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When I spoke with Ayanna James, costume designer for Insecure, days before the second season of the series premiered on HBO, our conversation touched on all of our favorite characters. When she mentioned that one of her goals when costuming Molly Carter, best friend to Issa Dee and high-powered lawyer, is to elicit a “wow, I really want to dress like her” reaction from viewers, I thought for a moment about interjecting. Molly is definitely The Fashion Girl of this group of friends, with a wardrobe that we all might put on a mood board titled My Most Stylish Self, but James’ true gift has been making almost everything that she puts these characters in, from tees to sweatshirts to suits, the stuff of wardrobe envy and inspiration.
We seem to only get a seminal comedy series about black female friendship once a decade, in the 90s we had Living Single and in the 2000s, Girlfriends, and James was dedicated to helping make the world of these women, the type of women whom we do not often get to see front and center on our television and computer screens, full, complex, and layered. From the moment the pilot opens, James’ work does exactly what good costuming should. It aids, amplifies, and moves forward the story being told without overshadowing it. The clothes tell us something about who Issa, Molly, and Lawrence are and where they are by immersing us in their world.
When we meet Issa Dee, she is standing in front of a room of wildly judgmental middle schoolers. That sort of gauntlet is the stuff of nightmares but this is no dream sequence. This is Issa’s job. Issa’s “very insecure and her wardrobe kind of reflects that. She hasn’t really found her footing,” James said of the character in that first scene. Although we don’t know it at the time, this look, We Got Y’all Tee with a logo of James’ design, vintage Levi’s, and Solange Knowles for Puma sneakers, is something of a uniform for Issa when she is out in the field with the kids.
She isn’t a fashion girl, at least not in the same way as her best friend, Molly, but she is trying. The topper, a boldly colored, printed piece that lives somewhere between blazer and oversized cardigan, makes that effort apparent, and it actually came straight from James’ own closet. “I wore it to the interview when I met with Melina [Matsoukas]. She was like ‘I love that! Bring that back!’” James told me. But the rest of the look is inspired by the woman who brings the character to life. “We wanted it to kind of be true to Issa Dee and pull elements from Issa Rae. Issa Rae, on a day-to-day,” James said, “she’s dressed pretty much like that, a jacket, blazer, a cardigan, some jeans, a t-shirt. So we took her style and just elevated it.”
Molly Carter is playing a different career game from her best friend, and much like Issa’s iffy footing is immediately obvious, so is Molly’s nearly flawless navigation of the legal world. And it’s not just because we don’t have to cringe through her getting heckled by a room full of tweens. “White people love Molly. And black people looove Molly," Issa says in voiceover as Molly Carter greets the audience, first commanding a meeting and then dominating a game of dominoes. Her confidence shines through not only the way in which she slams down that final tile but also in the look that she does it in. In discussing Molly, James started to list some of the hottest brands around. Molly wears Balenciaga and Alexander McQueen. She carries a Salvatore Ferragamo briefcase and wears Fendi heels. And even without the introductory words of her best friend, we can see that she is a master of code switching. “Molly even code switches in the way she dresses,” James stated.
Not only at the office, where her light-colored palette demonstrates how she is “trying to fit in and go under the radar but [also] stand out,” as James put it, but also in her dating life. “When she’s out, I kind of made her a bit darker to give contrast from how she is at work. Because at work she has it all together, but in her dating life she tries to make it look like she has it all together but she doesn’t." At first glance, the Stella McCartney and Opening Ceremony and Jonathan Simkhai dresses that she wears when meeting men from dating apps or attending a disastrous engagement party with Chris, a character played by Jidenna, wouldn’t make clear all of the ways in which Molly thinks she’s failing at finding someone.
But that is what James has done. She has taken the central tenet of the series, the various insecurities that we all feel about adulthood, friendships, and our romantic lives, and translated each character’s struggles into palette and fabric and silhouette.
This skill is most apparent in her work with the character of Lawrence. He greets us on a couch, a couch he has been on for years, and James put Lawrence in 3X t-shirts and 3X sweatpants. She did this partly to show how little Lawrence cares about his appearance, and much of anything really, and partly to mask the thirst-inducing physique of Jay Ellis until it was time for Lawrence to complete his full aesthetic transformation. “I gave [Ellis] some socks and I told [him] to go walk around outside so that they’d be dirty." She aged the Georgetown tees that he wears. From head to toe, we can see that he has given up and in turn we understand why it is that Issa has started to give up on him. But the changes he makes, with the assistance of the costuming arc that James created for him, make us realize that we might have been hasty in our judgement.
“[B]y the time we get to episode four where he and Issa have recommitted to each other,” James said, “he’s interviewing, so he’s pulling out all these old suits that are just a little ill-fitted. But, you know, he’s trying. He’s going to do this.” James caps the transformation with the Vivienne Westwood suit that Lawrence wears to the We Got Y’all fundraiser, a sartorial indicator of his getting his life together. She puts Lawrence at his sharpest right before everything he made the changes for falls apart.
As the series moves into season two, James continues her exemplary work. We’ll see the fleshing out of the style stories of Kelli and Tiffany. Molly, dealing with the revelation that she is being paid less than her while, male colleague, “immediately goes into survival mode and her palette darkens,” James said but still with the “crisp, sleek, body conscious forms” that we now know as pure Molly.
Lawrence and Issa will be dealing with being without each other. “What does a guy look like when he gets his heart broken? He’s buys some new shoes. He gets a haircut,” James said. More specifically James will be drawing from Ellis’ own love of sneakers to up Lawrence’s shoe game. In season two, “Issa’s style is just out there. She’s trying to catch. You gonna see some leg. You gonna see some cleavage,” James said. She bought some current season looks for the dating but still pining Issa but mostly she wanted it to look like Issa was reexamining the clothing she already owned. She’s dealing with her turbulent life by rediscovering a part of herself that had become hidden. We see it at her party, in a dress with, skin baring, Molly-reminiscent cut outs down the middle.
We see it when she goes in search of Lawrence at Chad's house in a tight pencil skirt that leads Chad to ask Lawrence if "old girl" always looked like that. And we see it as the second episode comes to a close with Issa looking at the empty space in her closet left by Lawrence’s now absent clothes and filling it with those forgotten pieces of herself. Pieces that, with James’ deft hand, will be as covetable and narratively revealing as ever.