Costume Designer Ayanna James Sees HBO's 'Insecure' as a Platform to Promote Indie Black Labels

The second season of Issa Rae's hit show debuts on Sunday night.
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Photo: Instagram/@hbo

Photo: Instagram/@hbo

HBO's "Insecure" returns for its second season on Sunday, bringing with it another promising lot of Issa Rae brilliance. With witty acumen, the show tackles a broad range of topics — race in the workplace, cheating, female friendship — with laser-sharp modernity, relatably reflecting what being a young woman in a major American city looks and feels like in 2017.

Similar to "Girls" and "Broad City" before it, the costuming on Insecure so accurately mirrors what ladies dress like today — contrast with, say, the hyper-glamorous "Sex and the City" — that it's easy to imagine each cast member showed up to set in her own clothes. In reality, it's the hard work of costume designer Ayanna James who brings Issa, Molly, Lawrence, and the rest of the cast to life with scene-specific outfits. Through fashion, James is responsible for rounding out each character's personality by assigning them a visual identity, something she collaborates closely with Rae on.

In advance of the show's season two debut, James was kind enough to walk us through the process of dressing the "Insecure" cast, from what goes into the nitty gritty day-to-day work of the job to using the show as a platform to promote indie designers of color.

Talk me through the development of the character of Issa Dee from the beginning.

Because I've been working with Issa for about five years now, I know the origins of where "Insecure" was birthed from and her work on "The Misadventures of Awkward Black Girl." Working with Issa Rae and being a huge fan, I went into "Insecure" having a really good sense of who this character was and that really helped to create the costume for the rest of the season. Anyone who has been a fan of Issa Rae and "Awkward Black Girl" kind of had an idea of the story, and I wanted to elevate that from a YouTube series to a series on HBO.

Season one was my first time designing a television show for a major network. I learned a lot from season one — and about what our viewers identified with, what excited them.

And what were some of those things?

They really, really love the T-shirts. The Beyoncé "Lemonade" hot sauce T-shirt was an instant classic; I'm constantly asked where we got Issa's Prince T-shirt, which I made. We shot that episode the weekend after Prince died, and my entire department was really affected by it. We decided we were going to give a little hat tip [to Prince] because everyone on the crew was a big Prince fan. And once I saw the reaction from the viewers, I was like, "Oh, they really appreciate that it feels authentic and close to home."

I reached out to a young lady named Kashmir who is an amazing artist who reinterprets celebrities but they don't have any detailing in their face; I bought a T-shirt from her that was of the "A Different World" cast and that was the episode that Debbie Allen directed, so in my head I was just giving a hat tip to Debbie Allen because she's so fucking legendary. That also generated a lot of conversation.

So from season one, I really looked at the metrics and the analytics of what engaged our viewers, what were they excited about, and for season two kind of upped the ante.

Photo: Instagram/@thatsayannaj

Photo: Instagram/@thatsayannaj

It's so cool that we're in this era where someone in your position is able to get direct feedback from the audience.

For real! I'm getting e-mails from people all over the world like, "Where did you get this shirt ... my wife loves this shirt ... I wanna buy it for her for her birthday," and I was like, "Oh wow, I'm actually touching people." That was a major motivation behind a lot of the costumes for season two.

"Insecure" is so multi-layered and has generated so much conversation — I think after the season one finale we were still trending on Twitter for like a week — and I just want to do my part and add to that with the costumes.

What is the collaboration process like between yourself, the writers, the producers? At what point do costumes come in?

We get a script, I read the script, I do a breakdown, and then it's really between myself, Issa, and [executive producer] Melina [Matsoukas]. We really just talk, so I'll say, "In this scene, where is Molly at or where is Issa at in her head?" And Issa, being the writer, will break down where she is, and then Melina will say, "Yeah and I kinda want it to look like this and feel like this." Then I'll go out and shop and we'll have another meeting after that. I'll give them ideas and tell them why I think it's a great idea. It's a very collaborative, family type of process in that it really is what Issa wants portrayed on television because, ultimately, these are her words. I'm just creating the world that she's written.

How much time do you get between seeing the script, talking through it, shopping for it, getting the looks together, and shooting?

I really don't get enough time! I don't get as much time as I would like to, but we normally have about a week.

At what point do hair and makeup factor into the process?

