Hisako was the daughter of a wealthy saké brewer, and grew up in Kyoto. After graduating from the Kyoto Prefectural Second Girls' High School, and gaining an interest in painting, and in waka, she studied painting under Kikuchi Keigetsu; Hisako and her fellow students Ôtani Chigusa and Wake Shunkô were together known as the "three accomplished ladies" of Keigetsu's studio.
For a time, she resisted getting married, seeing this as an impediment to her artistic career.
In 1918, the first Kokuten (National Exhibition) was held, and her painting "Train Station in Early Evening" (kureyuku teiryûjo) was one of only 16 selected for inclusion out of 278 submissions from all across Japan. The painting depicts a woman in contemporary Japanese clothing (kimono), sitting on a bench at a train stop, the plain wood of the structure visible in the background. She leans on her umbrella, fatigue evident in her face, and in her posture. Like most of Kajiwara's works, it is masterfully done, and the woman is quite beautiful; but, in contrast to traditional bijinga, Kajiwara's works tend to show the women as real people, tired, dissatisfied, or otherwise possessing of thoughts and emotions, rather than being idealized aesthetic objects.
She continued to submit works to the Teiten (Imperial Exhibitions) in the 1920s, and had many works selected, though rarely were they among the top favorites of the selection committee. Her father fell victim to the global depression after 1929, and went bankrupt; Hisako turned to producing paintings more guaranteed to sell commercially, creating works containing less social controversy or commentary. She returned to including social commentary in her works after the war, and continued to submit to the Kokuten through 1985, just three years before her death. Many of her paintings sold, but many remained in her own possession, with a great number of Taishô era paintings being found in her home following her death in 1988.
- "Kajiwara Hisako." Nihon jinmei daijiten 日本人名大辞典. Kodansha, 2009.
- Morioka Michiyo and Paul Berry. Modern Masters of Kyoto. Seattle Art Museum, 2000. pp292-293.
- An art-name, changed from her given name 久, also pronounced "Hisa."
- 三閨秀 (san keishû)