A Closer Look at Issa Rae’s Remarkable Style Evolution

Issa’s fashion journey has been quite captivating. The award-winning actress and entrepreneur, in question, seems to have taken quite a leap from being a fashion novice to being regarded as a true style icon. She still stole the hearts of her followers with that groundbreaking role of hers in Insecure, but what was even more magical, exciting was seeing the evolution of her style. Rap had so many loves for colorful separates way back in the day-of course, they were probably just a tad overly saturated with bold hues and perky patterns.

As time moved on, neither her personal stylist, designer, and official stylist, Jason Rembert, could inspire her latest red carpet moments. Rembert helped make Issa’s looks reach the level of remarkable statements. Most particularly, when she hosted the CFDA Awards in 2018, Rae used the medium to send a powerful message through her bold wearing of only Black designers. Whether it was a striking lime green Sergio Hudson suit or a glittery royal blue Pyer Moss gown, together, such outfits represented the targets shared by the duo in making the change impactfully.

Her style started to take roots more in the hands of stylist Shameelah Hicks Senat and fashion director Wouri Vice. Both managed to encourage out-of-this-world red carpet moments for Issa. Adopting vibrant colors always keeps Rae’s style signature, but now she’s been ultimately choosing eloquent and sequined black gowns for public appearances. The most recent were the opulent AMI Paris gown she wore at the 2024 Academy Awards and a sleek creation made by Valdrin Sahiti for the Vanity Fair after-party, both styled by Vice. She also styled her in the iconic golden Pamela Roland gown for the Golden Globe Awards last year.

One of Issa’s most memorable fashion moments was the Barbie movie sequel 2023. At one of these functions, she sparkled in a kelly-green feathered vintage gown by PatBO, and as for the world preview, she slipped into a little custom magenta Marc Bouwer. Both look into the creativity and confidence of Issa in her fashion choices.

We see that her current outfits promote a further transformation of her style. And while sequins and some classic black and gold tones may be regarded as safe choices by others, Issa has in a way made them her signature wear. Felician Leatherwood, her longtime hairdresser, develops how this is achieved through makeup artist Joanna Shimkin and her esteemed stylist. They brought life to the peculiar stylistic universe of Issa through her public appearance.

To celebrate Issa Rae’s birthday, let’s take a look back at some of her most iconic fashion moments-past and present-which have helped solidify her reputation as a fashionista in Hollywood.