Polly Willcox also described Miss Hillard’s manner as one of “formality over deep empathy.” She elaborated: “She drew people to her in spite of her formality. There was no feeling of forbiddingness. She was very open and warm. And extremely perceptive. You felt transparent in her view.” The headmistress’s insight was a trait that was also noticed by pupils at Miss Porter’s in the 1880s, as well as by members of the last graduating class she knew at Westover in the early 1930s. When she stood outside the chapel after evening vespers services to say good night to each pupil, every girl felt as if she was looking right through them. (Some teenagers found this so disconcerting that they tried to make their minds blank when they walked by.) Polly went on: “So many of her talks and lectures were so helpful. They made you realize what was the right thing to do and always put you on the right track.”
Many girls found that being away from home was a way to discover themselves. An editor of The Lantern wrote in 1924 that the purpose of boarding school was to find where one’s abilities lay—whether they were intellectual, athletic, artistic, or as leaders—and to develop them, with the effort being more important than the achievement. As their headmistress created an enriched environment by continually quoting Heraclites, Aristotle, Plato, Moses, and Shakespeare, as well as theologians, poets, and novelists, pupils also felt that they were part of something greater than themselves. Life at Westover had a feeling of “great dignity,” in the words of Polly Willcox. It was “formidable, imposing, benign, friendly, supportive,” she added. “I think it was a splendid school, and I loved it very much after the first year.” (Not everyone had her attitude and adaptability, however, and a classmate, who stayed only one year, disliked the aura of “Victorian sentimentality that made me not only figuratively but actually sick.”)
There was nothing unintentional about what Mary Hillard was trying to do: she wanted the young girls placed under her wing to mature emotionally. She talked again and again about the need for them to develop what she called spontaneity—the ability of a teenager to shed self-consciousness and to become herself. It was the way French diplomat Alexis de Tocqueville had described the surprisingly frank voice of the American girl in the 1830s: she “has scarcely ceased to be a child when she already thinks for herself, speaks with freedom, and acts on her own impulse,” he wrote in Democracy in America. The headmistress believed it was a matter of reawakening an earlier naturalness before inhibition set in, the same phenomenon among adolescent girls that Harvard psychologist Carol Gilligan would describe many decades later in her book In a Different Voice. It was, in fact, a pivotal part of Mary Hillard’s educational philosophy that adults should create the conditions for youths to heal and, in other words, “to be trained by us to be free.” This process of personality development could only happen in a small caring community like Westover, she believed, a place that celebrated familiar traditions and provided new experiences.
Among the girls the headmistress understood very well was her niece, Phyllis Fenn, the daughter of her younger sister Emily. Aunt Mary had “many times been the guardian angel of the family,” according to their older sister, Martha, by taking a strong interest in Phyllis and in Martha’s daughter, Ishbel MacLeish, as well as in her numerous nephews. After Phyllis’s first year at Westover in 1920, however, her mother wrote a worried letter to her sister saying that her only child was no longer lighthearted. In her reply, Mary said that at school Phyllis was “bubbling over with interests and fun,” and that it was a “tremendous” transition to go from school to home in the summer. She also elaborated on her theory about female development, writing that the maturity of girls depended on “shattering their self consciousness” by using their minds. In her letter, she wrote that Phyllis should think “how someone she dislikes would act in [a] situation—for she is free of self in thinking of someone she dislikes and how she would act. It is all a matter of using one’s brains and recollecting how little other people are ever thinking of those about them—any more than we are thinking of those about us”. She reassured her sister that it was natural for teenagers to be moody and melancholy, and she predicted that Phyllis would go through many other stages. All adults can do is to create wholesome conditions for them, her aunt wrote, and then “let them grow! Mother Nature is wiser than we are. Leave it to her. The flower too goes through many phases before arriving at bloom and fruitage.” She added: “If you could hear how every mother with her first daughter is astounded, dismayed, perplexed and discouraged you would take comfort.”
A year and a half later, Phyllis’s aunt decided that her niece was ready for a glamorous evening gown and a more sophisticated social life. “Aunt Mary has given me a new party dress!!!!!” Phyllis wrote to her mother. “It is a heavenly shade of blue with silver on it. It is rather of a turquoise blue and is chiffon with ends floating from it all around!!!” The aunt and niece then planned to go together to New York City to a Westover friend’s debutante dance at the Metropolitan Club. “Aunt Mary said she didn’t know whether I would have a good time, but it would add to my experience anyway,” the girl confessed to her mother.
Miss Hillard also freely gave advice to other parents about how to bring up their daughters. In a letter to the father of young Betty Choate, she first praised the girl’s personality, but then politely stated that she was immature and needed to spend a year in Europe. The headmistress also bluntly said that he and his wife should spend more time with their daughter. Many times, in fact, she advised parents to become less distant dominating figures and be better friends with their children. Speaking of all young people, she rhetorically posed a question to parents on Visitor’s Day in 1923: “How can you help them?” And then she gave the answer: “Give up authority—that was only to protect them. Substitute companionship,” she said, and “enter into their troubles and their ambitions.”
Girls encircling the West apple tree inside the Quad. WESTOVER SCHOOL ARCHIVE.
While the principal preached to parents, she also scolded pupils from time to time. She was strict about decorum, especially in the dining room, and girls rarely tried to defend themselves. When a spider dropped down the front of a new girl’s dress during dinner one time, she let out a cry. Everyone in the dining room became silent, and Miss Hillard told her to go to her sitting room after dinner, where the girl was informed about the time a mouse ran up another girl’s leg in chapel, but she remained silent and held onto it until the service was over. When the headmistress was dismayed by what she perceived as a diminishment in the spirit of the school, she would start what were called “reigns of terror” that lasted for days. In February of 1912, for instance, she went to the schoolroom “with trouble written all over her face” to talk about a prank the day before, when girls had dressed up a dummy in a uniform to fool a new teacher. Miss Hillard told the assembled school that the joke had, in the words of a student, “hurt her pride in the girls so [much] that she kept from breaking down before us only with the most heroic effort,” Jessica Baylis wrote to her parents. Then the headmistress asked those involved to stand up, and when they did, she spoke to them sternly.
A troubling aspect of Miss Hillard’s personality was her tendency to favor some girls over others. She evidently liked leaders and well-rounded students, partly because they were excellent examples to others. She begged the mother of Rachel Latta to send her daughter back to Westover after a year abroad, and when she did, Miss Hillard wrote that “I am glad for Rachel, and deeply glad for