Issa Rae is not only the co-creator of Insecure [1] but she acts as the lead character in the hit HBO show. In case you need a little refresher, the show centres around Issa's life as she deals with finding love, figuring out her career, and dealing with friendships in Los Angeles. With the start of season four, we decided to take a look back at Issa's style [2] evolution throughout the show. Overall, Issa's wardrobe on the show 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, not only does Issa's character mature, but her style does as well. For season three, Issa tapped former fashion editor Shiona Turini [3] to join the show as a costume designer after working with her on a shoot for a magazine cover. As Issa's character develops, you'll also notice a few changes with her wardrobe choices. Since Shiona joined the show, we've seen Issa's character wear a mix of vintage pieces with elevated ones from designers like Monse, Isabel Marant, and Acne Studios. Keep reading to see some of Issa's best style moments throughout Insecure ahead.
Season 4
Opting for a forest green jacket.
Season 4
Styling a red cutout blazer with jeans.
Season 4
Wearing a checkered turtleneck with an orange skirt.
Season 4
Styling a printed blue sweater with jeans.
Season 4
Wearing a yellow striped Glemaud set.
Season 4
Wearing a yellow sports bra and biker short set with a colorblock jacket.
Season 4
For Halloween [5], Issa dressed up as Jigaboos from Spike Lee's School Daze.
Season 4
Wearing a plaid dress by Ganni.
Season 4
Styling a casual sweatshirt with a checkered skirt.
Season 4
Wearing an orange Nanushka set.
Season 3
Wearing a striped jacket and a printed dress.
Season 3
Pairing an Acne Studios polo with a striped skirt by Silvia Tcherassi.
Season 3
Styling an orange crop top by A.L.C. with a floral miniskirt.
Season 3
Styling a cropped sweater by Monse with high-waisted jeans.
Season 3
Wearing a yellow Out From Under tee with a graphic-print Dries Van Noten blazer.
Season 3
Wearing a Lauryn Hill T-shirt by Melody Ehsani.
Season 3
Wearing a denim bustier by Guess with a Stella Jean miniskirt.
Season 3
Wearing a LyfestyleNYC Biggie Smalls sweatshirt over a Stella Jean shirt.
Season 3
Styling a black turtleneck with beige zip-up pants.
Season 2
Wearing a red sweatshirt by Omondi.
Season 2
Wearing a patterned Maki Oh dress.
Season 2
Wearing a retro D.A.R.E. T-shirt with an acid-washed denim jacket.
Season 2
Wearing an Isabel Marant bomber jacket.
Season 2
Wearing a green trench coat with a brown bag.
Season 2
Styling a puff-sleeve top with acid-wash jeans.
Season 2
Styling a crop top with a printed midi skirt.
Season 2
Wearing a "Wrecked" shirt with jeans.
Season 2
Styling a "The Last Poets" sweatshirt with an orange skirt.
Season 2
Wearing a "We Got Y'all" sweatshirt with jeans and statement earrings.
Season 2
Wearing a black and white cut-out dress.
Season 1
Styling a printed skirt with a denim jacket.
Season 1
Wearing a sporty jacket with a ribbed sweater dress.
Season 1
Wearing a leopard- and zebra-print sweatshirt.
Season 1
Styling a long denim jacket with jeans and red sneakers.
Season 1
Wearing a black graphic-print tee with birds on it.
Season 1
Styling a "We Got Y'all" shirt with a graphic-print blazer.