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

Issa Rae's Best Outfits on Insecure

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

Issa Rae's Best Outfits on Insecure
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.

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Season 4

Season 4
Image Source: HBO

Opting for a forest green jacket.

1 / 36

Season 4

Season 4
Image Source: HBO

Styling a red cutout blazer with jeans.

2 / 36

Season 4

Season 4
Image Source: HBO

Wearing a checkered turtleneck with an orange skirt.

3 / 36

Season 4

Season 4
Image Source: HBO

Styling a printed blue sweater with jeans.

4 / 36

Season 4

Season 4
Image Source: HBO

Wearing a yellow striped Glemaud set.

5 / 36

Season 4

Season 4
Image Source: HBO

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

6 / 36

Season 4

Season 4
Image Source: HBO

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

7 / 36

Season 4

Season 4
Image Source: HBO

Wearing a plaid dress by Ganni.

8 / 36

Season 4

Season 4
Image Source: HBO

Styling a casual sweatshirt with a checkered skirt.

9 / 36

Season 4

Season 4
Image Source: HBO

Wearing an orange Nanushka set.

10 / 36

Season 3

Season 3
Image Source: HBO

Wearing a striped jacket and a printed dress.

11 / 36

Season 3

Season 3
Image Source: HBO

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

12 / 36

Season 3

Season 3
Image Source: HBO

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

13 / 36

Season 3

Season 3
Image Source: HBO

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

14 / 36

Season 3

Season 3
Image Source: HBO

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

15 / 36

Season 3

Season 3
Image Source: HBO

Wearing a Lauryn Hill T-shirt by Melody Ehsani.

16 / 36

Season 3

Season 3
Image Source: HBO

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

17 / 36

Season 3

Season 3
Image Source: HBO

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

18 / 36

Season 3

Season 3
Image Source: HBO

Styling a black turtleneck with beige zip-up pants.

19 / 36

Season 2

Season 2
Image Source: HBO

Wearing a red sweatshirt by Omondi.

20 / 36

Season 2

Season 2
Image Source: HBO

Wearing a patterned Maki Oh dress.

21 / 36

Season 2

Season 2
Image Source: HBO

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

22 / 36

Season 2

Season 2
Image Source: HBO

Wearing an Isabel Marant bomber jacket.

23 / 36

Season 2

Season 2
Image Source: HBO

Wearing a green trench coat with a brown bag.

24 / 36

Season 2

Season 2
Image Source: HBO

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

25 / 36

Season 2

Season 2
Image Source: HBO

Styling a crop top with a printed midi skirt.

26 / 36

Season 2

Season 2
Image Source: HBO

Wearing a "Wrecked" shirt with jeans.

27 / 36

Season 2

Season 2
Image Source: HBO

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

28 / 36

Season 2

Season 2
Image Source: HBO

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

29 / 36

Season 2

Season 2
Image Source: HBO

Wearing a black and white cut-out dress.

30 / 36

Season 1

Season 1
Image Source: HBO

Styling a printed skirt with a denim jacket.

31 / 36

Season 1

Season 1
Image Source: HBO

Wearing a sporty jacket with a ribbed sweater dress.

32 / 36

Season 1

Season 1
Image Source: HBO

Wearing a leopard- and zebra-print sweatshirt.

33 / 36

Season 1

Season 1
Image Source: HBO

Styling a long denim jacket with jeans and red sneakers.

34 / 36

Season 1

Season 1
Image Source: HBO

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

35 / 36

Season 1

Season 1
Image Source: HBO

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

36 / 36
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