Although the Belt-Road initiative (BRI), as a ‘model’ government initiative, has attracted great attention from both academia and industry, one central question related to the location choice of Chinese investment remains under-researched. Our study is motivated to reveal how institutional configurations of BRI participant countries that lead to a high volume of Chinese outward investment vary with the BRI. Utilizing the varieties of institutional systems (VIS) framework, we compare two Waves (2008–2013 and 2014–2019) of Chinese outward investment flows into 120 BRI participant countries. Using institutional elements—the roles of the state, financial markets, human capital, social trust, and corporate governance—as a holistic lens, some intriguing findings of patterned Chinese outward investment are observed. Instead of a single best form of institutional environment, various combinations of institutional arrangements are equally effective, but they differ subtly before and after the BRI in attracting Chinese outward investment. Four prototypes of institutional configurations of BRI participant countries are identified, including configurations with compatible institutional settings, institutional voids, ‘idealistic’ VIS conditions, and emerging institutional elements. Corresponding propositions are proposed for future theoretical advancement.