Popsugar Fashion Black Women Issa Rae's Best Outfits on Insecure Issa Rae Is the Queen of Casual Style on Insecure and These Outfits Prove It 14 April 2020 by Nikita Charuza Image Source: HBO Issa Rae is not only the co-creator of Insecure 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 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 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. Related: Issa Rae's Stunning Engagement Ring Is Truly Hard to Miss — It's THAT Beautiful Season 4 Image Source: HBO Opting for a forest green jacket. 1 / 36 Season 4 Image Source: HBO Styling a red cutout blazer with jeans. 2 / 36 Season 4 Image Source: HBO Wearing a checkered turtleneck with an orange skirt. 3 / 36 Season 4 Image Source: HBO Styling a printed blue sweater with jeans. 4 / 36 Season 4 Image Source: HBO Wearing a yellow striped Glemaud set. 5 / 36 Season 4 Image Source: HBO Wearing a yellow sports bra and biker short set with a colorblock jacket. 6 / 36 Season 4 Image Source: HBO For Halloween, Issa dressed up as Jigaboos from Spike Lee's School Daze. 7 / 36 Season 4 Image Source: HBO Wearing a plaid dress by Ganni. 8 / 36 Season 4 Image Source: HBO Styling a casual sweatshirt with a checkered skirt. 9 / 36 Season 4 Image Source: HBO Wearing an orange Nanushka set. 10 / 36 Season 3 Image Source: HBO Wearing a striped jacket and a printed dress. 11 / 36 Season 3 Image Source: HBO Pairing an Acne Studios polo with a striped skirt by Silvia Tcherassi. 12 / 36 Season 3 Image Source: HBO Styling an orange crop top by A.L.C. with a floral miniskirt. 13 / 36 Season 3 Image Source: HBO Styling a cropped sweater by Monse with high-waisted jeans. 14 / 36 Season 3 Image Source: HBO Wearing a yellow Out From Under tee with a graphic-print Dries Van Noten blazer. 15 / 36 Season 3 Image Source: HBO Wearing a Lauryn Hill T-shirt by Melody Ehsani. 16 / 36 Season 3 Image Source: HBO Wearing a denim bustier by Guess with a Stella Jean miniskirt. 17 / 36 Season 3 Image Source: HBO Wearing a LyfestyleNYC Biggie Smalls sweatshirt over a Stella Jean shirt. 18 / 36 Season 3 Image Source: HBO Styling a black turtleneck with beige zip-up pants. 19 / 36 Season 2 Image Source: HBO Wearing a red sweatshirt by Omondi. 20 / 36 Season 2 Image Source: HBO Wearing a patterned Maki Oh dress. 21 / 36 Season 2 Image Source: HBO Wearing a retro D.A.R.E. T-shirt with an acid-washed denim jacket. 22 / 36 Season 2 Image Source: HBO Wearing an Isabel Marant bomber jacket. 23 / 36 Season 2 Image Source: HBO Wearing a green trench coat with a brown bag. 24 / 36 Season 2 Image Source: HBO Styling a puff-sleeve top with acid-wash jeans. 25 / 36 Season 2 Image Source: HBO Styling a crop top with a printed midi skirt. 26 / 36 Season 2 Image Source: HBO Wearing a "Wrecked" shirt with jeans. 27 / 36 Season 2 Image Source: HBO Styling a "The Last Poets" sweatshirt with an orange skirt. 28 / 36 Season 2 Image Source: HBO Wearing a "We Got Y'all" sweatshirt with jeans and statement earrings. 29 / 36 Season 2 Image Source: HBO Wearing a black and white cut-out dress. 30 / 36 Season 1 Image Source: HBO Styling a printed skirt with a denim jacket. 31 / 36 Season 1 Image Source: HBO Wearing a sporty jacket with a ribbed sweater dress. 32 / 36 Season 1 Image Source: HBO Wearing a leopard- and zebra-print sweatshirt. 33 / 36 Season 1 Image Source: HBO Styling a long denim jacket with jeans and red sneakers. 34 / 36 Season 1 Image Source: HBO Wearing a black graphic-print tee with birds on it. 35 / 36 Season 1 Image Source: HBO Styling a "We Got Y'all" shirt with a graphic-print blazer. 36 / 36 Black WomenWomen Of ColorInsecureIssa RaeScreen StyleTVAcne StudiosA.L.C.MonseDries Van Noten