A Close Look At Issa Rae's Transcendent Style Evolution

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 connoisseur of sorts. While Rae may have captured hearts and garnered fans from the very beginning with Insecure, her journey on the style front has also been enjoyable to witness. Years ago, for appearances, the actress would lean on colorful separates to point to her affinity for bold hues and patterns.

As time stretched on she began working with stylist and designer Jason Rembert who transformed her red carpet looks into full-on moments. Rembert was responsible for the looks she wore while hosting the CFDA Awards in 2018–while hosting she exclusively wore Black designers. For the affair Rembert styled her in a lime green suit by Sergio Hudson and a sparkly blue gown by Pyer Moss. These outfits pointed to Rembert and Rae’s dedication to leaving a longstanding statement.

Stylist Shameelah Hicks Senat is also responsible for moments in Rae’s fashion history. Fashion director and stylist Wouri Vice has also worked with Issa. He’s executed quite a few memorable red carpet moments for the actress. Vibrant hues are still a favorite of Rae’s but for appearances elegant sequined numbers in black have become her go-to. For example, to the Academy Awards in 2024 Issa showed up in a decadent gown by AMI Paris. She switched up her vibe a bit for the Vanity Fair after-party. To attend this affair she donned a gown with succinct detailing by Valdrin Sahiti (both of these looks were styled by Vice). Vice is also responsible for the golden Pamela Roland gown Rae wore to last year’s Golden Globe Awards.

Who can forget Issa’s stylish run that ensued for the 2023 box office hit Barbie? For one Barbie event Wouri Vice dressed her in a kelly green feathered frock by PatBO–for another, the world premiere, she donned a custom Marc Bouwer creation in a magenta hue. 

Rae’s latest looks allude to her steadfastness regarding her fashion transformation. To some sequins and tones like black and gold could be viewed as easy cop-outs. But, to Rae, they are a part of her style universe. With the help of her longtime hairstylist Felicia Leatherwood, her makeup artist Joanna Simkin, and her stylists Issa’s public appearances have become distinctive.

Below take a look at some of Issa Rae’s formative fashion moments from the past and present in celebration of her birthday.