Issa Rae Is the Queen of Casual Style on Insecure, and These Outfits Prove It

Season 4

From the moment I started watching Insecure, I was drawn not only to the relatable characters, but I also found myself patiently waiting to see what Issa Rae would wear on each episode. She’s the co-creator and the lead of the of the hit HBO show, and in case you need a little refresher (or you’re not watching yet — and, which case, what are you waiting for?!), the show centers around Issa’s life as she navigates love, career, and friendship in LA.

With the fifth and final season slated to premiere on HBO on Oct. 24, we’re looking back at Issa’s onscreen style evolution. Overall, Issa’s wardrobe is full of pieces that feature bold prints and colorful patterns. There are also a ton of vintage pieces, like old Levi’s acid-washed jeans, printed blazers, and political tees.

As the seasons progress, we watch Issa handle her job and career goals, navigate friend drama, and figure out her romantic life. She grows up, and her style matures right along with her. For season three, Issa tapped stylist, consultant, and fashion industry pro, Shiona Turini to join the show as a costume designer after working with her on a magazine shoot. Since Shiona joined the show, we’ve seen Issa’s character wear a mix of vintage pieces with contemporary labels like Monse, Isabel Marant, and Acne Studios. It’s a style evolution that has us anxiously awaiting season five. Until then, keep reading to revisit some of Issa’s best style moments throughout Insecure ahead.

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