•This study uses complexity theory and configurational analysis to explain online shopping behavior.•Online shopping experience and online shopping motivations combine to predict high purchase intention.•Price sensitivity and promotion sensitivity are the most important motivations.•Personalized e-shopping may be successful even when quality of personalization is low. The present study aims to examine purchase behavior in personalized online shopping by employing complexity theory, based on customers’ online shopping experience and online shopping motivations. To address its objectives, a conceptual model is proposed along with research propositions. The research propositions are validated through a survey on 401 customers’ experience with online shopping, by using the data analysis tool fsQCA (fuzzy-set Qualitative Comparative Analysis). The results, indicate nine configurations of online shopping experience and online shopping motivations that lead to high purchase intentions. This study takes a step further the literature of online shopping and the theoretical ground of how customers’ online shopping experience combines with their online shopping motivations in order to predict and explain increased intention to purchase. The findings offer implications for both researchers and online retailers, regarding the development of new theories in personalized e-commerce and the provision of personalized services.