Smartwatches (SW) are wearable devices that support daily life and monitor an individual’s health and activity status. This information is utilized to promote behavior modification, which could help prevent chronic diseases and manage the health of older adults. Despite being interested in SWs, older adults tend to decrease their SW usage as they age. Therefore, understanding the acceptance of SWs among older individuals can facilitate individual health management through digital health technology. This study investigated the factors associated with the acceptance of SWs among older adults in Japan and the variations in the factors by sex. This study utilized data from the 2022 Itabashi Longitudinal Study on Aging, an ongoing cohort study conducted by the Tokyo Metropolitan Institute for Geriatrics and Gerontology. We included 899 eligible individuals aged ≥65 years. Participants were classified into three groups: possessing SW (possessor group), not possessing SW but interested in possession in the future (interest group), and not interested in possession in the future (non-interest group) using a self-administered questionnaire. The level of SW acceptance was operationally defined as follows: low (non-interest group), medium (interest group), and high (possessor group). Further, we evaluated the association of acceptance and purchase intentions of SWs with sociodemographic variables, technology literacy, and health variables. Among the participants, 4.2% possessed SWs, with no significant sex difference (men, 4.2%; women, 4.3%). Among men, age < 75 years, obesity, diabetes, and dyslipidemia were significantly associated with SW acceptance level. Contrastingly, among women, age < 75 years, living alone, higher household income, and a high score for new device use in the technology literacy category were significantly associated with SW acceptance level. Health-related factors were associated with SW acceptance in men, while technology literacy and sociodemographic factors were associated with SW acceptance in women. Our findings may inform the development of sex-specific interventions and policies for increasing SW utilization among older adults in Japan.