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Since bursting on the scene with the cultural-favorite show “Insecure” seven years ago, Issa Rae has quickly taken Hollywood and the world by storm. Apart from being one of the entertainment industry’s most innovative writers and actors, Rae has made quite the sartorial mark. She initially cemented herself as the queen of elevated casual style on her hit show, but she’s also becoming one to watch when it comes to red carpet fashion. From nearly breaking the internet with a custom Vera Wang Haute dress at her wedding to husband Louis Diame to fearlessly dominating the 2021 Emmy Awards with a sheer Aliétte dress and grillz, the actress’s looks are guaranteed to be a hit.

Although she’s an undeniable force on her own, we have celebrity stylist Jason Rembert to thank for collaborating on Rae’s style evolution. The two connected when Rae’s publicist offered him the job at one of his “Insecure” premiere parties, and they’ve produced nothing but noteworthy looks ever since. “I create looks to be elevated, comfortable, while still being true to who she is,” Rembert told Harper’s Bazaar in 2020.

While Rae’s days as the YouTuber behind “Awkward Black Girl” were often defined by leather jackets and combat boots, the 38-year-old has since graduated to statement-making silhouettes and sleek heels, even nailing some of the biggest red carpet trends, including plunging necklines and naked dresses. Rae really began commanding attention at the 2018 Golden Globe Awards, wearing a shimmery, black gown complete with a cape and thigh-high slit by Prabal Gurung. She also nailed cutouts at the 2022 Emmy Awards, wearing a custom Sergio Hudson dress that showed off her toned stomach.

The “Rap Sh!t” producer’s style has been centerstage as she makes the rounds promoting the “Barbie” movie and her role as President Barbie. This time styled by Wouri Vice, she’s been championing the Barbiecore trend with dresses like her Marc Bouwer pink velvet, boob-window gown. The actress also took things up a notch at the VIP Photocall in London, wearing a multicolored, A-line minidress with a green feathered hem from PatBO, further diversifying the image of the iconic American doll.

Recently, she stepped out for a Shipt event in New York City in the perfect dress. Her look featured a micro-mini hem, elevated by a fringe skirt that fell to her ankles. She brought the look together with strappy sandals and box braids styled in a high ponytail. At the event, Rae revealed that she teamed up with Shipt’s CMO Alia Kemet to mentor four Howard University students, who filmed, edited, and starred in a national ad campaign for the brand’s new student membership program. “This does not happen,” Rae told students Avery Harrell, Serenity Owens, and Gavin Kelley, and Kayla Collins. “Corporations will give a lot of lip service sometimes, and the fact that you are now able to create something great that is airing in Times Square every 30 seconds with your beautiful faces and your beautiful work – this can go on your résumé forever.”

Keep scrolling to see Issa Rae’s latest look, as well as her best fashion moments throughout the years.