A Look At The Many Hairstyles of Issa Rae's 'Insecure' Character Issa Dee

It’s hard to believe that HBO’s Insecure is gone forever. It was just yesterday that we were being introduced to the storylines and characters of the show that immediately captured our attention and hearts. Now, just like that…Insecure will be a memory of inspirational reruns. If the show did nothing else, it equipped its audience with loads of motivation in the life (what to do and what not to do), fashion, and most definitely the beauty department. Fans looked forward to this show not just for entertainment, but for an overall hip perspective of Black culture which included groovy music, cool eateries, graphic t-shirts (that celebrated being black), and natural hairstyles that gave us curly girls all the feels. When it came to hairdo’s, Issa Rae’s character Issa Dee wasn’t too big on blowouts or silk pressed hair. Her swag consisted of creative twist-outs, braid-updos, curly fros, and we loved her for that. According to the her hairstylist for the show, Felicia Leatherwood, the hairdos that we fell in love with on Dee were decided upon the day of the show. “I do not plan these styles, you guys. They literally are kind of like a creation between Issa and I in the morning,” stated Leatherwood. In honor of the series finale of Insecure, we decided to revisit some of Dee’s hairstyles that gave us major natural hair inspiration. Check out 10 of our favorite looks from season 5.

1. Twist-out

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A twist-out is always appropriate when it comes to natural hair.  Issa’s twist-outs were always well-moisturized and perfectly in place.  

2. Braids

Braids were some of Issa’s best hairdos. These protective styles really matched her vibe and gave her a simple, yet sassy look.   

3. Textured Ponytail

A textured ponytail always worked on Issa. The slick back look allowed us to see all of Issa’s beautiful facial features while the big ponytail elevated the look. 

4. Braids and Ponytail

Cute and simple hairstyles like this on Issa were perfect. You can never go wrong with simple braids and a wash-n-go ponytail. 

5. Big Hair

Big hair always wins, and Issa slayed this look.  

6. French Braids

These two thick braids were the perfect go-to look for Issa.  

7. Top Knot and Braids

Issa gave us all the vintage vibes with this top knot accompanied by bead-adorned braids on the side. 

8. Up-do and Braids

Up-do’s absolutely worked on Issa, and of course the parts and braids made this look pop.

9. Loose Braid and Ponytail

This style has inspiration written all over it. A loose braid that served as a pompadour and a curly ponytail in the back look like this can be worn for several occasions.  

10. Crown Braid

Why wouldn’t the queen sport a crown braid? There are many ways to rock this creative hairstyle, and we love how Issa’s braid was positioned high.