Objective: This study investigated users’ subjective evaluation of three highly automated driving styles, in terms of comfort and naturalness, when negotiating a UK road in a high-fidelity, motion-based, driving simulator. Background: Comfort and naturalness are thought to play an important role in contributing to users’ acceptance and trust of automated vehicles (AVs), although not much is understood about the types of driving style which are considered comfortable or natural. Method: A driving simulator study, simulating roads with different road geometries and speed limits, was conducted. Twenty-four participants experienced three highly automated driving styles, two of which were recordings from human drivers, and the other was based on a machine learning (ML) algorithm, termed Defensive, Aggressive, and Turner respectively. Participants evaluated comfort or naturalness of each driving style, for each road segment, and completed a Sensation Seeking (SS) questionnaire, which assessed their risk-taking propensity. Results: Participants regarded human-like driving styles as more comfortable and natural, compared with the less human-like, ML-based, driving controller. However, between the two human-like controllers, only the Defensive style was considered comfortable, especially for the more challenging road environments. Differences in preference for controller by driver trait were also observed, with the Aggressive driving style evaluated as more natural by the high sensation seekers. Conclusion: Participants were able to distinguish between human- and machine-like AV controllers. A range of psychological concepts must be considered for the subjective evaluation of controllers. Application: Knowing how different driver groups evaluate automated vehicle controllers is important to design more acceptable systems in the future.