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
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
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
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
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
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
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
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
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
Amber Riley has the type of laugh that sticks with you long after the raspy, rhythmic sounds have ceased. It punctuates her sentences sometimes, whether she’s giving a chuckle to denote the serious nature of something she just said or throwing her head back in rip-roarious laughter after a joke. She laughs as if she understands the fragility of each minute. She chooses laughter often with the understanding that future joy is not guaranteed.
Credit: Ally Green
The sound of her laughter is rivaled only by her singing voice, an emblem of the past and the future resilience of Black women stretched over a few octaves. On Fox’s Glee, her character Mercedes Jones was portrayed, perhaps unfairly, as the vocal duel to Rachel Berry (Lea Michele), offering rough, full-throated belts behind her co-star’s smooth, pristine vocals. Riley’s always been more than the singer who could deliver a finishing note, though.
Portraying Effie White, she displayed the dynamic emotions of a song such as “And I'm Telling You I'm Not Going” in Dreamgirls on London’s West End without buckling under the historic weight of her predecessors. With her instrument, John Mayer’s “Gravity” became a religious experience, a belted hymnal full of growls and churchy riffs. In her voice, Nicole Scherzinger once said she heard “the power of God.”
Credit: Ally Green
Riley’s voice has been a staple throughout pop culture for nearly 15 years now. Her tone has become so distinguishable that most viewers of Fox’s The Masked Singer recognized the multihyphenate even before it was revealed that she was Harp, the competition-winning, gold-masked figure with an actual harp strapped to her back.
Still, it wasn’t until recently that Riley began to feel like she’d found her voice. This sounds unbelievable. But she’s not referring to the one she uses on stage. She’s referencing the voice that speaks to who she is at her core. “Therapy kind of gave me the training to speak my mind,” the 37-year-old says. “It’s not something we’re taught, especially as Black women. I got so comfortable in [doing so], and I really want other people, especially Black women, to get more comfortable in that space.”
“Therapy kind of gave me the training to speak my mind. It’s not something we’re taught, especially as Black women."
If you ask Riley’s manager, Myisha Brooks, she’ll tell you the foundation of who the multihyphenate is hasn’t changed much since she was a kid growing up in Compton. “She is who she is from when I met her back when she was singing in the front of the church to back when she landed major roles in film and TV,” Brooks says. Time has allowed Riley to grow more comfortable, giving fans a more intimate glimpse into her life, including her mental health journey and the ins and outs of show business.
The actress/singer has been in therapy since 2019, although she suffered from depression and anxiety way before that. In a recent interview with Jason Lee, she recalls having suicidal ideation as a kid. By the time she started seeing a psychologist and taking antidepressants in her thirties, her body had become jittery, a physical reminder of the trauma stacked high inside her. “I was shaking in [my therapist’s] office,” she tells xoNecole. “My fight or flight was on such a high level. I was constantly in survival mode. My heart was beating fast all the time. All I did was sweat.”
There wasn’t just childhood trauma to account for. After auditioning for American Idol and being turned away by producers, Riley began working for Ikea and nearly missed her Glee audition because her car broke down on the highway while en route. Thankfully, Riley had been cast to play Mercedes Jones. American Idol had temporarily convinced her she wasn’t cut out for the entertainment industry, but this was validation that she was right where she belonged. Glee launched in 2009 with the promise of becoming Riley’s big break.
In some ways, it was. The show introduced Riley to millions of fans and catapulted her into major Hollywood circles. But in other ways, it became a reminder of the types of roles Black women, especially those who are plus-sized, are relegated to. Behind the scenes, Riley says she fought for her character "to have a voice" but eventually realized her efforts were useless. "It finally got to a point where I was like, this is not my moment. I'm not who they're choosing, and this is just going to have to be a job for me for now," she says. "And, that's okay because it pays my bills, I still get to be on television, I'm doing more than any other Black plus-sized women that I'm seeing right now on screen."
The actress can recognize now that she was navigating issues associated with trauma and low self-esteem at the time. She now knows that she's long had anxiety and depression and can recognize the ways in which she was triggered by how the cult-like following of the show conflicted with her individual, isolated experiences behind the scenes. But she was in her early '20s back then. She didn't yet have the language or the tools to process how she was feeling.
Riley says she eventually sought out medical intervention. "When you're in Hollywood, and you go to a doctor, they give you pills," she says, sharing a part of her story that she'd never revealed publicly before now. "[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that's not fixing my problem. If anything, it's making it worse."
“[I was] on medication and developing a habit of medicating to numb, not understanding I was developing an addiction to something that’s not fixing my problem. If anything it’s making it worse.”
Credit: Ally Green
At one point, while in her dressing room on set, she rested her arm on a curling iron without realizing it. It wasn't until her makeup artist alerted her that she even realized her skin was burning. Once she noticed, she says she was "so zonked out on pills" that she barely reacted. Speaking today, she holds up her arm and motions towards a scar that remains from the incident. She sought help for her reliance on the pills, but it would still be years before she finally attended therapy.
This stress was only compounded by the trauma of growing up in poverty and the realities of being a "contract worker." "Imagine going from literally one week having to borrow a car to get to set to the next week being on a private jet to New York City," she says. After Glee ended, so did the rides on private planes. The fury of opportunities she expected to follow her appearance on the show failed to materialize. She wasn't even 30 yet, and she was already forced to consider if she'd hit her career peak.
. . .
We’re only four minutes into our Zoom call before Riley delivers her new adage to me. “My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway,” she says.
On this Thursday afternoon in April, the LA-based entertainer is seated inside her closet/dressing room wearing a cerulean blue tank top with matching shorts and eating hot wings. This current phase of healing hinges on balance. It’s about having discipline and consistency, but not at the risk of inflexibility. She was planning to head to the gym, for instance, but she’s still tired from the “exhausting” day before. Instead, she’s spent her day receiving a massage, eating some chicken wings, and planning to spend quality time with friends. “I’m not going to beat myself up for it. I’m not going to talk down to myself. I’m going to eat my chicken wings, and then tomorrow I’m [back] in the gym,” she says.
“My new mantra is ‘humility does not serve me.’ Humility does not serve Black women. The world works so hard to humble us anyway."
This is the balance with which she's been approaching much of her life these days. It's why she's worried less about whether or not people see her as someone who is humble. She'd rather be respected. "I think you should be a person that's easy to work with, but in the moments where I have to ruffle feathers and make waves, I'm not shying away from that anymore. You can do it in love, you don't have to be nasty about it, but I had to finally be comfortable with the fact that setting boundaries around my life – in whatever aspect, whether that's personal or business – people are not going to like it. Some people are not going to have nice things to say about you, and you gotta be okay with it," she says.
When Amber talks about the constant humbling of Black women in Hollywood, I think of the entertainers before her who have suffered from this. The brilliant, consistent, overqualified Black women who have spoken of having to fight for opportunities and fair pay. Aretha Franklin. Viola Davis. Tracee Ellis Ross. There's a long list of stars whose success hasn't mirrored their experiences behind the scenes.
Credit: Ally Green
If Black women outside of Hollywood are struggling to decrease the pay gap, so, too, are their wealthier, more famous peers.
Riley says there’s been progress in recent years, but only in small ways and for a limited group of people. “This business is exhausting. The goalpost is constantly moving, and sometimes it’s unfair,” she says. But, I have to say it’s the love that keeps you going.”
“There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman,” she continues. “We’re still niche. We’re still not main characters.”
"There’s no way you can continue to be in this business and not love it, especially being a plus-sized Black woman. We’re still niche. We’re still not main characters.”
Last year, Riley starred alongside Raven Goodwin in the Lifetime thriller Single Black Female (a modern, diversified take on 1992’s Single White Female). It was more than a leading role for the actress, it also served as proof that someone who looks like her can front a successful project without it hinging on her identity. It showcased that the characters she portrays don’t “have to be about being a big girl. It can just be a regular story.”
Riley sees her work in music as an extension of her efforts to push past the rigid stereotypes in entertainment. Take her appearance on The Masked Singer, for instance. Riley said she decided to perform Mayer’s “Gravity” after being told she couldn’t sing it years earlier. “I wanted to do ‘Gravity’ on Glee. [I] was told no, because that’s not a song that Mercedes would do,” she says. “That was a full circle moment for me, doing that on that show and to hear what it is they had to say.”
As Scherzinger praised the “anointed” performance, a masked Riley began to cry, her chest heaving as she stood on stage, her eyes shielded from view. “You have to understand, I have really big names – casting directors, producers, show creators – that constantly tell me ‘I’m such a big fan. Your talent is unmatched.’ Hire me, then,” she says, reflecting on the moment.
Recently, she’s been in the studio working on original music, the follow-up to her independently-released debut EP, 2020’s Riley. The sequel to songs such as the anthemic “Big Girl Energy” and the reflective ballad “A Moment” on Riley, this new project hones in on the singer’s R&B roots with sensual grooves such as the tentatively titled “All Night.” “You said I wasn’t shit, turns out that I’m the shit. Then you called me a bitch, turns out that I’m that bitch. You said no one would want me, well you should call your homies,” she sings on the tentatively titled “Lately,” a cut about reflecting on a past relationship. From the forthcoming project, xoNecole received five potential tracks. Fans likely already know the strengths and contours of Riley’s vocals, but these new songs are her strongest, most confident offerings as an artist.
“I am so much more comfortable as a writer, and I know who I am as an artist now. I’m evolving as a human being, in general, so I’m way more vulnerable in my music. I’m way more willing to talk about whatever is on my mind. I don’t stop myself from saying what it is I want to say,” she says.
Credit: Ally Green
“Every era and alliteration of Amber, the baseline is ‘Big Girl Energy.’ That’s the name of her company,” her manager Brooks says, referencing the imprint through which Riley releases her music after getting out of a label deal several years ago. “It’s just what she stands for. She’s not just talking about size, it’s in all things. Whether it’s putting your big girl pants on and having to face a boardroom full of executives or sell yourself in front of a casting agent. It’s her trying to achieve the things she wants to do in life.”
Riley says she has big dreams beyond releasing this new music, too. She’d love to star in a rom-com with Winston Duke. She hasn't starred in a biopic yet, but she’d revel in the opportunity to portray Rosetta Tharpe on screen. She’s determined that her previous setbacks won’t stop her from dreaming big.
“I think one of my superpowers is resilience because, at the end of the day, I’m going to kick, scream, cry, cuss, be mad and disappointed, but I’m going to get up and risk having to deal with it all again. It’s worth it for the happy moments,” she says.
If Riley seems more comfortable and confident professionally, it’s because of the work she’s been doing in her personal life.
She’d previously spoken to xoNecole about becoming engaged to a man she discovered in a post on the site, but she called things off last year. For Valentine’s Day, she revealed her new boyfriend publicly. “I decided to post him on Valentine’s Day, partially because I was in the dog house. I got in trouble with him,” she says, half-joking before turning serious. “The breakup was never going to stop me from finding love. Or at least trying. I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness, and you enjoy it and work through it.”
Credit: Ally Green
"I don’t owe anybody a happily ever after. People break up. It happens. When it was good, it was good. When it was bad, it was terrible, hunny. I had to get the fuck up out of there. You find happiness and you enjoy it and work through it.”
With her ex, Riley was pretty outspoken about her relationship, even appearing in content for Netflix with him. This time around is different. She’s not hiding her boyfriend of eight months, but she’s more protective of him, especially because he’s a father and isn’t interested in becoming a public figure.
She’s traveling more, too. It’s a deliberate effort on her part to enjoy her money and reject the trauma she’s developed after experiencing poverty in her childhood. “I live in constant fear of being broke. I don’t think you ever don’t remember that trauma or move past that. Now I travel and I’m like, listen, if it goes, it goes. I’m not saying [to] be reckless, but I deserve to enjoy my hard work.”
After everything she’s been through, she certainly deserves to finally let loose a bit. “I have to have a life to live,” she says. “I’ve got to have a life worth fighting for.”
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We've heard this same song replayed over and over again: Women are stressed and overworked, underpaid, and overlooked in the workplace. Research and everyday experiences back up this claim. And Black women face the added stress of discrimination, even lower pay, and being head of household for a large percentage of homes.
So, how can we get out of survival mode? How can we take deliberate steps to thrive? I'm a huge fan of looking at things from a balanced point of view. I refuse to wear those woe-is-me-it's-hard-being-a-Black-woman tinted glasses often sold to us by propaganda and fear mongers. Here are a few tips that helped me to finally step out of survival mode and into thrive mode:
1. Own your career choices with a mindset shift from lack to optimistic focus and discipline.
It can seem tough to radically approach your career moves as a journey filled with empowering choices, especially when bills have to be paid, and there's stress related to finances. Oftentimes, when I feel the pressure of financial responsibilities, what empowers me is a change in my outlook. I dislike feeling boxed in or forced into anything, including a job or professional role, simply out of financial need. So my mindset has to shift.
I've had to take jobs that I didn't necessarily like. I've also been underemployed before. The key was to think about the goal and focus solely on that. Whether it was to pay off a debt, tide me over while I was in a time of self-employment slump, or save up for a large purchase, focusing on the goal vs. my dislike of the actual job, helped me push through and be more strategic about my career moves.
Once I was able to meet certain goals, I found the freedom to be a bit more picky with the organizations I work with, the companies I work for, and the salary I was willing to accept. It might take a bit of time, but you can set yourself up for this freedom with strategy and focus.
The optimistic piece is key here because it's easy to fall into a cycle of thinking about the negatives of a job or career. It's also easy to fall into shame about mistakes made or about what you perceive you lack, but when you shift focus to what you can control, what you can change, what you do have, and your end goal, you're better able to really be strategic about going for the professional life and quality of work you'd like to have.
JLco - Julia Amaral/Getty Images
2. Get to know what really motivates your fulfillment or happiness at work.
Do you just generally like helping people? Do you like challenging yourself intellectually? Do you love working with children or being a person of authority? Do you like being outdoors or doing work activities in nature? Do you enjoy solo work where you really don't have to interact with too many people all the time? Is your work purpose-driven or more about making lots of money? (It's totally fine to be motivated by the pursuit of financial freedom and wealth, but you must keep it real with yourself in this regard. We all play various roles in this world, and the money-makers among us are vital as well, so there's no shame in that.)
