Issa Rae has become a natural hair icon of our generation.
And while Insecure's final season has come and gone, I am all for nostalgically noting the many times Issa Rae's hair philosophy lent itself to her character as an homage to the show's cultural impact. As the multi-hyphenate says, "there’s just nothing like seeing a Black woman who switches her hair like the days of the week." That goes double for Issa Dee.
Read our inaugural cover story on Issa's natural hair journey and see below for the Issa hair transformations that will give you natural hair inspo for days. Preesh, Insecure.
The Tried & True TWA
HBO
Classic and understated Issa Dee. In season one, the character was known to rock her TWA (teeny weeny afro) more than anything and seldom switched her hairstyle up from episode to episode.
Blown Out Afro Puff
HBO
This traditional afro puff is a classic amongst natural hair girls everywhere. And Issa rocking it in this season one episode served as a great reminder as to why.
Changes in the way she wore her hair started being more apparent in the series' second season. Instead of just a scarf here or a hair tie there, Issa experimented with twists, braids, and adding length in her hairstyles throughout the seasons moving forward.
Sis switched it up and switched it up often, which was a slight nod to the character's growth.
Half Up Half Down
HBO
This half-up half-down style with a side bang is the definition of ease without sacrificing any chic.
Flat Twisted Pony With A Bang
Justina Mintz/HBO
A bang is a must in this protective style. Flat twisted at the sides, Issa's hair is pulled into a low ponytail and left out in an afro puff. Mirroring that puff is her bang in the front. The end result is balanced and giving protective style inspo for days.
Flat Twisted Bun
Merie W. Wallace/HBO
For this simple protective style, mini flat twists are created and pulled into a low bun with extensions added to give a bun effect.
The evolution of Issa Dee's hair from a simple TWA to more complex, "elevated" hairstyles was a journey stylist Felicia Leatherwood was intentional about portraying.
In reference to season 4's progression, Leatherwood told NYLON, "This last season, I wanted to make sure that it was an upgrade for Issa Dee, which means that I go talk to the wardrobe and makeup and see what direction they're going in."
Elevated Faux Hawk Updo
Merie W. Wallace/HBO
In the premiere of season 4, Issa's coif was polished in a faux hawk updo. While most of the audience was questioning if they should break up with their "Molly," we were pondering how to add this style to our must-try list.
Slick Down Low Afro Puff Ponytail
Merie W. Wallace/HBO
In the second episode of season 4, Issa wore two variations of the slick down puff ponytail style. This iteration is pulled low instead of up and also features accents by way of gold bobby pins.
Merie W. Wallace/HBO
Flat Twisted Ponytail
Merie W. Wallace/HBO
Jumbo flat twists twisted back into a low ponytail with some hair added is how this easy style is achieved. Leatherwood mentioned about the ease of some of Issa's styles on the show, "I really like to represent the natural hair community well, and that's my first step. How can I make this something that's reasonable for any naturalista to recreate? [That they] can look and say, 'Oh, I could do that,' or to see themselves with that hairstyle in their own natural texture and their own flavor."
Low Ponytail With Mini Braids
Merie W. Wallace/HBO
The classic low ponytail style got an update with the addition of two mini braids placed in the front.
Twisted Curly Updo
Merie W. Wallace/HBO
The curly updo is given a bit of additional flair with the help of four perfectly laid flat twists bringing the style together.
Two Buns Accented With Beaded Braids
Merie W. Wallace/HBO
There's no denying Issa loves her updos. In this particular look, Issa adds two beaded braids on each side, going in the opposite direction of her two buns.
Braided Bun Updo With Curly Bang
Raymond Liu/HBO
In the season five opener, Issa experienced a bout of self-doubt while revisiting her alma mater. But one thing's for certain and two thing's for sure, the braided bun updo with the curly bang was the star of the show.
Two Feed-In Braids
Glen Wilson/HBO
The unveiling of this feed-in braid style gave me the summer vibes my life currently needs.
Two Twists In The Front, Hair Out In The Back
Glen Wilson/HBO
This hairstyle is perfection and feels like an update to the classic half up half down ponytail styles. Instead, the front of Issa's hair is sectioned into two and then twisted to meet in the back, with the rest of her hair left out.
Braids In The Front, Ponytail In The Back
Merie Wallace/HBO
Forever in love with the way that a lot of Issa's styles are hybrids and seem to create the perfect style. This style from the current and final season features braids in the front pulled into an exaggerated braided pony in the back.
Featured image by Merie Wallace/HBO
Originally published December 13, 2021
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The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak