Gwendolen was greatly influenced by her in-laws, who moved in a very prominent social circle, yet opted to spend the majority of their time in the relaxed atmosphere of their estate along the Hudson. Edward and his siblings enjoyed a childhood in the country surrounded by their father's peach orchards, working in his stained glass studio, and enjoying the company of his eclectic circle of artistic friends. In her unpublished memoir, Edward's sister, Helen writes of clothing:
“Mama never bothered us about little things. Maity (Edward) wore a kilt, and with it always a belt, a tin sword, and a rabbit’s tail sewed on his jacket at the back. This with a Glengarry cap and his long blond hair made him quite picturesque, but he didn’t look odd to us. I knitted myself a belt and a sort of pocket of red worsted. I used to fill this with berries and walk slowly around the garden eating them….I wore a pink and white wrapper, long, with pink frills down the front; with my red worsted belt and pouch I must have looked funny but no one told me so.”
Gwendolen's brother in-law, Hamilton, offers commentary, which also discloses certain ambivalence towards prescribed sartorial etiquette. In his published memoir, Those Days, he writes:
“If I describe how the girls’ dressed–middy blouses, wide pleated serge skirts, black stockings, hair tied with bows-they will sound like a basketball team from a reformatory. I can only say that to us they were beautiful. Even when camping the bathing costumes were more decorous than decorative…The girls were completely covered in black or navy blue…Frilly sleeves extend almost to the elbows. The bloomers were not visible, except by mischance, for the skirts covered them to below the knees. The bloomers joined long black cotton stockings. Unlike less emancipated creatures at Bailey’s Beach in Newport, however they did not wear black gloves or straw hats in the water.”
Gwendolen's writings after her marriage reveal a bustling, busy, less constrained social life. The world of Gwendolen's adulthood had rapidly changed and the grand traditions of her upper class upbringing were falling by the wayside. The balls and parties of the early years of the Gilded Age became outdated. Gwendolen seemed happy to wear the ready-made, stylish, and neat clothing adopted by her middle-class contemporaries. This clothing allowed her to travel easily about town and participate in a wide variety of social and sporting activities. Gwendolen's lighthearted personality, athleticism, and wide social circle no doubt allowed her to make a welcome and harmonious transition to modernity.