Sit down and think about these things. Write them down. If your current job or career doesn't align with what motivates you to get up and take action every day or it doesn't involve tasks that will guide you to your ultimate goal in life, consider looking for other work, going back to school to get training in something else you might be interested in doing for a living, volunteering, or taking on other projects at your current job in order to really tap into what you enjoy doing.
3. Find other fulfilling activities that fill in the gaps of dissatisfaction.
Some of us can't afford to just quit a job or give up on the years we've dedicated to a company. That's fine. If there are things about your job that are stressors or that are simply just a norm in the work you do, find other activities outside of work that allows you to have some sense of release and balance. It could be sports, spa dates, exercise, church, family time, or solo do-nothing days.
It could be starting a side business, a nonprofit, or a group for other people who have similar interests. It could be therapy or other spiritual practices. If you find you've made your job your whole life, it's a good idea to figure out a better balance so that you aren't consumed by it.
It's great to be an achiever and to do well at work, but there are other human needs that are important, too. Deliberately schedule other activities on your calendar and make them a priority so that you can start to really enjoy your career by having a balanced outlook on your role in it.
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4. Use your voice---especially if you're in a leadership position---and ask for help.
Oftentimes, it can be hard for us to simply as for the help we need. We don't want to seem inadequate, inexperienced, or, dare I say, weak. We want to seem strong, powerful, and resilient all the time. And that desire is a valid one, especially due to the discrimination and toxic systemic issues we face in the workplace.
I challenge you, though, to ask for help, anyway. If you need an assistant, ask for one. If you need time off, ask for it. If you need more time to complete a task, ask for it. Build your tribe at work and get support. Even if you feel your manager or supervisor will say no, speak up anyway.
We have to get into a practice of speaking up because the more all of us do this, the more we empower ourselves and help to shift company cultures. It's really annoying and sometimes insulting to have to justify a reasonable request for assistance, but sometimes, it must be done.
I once had to create a whole pitch just to get an intern to help with the work I had in managing projects that probably should have been split between three people, not one. I ended up getting the intern, but just having to create this whole pitch for something a leader could have used common sense to approve was a lesson in humility for sure. It was as if I had to prove I deserved an intern or help at all.
If you're a manager, delegate. Trust others to do tasks. Empower them by giving them the tools they need to fulfill certain obligations that are really distracting you from the more vital deadlines that you need to meet. Being a superwoman is just not realistic, and to be honest, it's a farce. A true leader serves and is able to give others a chance to be leaders within their own right. You can let someone else shine without dimming your own light.
And managers, speak up for more efficient work processes, better ways to communicate, equal pay, and better protocols that put workers who offer amazing talent and time first. If you have to take baby steps to do this, do it, even if you must align yourself with a privileged ally or seek legal counsel. Again, change in terms of the fight to survive in a career or thrive in one can be sparked with one action from many of us.
5. Quit. Yes, just let that job go.
Burnout is nothing to play with, and it can literally affect your physical health. If you find that you're always mentally exhausted, are oftentimes depressed or angry, or you're coping with work-related stress through overeating or over-indulging in other ways, it's time to take a full stop. If you're literally at your wit's end and you have the family or other support to resign, do it. Talk to your family, a counselor, or a mentor, and take the steps to prep for an exit.
I'd had a point in my life where professional burnout literally led to a mental breakdown. I was in my early 30s at the time. I was overweight, drinking a lot, angry all the time, and wasn't sleeping well. I was working all the time as well, and I was not enjoying my life anymore. I called my mom. "There's something wrong. I cannot function. Ma, it's getting bad. I cannot do this anymore." She simply replied, "Come home."
I felt ashamed and like a failure, but looking back, several years later, it was the best decision of my life. My mom, stepfather, and grandmother really helped me during a tough time. I cashed out my 401K, got on unemployment, and rebuilt. I found love, bought a car (in cash, sis!), went to therapy, moved into my dream home, traveled, and made more money than I had when I was at that previous job where I'd experienced burnout. (I found balance again, both emotionally and mentally, and I felt like myself again.)
If you have the support, tap into it. Use all resources afforded to you to be able to take some time off to get out of survival mode. Change your environment.
And maybe your "letting go" doesn't even include quitting outright. Focusing on the positive outcomes, explain to your HR department or manager, and ask to take a sabbatical. During the break---where your job would still be waiting for you upon your return---map out what you want out of your career, what gives you joy, and what it will take to get your finances in order. Let go of the shame and get the help you need.
As Black women, we deserve all the best life has to offer, and while we must work hard and continue to challenge ourselves, we must also find fulfillment and joy within our career journeys. I hope these tips will help many of you take back your life and thrive.
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