Issa Rae’s Hairstyles In Insecure Season 4 Have A Story To Tell

If you caught the season 4 premiere of HBO's hit series Insecure on Sunday night, you probably picked up on one of its biggest themes: self-care. The episode takes place two years after we last saw Issa Dee (Issa Rae), and kicks off with the main character meeting up with her best friend Molly Carter (Yvonne Orji) for a leisurely Sunday of yoga and recreational cannabis (which is legal in Los Angeles, where the show is set).

The self-care narrative isn't all that caught our attention: Issa's hairstyles also stole the show, with a variety of looks that we're now learning have everything to do with her path of personal discovery and growth. "She's maturing and taking more control of her life and look," says Felicia Leatherwood, Issa Rae's longtime hairstylist, who works with the actress on the show and IRL. "In this new season, you'll see the reflection of every season come into the fold. You see her becoming more independent, and the hair reflects that."

Issa might be evolving, but her wide array of hairstyles isn't going anywhere. As we've seen from season to season, her hairstyles always suit her day-to-day activities, whether it's a sleek braided updo for work or a faux-hawk for Coachella. The variety, Leatherwood explains, isn't just a reflection of Issa, but of Black women everywhere — which is why it's so important to portray caring for her hair accurately, too.

"If you watch anything that Issa's done [in her career], she keeps it real," says Leatherwood. "As women of colour, we change our hair all the time and wrap it up at night, so it only makes sense she does. Every time we do Insecure, it's always a moment for us to showcase a Black woman that's going to change her hair from day to day, sometimes moments in which her life is changing."

The attention to detail makes Leatherwood proud of the significance of Issa's hairstyles onscreen. "We're showing the world that natural hair is not strange — there's nothing abnormal about it," the hair pro tells us. "For me, it's about representing the natural hair community well, and giving them options."

That's why you'll find so many hair changes throughout the series, as we already saw in the trailer for season four, with a different hairstyle in all of Issa Dee's appearances within the two-minute clip.

"At the top of my list is that the hairstyles are ones that another woman could recreate if she wants," says Leatherwood. As she plans the hairstyles ahead of time — which requires reading the script and then meeting with the wardrobe team — she also takes into consideration how difficult it'd be for viewers to recreate, along with whether the look would actually be worn by Issa Rae IRL. "I always check in to make sure she's comfortable with the style, and that it makes sense to her. "

While Leatherwood couldn't give us details on the rest of the season, she did tell us that we can expect the inclusion of more hairpieces in the upcoming episodes. But what she's most excited about is for everyone to see the scenes in which these hairstyles come to life. "I liked [the hairstyles] more because of the scene that was being played out with them," she says. 

Issa's hairstyles aren't the only thing that's accessible: The products Leatherwood reaches for behind the scenes are, too. She's a fan of under-$25 favourites like Curls Blueberry Bliss Reparative Leave In Conditioner, which works to condition overworked curls, and Obia Naturals Curl Enhancing Custard, which Leatherwood says is a great choice for texture 4 hair. She also recommends her own detangling brush for anyone who wants to recreate the looks. "I created that brush for hair types like textured, coarse, or coily to detangle the hair without ripping it out," she says. "I use that brush wet or dry. If I want to give Issa more of an Afro, I use the brush dry to give the hair more volume; if I wanted to give her hair more definition, I'd use it wet."

And while viewers are at it, Leatherwood urges them to walk away inspired to play with their natural textures and recreate the looks — even if it's just to stay home and do your own self-care Sunday. She says, "Pause it, replay it. I like for women to be able to see it, feel good, and feel like they can do it themselves."