Assessments and predictions of driving behavior are very important to improve traffic safety. We hypothesized that there were some patterns of driving behaviors, and these patterns had some correlation with cognitive states and personalities. To test this hypothesis, an evaluation of driving status, based on electroencephalography (EEG) and steering behavior in a simulated driving experiment, was designed and performed. Unity 3D was utilized to design the simulated driving scene. A photoelectric encoder fixed on the steering wheel and the corresponding data collection, transmission, and storage device was developed by Arduino, to acquire the rotation direction, angle, angular velocity, and angular acceleration of the steering wheel. Biopac MP 150 was utilized to collect the EEG data simultaneously during driving. A total of 23 subjects (mean age 23.6 ± 1.3 years, driving years: 2.4 ± 1.6 years, 21 males and two females) participated in this study. The Fuzzy C-means algorithm (FCMA) was utilized to extract patterns of driving behavior and the cognitive state within the window width of 20 s. The behaviors were divided into five kinds, i.e., negative, normal, alert, stress, and violent behavior, respectively, based on the standard deviation of steering wheel data. The cognitive states were divided into four kinds, i.e., negative, calm, alert, and tension, respectively, based on the EEG data. The correlation of these data, together with the personality traits evaluated using Cattell 16 Personality Factor Questionnaire (16PF) were analyzed using multiclass logistic regression. Results indicated the significance of the cognitive state and seven personality traits [apprehension (O), rule consciousness (G), reasoning (B), emotional stability (C), liveliness (F), vigilance (L), and perfectionism (Q3)] in predicting driving behaviors, and the prediction accuracy was 80.2%. The negative and alert cognitive states were highly correlated with dangerous driving, including negative and violent behaviors. Personality traits complicate the relationship with driving behaviors, which may vary across different types of subjects and traffic accidents.