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 colourful 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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Season 1
Styling a “We Got Y’all” shirt with a graphic-print blazer.
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Season 1
Wearing a black graphic-print tee with birds on it.
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Season 1
Styling a long denim jacket with jeans and red sneakers.
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Season 1
Wearing a leopard- and zebra-print sweatshirt.
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Season 1
Wearing a sporty jacket with a ribbed sweater dress.
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Season 1
Styling a printed skirt with a denim jacket.
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Season 2
Wearing a black and white cut-out dress.
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Season 2
Wearing a “We Got Y’all” sweatshirt with jeans and statement earrings.
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Season 2
Styling a “The Last Poets” sweatshirt with an orange skirt.
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Season 2
Wearing a “Wrecked” shirt with jeans.
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Season 2
Styling a crop top with a printed midi skirt.
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Season 2
Styling a puff-sleeve top with acid-wash jeans.
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Season 2
Wearing a green trench coat with a brown bag.
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Season 2
Wearing an Isabel Marant bomber jacket.
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Season 2
Wearing a retro D.A.R.E. T-shirt with an acid-washed denim jacket.
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Season 2
Wearing a patterned Maki Oh dress.
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Season 2
Wearing a red sweatshirt by Omondi.
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Season 3
Styling a black turtleneck with beige zip-up pants.
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Season 3
Wearing a LyfestyleNYC Biggie Smalls sweatshirt over a Stella Jean shirt.
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Season 3
Wearing a denim bustier by Guess with a Stella Jean miniskirt.
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Season 3
Wearing a Lauryn Hill T-shirt by Melody Ehsani.
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Season 3
Wearing a yellow Out From Under tee with a graphic-print Dries Van Noten blazer.
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Season 3
Styling a cropped sweater by Monse with high-waisted jeans.
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Season 3
Styling an orange crop top by A.L.C. with a floral miniskirt.
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Season 3
Pairing an Acne Studios polo with a striped skirt by Silvia Tcherassi.
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Season 3
Wearing a striped jacket and a printed dress.
HBO / Merie Weismiller Wallace - SMPSP
Season 4
Wearing an orange Nanushka set.
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Season 4
Styling a casual sweatshirt with a checkered skirt.
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Season 4
Wearing a plaid dress by Ganni.
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Season 4
For Halloween, Issa dressed up as Jigaboos from Spike Lee’s School Daze.
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Season 4
Wearing a yellow sports bra and biker short set with a colorblock jacket.
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Season 4
Wearing a yellow striped Glemaud set.
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Season 4
Styling a printed blue sweater with jeans.
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Season 4
Wearing a checkered turtleneck with an orange skirt.
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Season 4
Styling a red cutout blazer with jeans.
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Season 4
Opting for a forest green jacket.
