System for monitoring and classifying driving behavior of an operator of a motor vehicle includes at least one personal monitoring device having mechanism(s) for wearing the device by and/or attaching the device to the operator, and hardware including local memory, battery, and sensors. The device provides at least GPS and communication functions, and monitors and communicates information about driving behavior, including driving data collected by the device without receiving it from vehicle sensors and/or calculated or derived from data collected by the device without receiving it from vehicle sensors. Application software on the device interfaces with device hardware for monitoring and communicating, being activated and deactivated based on trigger events. At least one control system includes an information processor receiving and communicating information about driving behavior, aggregating information, and communicating at least some of the aggregated information. At least one algorithm classifies driving behavior from at least a portion of information gathered by the device.