Ann “Heady Lady” Di Benedetto
Ann M. Di Benedetto was Cleveland’s unforgettable “Heady Lady,” a milliner whose passion for fashion transformed a personal love of hats into a celebrated cultural legacy. As the owner of Heady Lady Millinery, Ann curated a dazzling personal collection of more than 500 hats, each with its own story. Her designs were worn by presidents, first ladies, and fashion enthusiasts across the country, reflecting her flair for elegance and her belief that a hat was never just an accessory—it was a statement.
Crowned Mrs. Cleveland in 1967, Ann became a beloved public figure, traveling nationally to present her lively hat shows in Cleveland, Palm Beach, and Boca Raton. These events blended fashion, storytelling, and philanthropy, raising funds for causes close to her heart, including the American Red Cross and the Christ Child Society.
Our temporary exhibit celebrates Ann’s extraordinary eye for style, her decades-long influence on Cleveland’s fashion community, and the joy she brought to audiences through her unforgettable hats. Each piece on display honors her creativity, generosity, and the vibrant spirit that made her a true original.