(Photo by Dave Benett/Getty Images) Issa Rae at Off-White RTW Spring 2025 as part of New York Ready to Wear Fashion Week held at the Brooklyn Bridge Park on September 8, 2024 in New York ...

Watching Issa Rae’s style evolution has been awe-inspiring. Over the course of her career the award-winning actress and serial entrepreneur has transitioned from a fashion newbie to a ...