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Issa Rae's Best Outfits on Insecure

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

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.

Image Source: HBO

Season 4

Opting for a forest green jacket.

Image Source: HBO

Season 4

Styling a red cutout blazer with jeans.

Image Source: HBO

Season 4

Wearing a checkered turtleneck with an orange skirt.

Image Source: HBO

Season 4

Styling a printed blue sweater with jeans.

Image Source: HBO

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Season 4

Wearing a yellow striped Glemaud set.

Image Source: HBO

Season 4

Wearing a yellow sports bra and biker short set with a colorblock jacket.

Image Source: HBO

Season 4

For Halloween, Issa dressed up as Jigaboos from Spike Lee's School Daze.

Image Source: HBO

Season 4

Wearing a plaid dress by Ganni.

Image Source: HBO

Season 4

Styling a casual sweatshirt with a checkered skirt.

Image Source: HBO

Season 4

Wearing an orange Nanushka set.

Image Source: HBO

Season 3

Wearing a striped jacket and a printed dress.

Image Source: HBO

Season 3

Pairing an Acne Studios polo with a striped skirt by Silvia Tcherassi.

Image Source: HBO

Season 3

Styling an orange crop top by A.L.C. with a floral miniskirt.

Image Source: HBO

Season 3

Styling a cropped sweater by Monse with high-waisted jeans.

Image Source: HBO

Season 3

Wearing a yellow Out From Under tee with a graphic-print Dries Van Noten blazer.

Image Source: HBO

Season 3

Wearing a Lauryn Hill T-shirt by Melody Ehsani.

Image Source: HBO

Season 3

Wearing a denim bustier by Guess with a Stella Jean miniskirt.

Image Source: HBO

Season 3

Wearing a LyfestyleNYC Biggie Smalls sweatshirt over a Stella Jean shirt.

Image Source: HBO

Season 3

Styling a black turtleneck with beige zip-up pants.

Image Source: HBO

Season 2

Wearing a red sweatshirt by Omondi.

Image Source: HBO

Season 2

Wearing a patterned Maki Oh dress.

Image Source: HBO

Season 2

Wearing a retro D.A.R.E. T-shirt with an acid-washed denim jacket.

Image Source: HBO

Season 2

Wearing an Isabel Marant bomber jacket.

Image Source: HBO

Season 2

Wearing a green trench coat with a brown bag.

Image Source: HBO

Season 2

Styling a puff-sleeve top with acid-wash jeans.

Image Source: HBO

Season 2

Styling a crop top with a printed midi skirt.

Image Source: HBO

Season 2

Wearing a "Wrecked" shirt with jeans.

Image Source: HBO

Season 2

Styling a "The Last Poets" sweatshirt with an orange skirt.

Image Source: HBO

Season 2

Wearing a "We Got Y'all" sweatshirt with jeans and statement earrings.

Image Source: HBO

Season 2

Wearing a black and white cut-out dress.

Image Source: HBO

Season 1

Styling a printed skirt with a denim jacket.

Image Source: HBO

Season 1

Wearing a sporty jacket with a ribbed sweater dress.

Image Source: HBO

Season 1

Wearing a leopard- and zebra-print sweatshirt.

Image Source: HBO

Season 1

Styling a long denim jacket with jeans and red sneakers.

Image Source: HBO

Season 1

Wearing a black graphic-print tee with birds on it.

Image Source: HBO

Season 1

Styling a "We Got Y'all" shirt with a graphic-print blazer.

Image Source: HBO

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