loretta Young's Modest Frock
In 1948, Loretta Young won the Best Actress accolade for her role in Farmer's Daughter. She marked the event by wearing a voluminous, emerald-green dress, which had a garland of oversized bows and ruffles running down the length of the skirt. The bright green dress was paired with elbow-length gloves in the same color, creating a fashion-forward picture. (She took off the turtleneck portion of the gown to make it more red carpet friendly.)

The gown was created by Adrian Greenberg, the costume designer behind the fanciful outfits of The Wizard of Oz — including the red-sequined ruby slippers worn by Judy Garland. He was also the designer behind hundreds of Metro-Goldwyn-Mayer films between 1928 and 1941, so he had a close relationship with many of Tinsel Town's top actors, including Young.