Automated driving has the potential to improve the safety and efficiency of future traffic and to extend elderly peoples’ driving life, provided it is perceived as comfortable and joyful and is accepted by drivers. Driving comfort could be enhanced by familiar automated driving styles based on drivers’ manual driving styles. In a two-stage driving simulator study, effects of driving automation and driving style familiarity on driving comfort, enjoyment and system acceptance were examined. Twenty younger and 20 older drivers performed a manual and four automated drives of different driving style familiarity. Acceptance, comfort and enjoyment were assessed after driving with standardised questionnaires, discomfort during driving via handset control. Automation increased both age groups’ comfort, but decreased younger drivers’ enjoyment. Younger drivers showed higher comfort, enjoyment and acceptance with familiar automated driving styles, whereas older drivers preferred unfamiliar, automated driving styles tending to be faster than their age-affected manual driving styles. Practitioner Summary: Automated driving needs to be comfortable and enjoyable to be accepted by drivers, which could be enhanced by driving style individualisation. This approach was evaluated in a two-stage driving simulator study for different age groups. Younger drivers preferred familiar driving styles, whereas older drivers preferred driving styles unaffected by age.