'Insecure': Issa Dee's 8 Best Hairstyles From Seasons 4 and 5

issa hairstyles insecure
credit: Glen Wilson/HBO

From simple tapered cuts to elaborate braided designs, no matter how questionable her behavior, Issa’s hair is always on-point on Insecure.

This is largely due to Felicia Leatherwood, the genius behind Issa’s cropped, tight ‘do on and off-screen. She takes great care to keep Issa perfectly coiffed and treats her hairstyles like another layer to the character.

Leatherwood explained,

“If [Issa’s] depressed, then I’ve got to create a hairstyle that shows you that she’s unhappy and she didn’t care that day, because these are the moods we go through as women anyway, and so sometimes we may fix ourselves up when we don’t feel good, and other times we may not fix ourselves up when we don’t feel good.”

What’s most refreshing is that Issa proudly displays the versatility of natural hair in a TV landscape that has most black women in some sort of wig. (It’s a bit of a dirty secret amongst naturals that even women with big, bouncing curly afros on TV are wearing some sort of extension).

Issa’s constant stream of natural hair porn gets at the heart of the relationship every black woman has with her hair. As Leatherwood explains,

“Just to keep it real — most sistas know that it doesn’t matter what’s going on in your life. You’re gonna make sure your hair is done! You can be sleeping on someone’s couch, but guess what? You’re gonna look good!”

For Black women, our hair is an important piece of armor and many of us spend entire afternoons ever weekend doing elaborate maintenance routines. For us, perfectly set curls are essential to contending with the ups and downs of a world that has been traditionally hostile to our natural hair. In the same way, Issa may be underemployed, broke, and terrible at relationships, but her hairstyles are always together. Here are some of our favorites:

1. Season 5, Episode 8 ‘Surviving, Okay?!’

iss hairstyles insecure
credit: Merie Wallace/HBO

2. Season 5, Episode 4 ‘Faulty, Okay?!’

insecure issa hairstyles
credit: Merie W. Wallace/HBO

3. Season 4, Episode 6 ‘Lowkey Done’

insecure issa braids
credit: Merie W. Wallace/HBO

4. Season 4, Episode 3 ‘Lowkey Thankful’

issa hairstyles insecure hbo
credit: Merie W. Wallace/HBO

5. Season 5, Episode 10 ‘Everything Gonna Be, Okay?!’

issa hair insecure season 5
credit: Raymond Liu/HBO

6. Season 5, Episode 2 ‘Growth, Okay?!’

issa hairstyles season 5 insecure
credit: Glen Wilson / HBO

7. Season 5, Episode 6 ‘Tired, Okay?!’

issa dee hairstyles insecure
credit: Merie Wallace/HBO

8. Season 4, Episode 2 ‘Lowkey Distant’

issa hairstyles isnecure
credit: Merie W. Wallace/HBO

If you’d like to try out some of these styles yourself, make sure you check out celebrity hairstylist Felicia Leatherwood’s Instagram account for tips. You can also buy some human wigs to give you more opportunities for other hairstyles


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Ayo Osobamiro
Ayo is a writer and producer based in Brooklyn, but proudly from the Midwest. When she's not agonizng over applying to grad school, she is working on her first podcast, I Think I Read This Somewhere