This ethnographic study investigates a distinct Islamic tradition of a Turkish Sufi society, named Rifaiyye, which confronts many conventional Islamic norms on gender. The Rifais, led by an unveiled female sheikh, named Cemalnur Sargut, are marked by their upper middle class, educated, professional and cosmopolitan social profile. They intellectualize Sufism in particular ways that are conducive to their modern pious subjectivities, which finds little resemblance in other modern-pious Islamic movements. They reconfigure the discourses and practices of Islam and modernity in novel ways with particular implications for gender norms. Their disruption of normative Islamic gender discourse involves discarding bodily modesty codes, such as veiling and gender segregation, and extending women’s public participation to the level of community and spiritual leadership. By contextualizing the Rifais in their socio-historical trajectory from the fall of the Ottoman Empire, through the early years of Turkish Republic to the contemporary Turkey, this paper traces their evolving engagement with the dynamic and contested discourses of modernity, secularism, neoliberalism and Islam in Turkey, with its specific ramifications for the status of women. Kenan Rifai (1867-1950), the founder of the Rifaiyye, was an unconventional Sufi sheikh. He was educated in French and worked as a civil bureaucrat in national education sector. His diverse circle included Ottoman ulamas, Sheikhul-Islams, philosophers, Orthodox priests as well as Republican elites among others. He welcomed the Republican reform banning the Sufi lodges in 1925 as the will of God on the basis of their degeneration and incompatibility with modern society’s needs. His Sufi ethos was based on love and ethics aimed at disciplining selves into socially responsible moral agents. Mystical union with God was epitomized not in asceticism, but through active civic participation driven by love. Since love was deemed to be the most powerful tool to cultivate Sufi subjectivity, women were exalted for their greater capacity to love. Most of his prominent students were educated women, one of which (Samiha Ayverdi, 1905-1993) inherited the leadership. Between the 60s and the 90s, Ayverdi established several civil society associations that aimed to preserve the Turkish cultural heritage. Having been operating in a relatively more liberal Turkish civil society in which public Islam has been rendered visible, her successor Cemalnur Sargut has foregrounded the Sufi identity of the group openly. She has initiated academic enterprises on Sufism by endowing university chairs in the US, China, Japan and Turkey as well as organizing international academic conferences.