Jason Rembert’s star-studded roster reads like a who’s who of Black Hollywood. The creative infuses a unique edge into luxe garments. Working with burgeoning brands and curating minimalist looks that highlight natural hair and glistening skin as standout accessories, Rembert is one of the most dynamic stylists of his generation. In addition to launching his ultrachic label, Aliétte, he has made his mark in the industry by shaping actress and producer Issa Rae’s aesthetic.

Since Rae’s popular HBO series, Insecure, hit the small screen in 2016, all eyes have been on her. From making red-carpet appearances to hosting the CFDA Awards, she is a force in the sartorial game—and Rembert has been the brains behind her flawless fits. Here he provides a sneak peek at what it’s like to work with Issa Rae.

You don’t have to wear a dress all the time on the red carpet. It’s always important to take risks.”