Felicia Leatherwood — who is Issa's personal hairstylist for the red carpet and on the television show — she and I have worked together with several clients over the years, so once I've gone through and I've selected and we've approved all of the looks, she'll come in and say, "Ok what's Issa wearing," and that's when we'll talk. Hair and makeup is like the cherry on top; [an] accent, but still very much as important as what I do in costume.

When it came to developing the character of Molly, who is clearly very different from Issa, what were some of the characteristics you wanted to communicate visually?

As far as the examples we've had on television, we have Kerry Washington on "Scandal," [as] Olivia Pope, who is a very popular character for her fashion, but that's somebody that is a bit more confident than Molly. The inspiration behind Molly was, "What would a lawyer look like if she was really, really into fashion? If she was the person who might take a weekend off to go to New York Fashion Week?" She lives in LA, she makes money, she works in an office that's run by the old boy's club, so how do we balance that to make it fashionable and make it relevant?

I've had quite a few attorneys reach out to me and say, "This is honestly how I want to look in the workplace, where do you shop for Molly?" There is a demographic that I've tapped into that is kind of relevant and current and interesting and new and that's what I'm having fun with.

There are such different rules for dressing in a work environment like that.

And if you were an environment where you're "the black girl" [and] you're really fashionable. I actually did work in an attorney's office in college, and I dressed to my taste [my clothes were] always a topic of conversation. I realized this was one of the nuances where black women add to the workplace, and we really wanted to showcase that with Molly.

In your own experience in that office environment, did you feel like it was a cool differentiator that you were someone who showed up to work in a look?

For sure! I remember my boss being like, "I totally just want to go shopping with you this weekend. You don't have to shop for me, but I want to go to where you go, I want to see your eye."

There's an emergence of a different type of black woman, and I think it's very interesting and it's worth diving into. You see that not only with Molly's character but with Issa; she's this girl who works at a nonprofit organization that's supposed to benefit disadvantaged children, but she also spits gangsta rap in the mirror. I feel like that is so relevant to so many women right now — to be that kind of ratchet and righteous balance. And that's what I really wanted to bring to camera.

I'm so excited to be seeing these new portrayals of what young women living in a major city looks like right now.

Right, and hearing that from you lets me know that we're doing what we set out to do.

Photo: Instagram/@hbo

Photo: Instagram/@hbo

What are some other shows and movies you admire for their costume work?

"The Get Down" — I thought was absolutely amazing. You could say period pieces in general; anything that's supposed to be very specific, because we live in a very commercialized and capitalistic society — mostly what you see [people wearing] is mainstream, watered down, not-specific, very easily digested type of fashion. It's supposed to be appealing to anybody, so I tend to veer away from that and love anything that's very, very specific. For season one on "Insecure" we were at a school that was set in Inglewood, so a lot of Issa's earrings and jewelry came from that area. That allows people who may not have experienced this side of the world have a peek in and see the humanity in it. And, ultimately, that's the purpose of storytelling.

Have you seen those websites that catalog everything characters wear on TV?

A couple of them have reached out to me, but I'm like, that's a lot of costumes! On episode one of season two there were 120 people with speaking lines. I don't have time to catalog that! But I do get a lot of e-mails and tweets as the episode airs that will say, like, "Where did you get this from?" and I'll tweet a picture and attach the brand.

Specifically with season two, I really, really tried to get as much indie, and black and brown designers as possible. Issa and Melina were very much on board and champions of [that effort].

That's so savvy! I was just talking to a friend about how some of the most important activism is the choices we make in our day-to-day lives, and this is such an amazing version of that. Like, you might significantly bolster sales for these designers.

That's so important to me! And it's so important to the crew because, like, that's where Issa came from. "Awkward Black Girl" was grassroots. It came from YouTube, it came from people sharing, it came from people talking about it, from word of mouth. Ultimately, I wanted to keep that core feeling that it didn't feel too Hollywood.

Knowing that I could possibly help a brand sell out [of a style] or get to that next level really is so important to me because I understand the concept of "lift as you climb." And because Issa has done that for me and for a lot of people on "Insecure," it's kind of like another way of paying it forward.

Ultimately, this is a show for us by us; that's the story that Issa has pushed, that we've all pushed comprehensively, so that is ultimately my goal within costumes and within wardrobe. If I've touched anybody I know I've done my job.