In the domain of automated driving the design of automated driving functions remains a crucial factor to achieve high user acceptance. The paper addresses this topic and focuses on the research question whether if drivers prefer their own or at least a similar driving style when driving in an automated mode. Therefore, we conducted two simulator studies investigating overtaking maneuvers under three situations on a two-lane highway in DLR’s dynamic driving simulator. Experiment 1 was conducted to collect manual driving data. We applied the tool CONFORM (Conflict recognition by image processing methods) to cluster the data into four different driving style clusters per situation. In experiment 2, participants of experiment 1 returned and drove an automated vehicle (SAE Level 2) and named their preference among the different driving styles. Most drivers preferred their driving style or a similar one. However, some drivers also preferred driving styles different to their driving style. Driving styles with a small safety margin and high acceleration were disliked by all participants.