The psychological aspects of propensity to offend are considered. The relationship between attitude, personality, and reported offending is explored. Some literature considers how attitude influences offending; others look at the relationship between personality and offending. The present thesis proposes that there is a complex relationship between all three. The Attitude to Offending Style Scale measures preferences towards hypothetical offending styles. Shultzs’ FIRO-B explores the structure of interpersonal personality. Finally, an adaptation of Youngs’ D42 (D45) explores styles and level of reported offending. 254 members of the general public complete each of these self-report scales. An SSA-I tests the construct validity and structure of the scales stated above. Multiple regression analyses explore the relationship between attitude and personality, and how these influence level of reported offending. The moderating role of interpersonal personality is also considered. The findings reveal that Attitudes are categorized as: Instrumental or Expressive high risk, and Low risk. Shultzs’ FIRO-B scale has four facets: Expressed Inclusion Expressed Control, Received Inclusion and Received Control. Finally, reported offending is categorised as More or Less serious, Instrumental or Expressive, and target Person or Property. Results show that variations in attitude and personality styles are related to level of reported offending. Furthermore, it was found that the relationship between attitude and level of reported offending is moderated by level of ‘Received Control’. More specifically, when an individual shows a positive attitude towards Instrumental high risk crimes and feel ‘controlled by others’, their level of reported offending is also likely to be high. The presented research shows the value of considering attitudes towards offending, the moderating role of interpersonal personality, and how this relates to level of reported offending. The methods employed throughout the thesis demonstrate the strength and validity of self-report measures. Results are applicable to many areas, including direction and methods in future research. The findings can be applied to areas such as rehabilitation, interview techniques and preventative measures.