Women entrepreneurship is a recent phenomenon in India. This study has been conducted to explore the issues of identity and women entrepreneurship from the perspectives of thriving, evolving and prospering small urban India in this millennium beyond the peripherals of metropolis. The study has been to explore the levels of perceptions of identity of women entrepreneurs as businesswomen as well as to ascertain the relationship between perceptions of identity and socio-demographic and family relational factors. The study also tries to find the causal relationship between the business organizational factors and perceptions of identity level of women entrepreneurs as also the cumulative effects of all factors on the levels of perceptions of identity of women entrepreneurs. The methodology of the study was based on the primary data collected through direct interviews with women entrepreneurs by using an interview schedule with structured questionnaire and an attitude scale. The result points to a poor level of perceptions of identity and poor self-images of women entrepreneurs. The item analysis shows that women entrepreneurs have been very vocal regarding the lack of opportunities vis-à-vis their male counterparts to be successful in their business endeavour. The study also shows that educational level, training status, business-phase, income level and financial management level have caused significant influences on the levels of perception of identity of women entrepreneurs