Barbra Streisand, in 1969
The star of Funny Girl tied for Best Actress (with Katharine Hepburn) and accepted her award in an outfit which, depending on how you look at it, was either a fun nod to the playful fashion of the era, or, as we might say today, a hot mess. Decked out in an Arnold Scaasi bell-bottomed pantsuit that was so sheer under the bright lights of the Dorothy Chandler Pavilion you could see right through it (luckily, it was lined with nude-colored silk), Streisand tripped on her way up to the stage. Unfazed, she more than made up for it during her acceptance speech when, gazing upon her Oscar, she cooed Funny Girl’s most beloved line: “Hello, gorgeous.”