While Walt Disney holds the record for the most Oscars overall, the record for the most Academy Awards won by a woman belongs to costume designer Edith Head. Over her legendary career, Head won 8 Oscars and received a staggering 35 nominations. She worked on some of the most iconic films in Hollywood history, including 'All About Eve,' 'Roman Holiday,' and 'The Sting.' Known for her signature round glasses and straight-cut bangs, she became a celebrity in her own right. She famously served as the inspiration for the character Edna Mode in Pixar’s 'The Incredibles.' Head’s dominance in the Costume Design category remains a benchmark for excellence and longevity in a technical field.