Issa Rae’s Iconic Hairstyles: A Natural Hair Journey

Issa Rae’s Hairstyles: Black Hair Culture & Step-by-Step Guide

 Issa Rae dancing joyfully in the mirror on Insecure, celebrating her confidence and free-spirited energy.

The TWA Era - 2015

Issa Rae rocking a TWA (Tiny Weeny Afro)

Natural, radiant, and rocking a short tiny weeny afro, or as we like to call it a TWA. This was around the time Insecure got picked up by HBO and her whole life started to shift. She was stepping further into her purpose, and her crown was right there with her.

Now, this was also the era when the natural hair cult - I mean community - took back permanent residence in the black hair space. Oh what a time it was. We were blending avocado hair masques in out kitchens, using Cantu with the same level of faith we once reserved for Blue Magic grease. Iykyk! This 'get-up-and-go' fro was such a mood. I found myself loving the confidence this phase brings after 4 big chops myself.

This style is low maintenance and has a quick clean up time. This style can be archived using your favorite leave in conditioner, some water and a sponge. You can also just use your hand in a circular motion to bring out the natural texture. This Issa? Oh she meant business, like get out the way I am about to take over HBO business.

The "I Made It" Sleek Braid - 2019

Issa Rae with a simple, yet classy braid remix style

Okayyy—this next look is from 2019, when Issa Rae accepted the inaugural Emerging Entrepreneur Award at the Women in Film Gala. And listen… this moment was on every self-made business owner highlight reel the next day. "I did that ish by myself" was everywhere! Folks were quoting her speech while still asking their grandma to pay for that monthly website subscription

Now this style right here? It pairs perfectly with her 'I made it' power suit. It’s clean, it’s elevated, it’s giving CEO, and like most of Issa’s looks—it’s a quick one-two style. This one takes about an hour to pull together, and here’s what you’ll need:

• Braiding hair (in your desired color)

• A good gel to slick everything down or freeze spray if you’re using a little heat

• A blow dryer

• Needle and thread or pins to secure the braid

Let’s pause for a quick hair PSA, okay? Styles like this can be achieved in multiple ways, and your method should reflect your hair goals. If you’re avoiding heat beyond a blow-dry, stick to gel for hold. But if you’re open to a light press or flat iron, the freeze spray method works great.

Once your hair is slicked back and laid, you’re gonna pre-braid your braiding hair. Then, using either thread or pins, you attach the braid to your base—secure it in, gently distress the braid for texture, and boom. You’re ready.

This look is versatile, elegant, and super remixable. In fact, it’s my go-to style when I’m working with models on the runway. Low effort, high impact, and you can dress it up or down depending on the vibe.

SXSW Marley Hair Triple Section Bun Ponytail - 2025

Issa Rae with a Marley Hair Combo

Now this look builds off the same base as the last segment, with a little twist. This time, instead of braiding hair, you’re gonna want Marley hair to give that textured, natural look. Two packs in the color of your choice should do the trick.

After you slick your hair into three sections—front, middle, and back—you’re going to attach a Marley hair bun to both the front and middle sections. The back section? Leave it out in a ponytail for that extra drama.

Now the time it took me to write this blog was way longer than the time Issa gave her stylist to create a style. Huge shoutout to the stylist because they created time efficient styles that expressed boldness, class, triumph, power, and elegance.

I’d like to thank God in advance for the opportunity to work with the incredibly talented Issa Rae one day in the future. But until then, I’ll be over here typing, styling, and repping Nezy Hair.

Next Up? Chloe and Halle!