From left: Molly (played by Yvonne Orji), Issa (played by Issa Rae), Tiffany (played by Amanda Seales) and Kelli (played by Natasha Rothwell).
The characters on Insecure don't dress like anyone else on television — and that's on purpose.
To call HBO’s Insecure buzzy would be an understatement. Created by Issa Rae (who is also one of the stars) the sharp, witty and boundary-breaking show explores the ups and downs of being single, pay inequality, gentrification and friendship with hilarious (and sometimes cringe-worthy) results. And it’s not just the deft writing, direction and talent of the cast that makes the show, which wraps its second season this week, a must-watch. The costumes bring the characters to life and tell a story that requires no words. We spoke to the show’s costume designer Ayanna James about Insecure’s most-talked about fashion moments, Gucci wedges and keeping the look authentic.
This interview contains spoilers for season one and two.
How did you get into costume design?
“I started out as a stylist, mostly for celebrities and red carpets. A colleague of mine was doing a small TV series and asked if I wanted to assist. I was like 'This is great, this is so organized.' I liked seeing all the different departments work together so I kept looking for more costume design jobs and assisting until Insecure came along. I was working with Issa already, and I went out for it. That’s how I got into the major leagues!”
What does a typical day on set look like for you?
“No day is the same, but it’s really jam-packed. While we’re filming, if it’s early in the week, I start at four in the morning and get to the set. I’ll meet with my department about the different looks for the day—who’s wearing what and how we want the background to look. Once the scene is established I'll have a meeting or more fittings or I have to shop. When working in television, most of the time you prep for the next episode while doing another and wrapping another one.”
Was there an evolution of the characters’ clothes from season one to season two?
“In season one, we’re just meeting the characters. We meet Lawrence in the pilot, he’s been unemployed for two years and he’s sitting on the couch. Issa is still in a relationship at this point but not really happy and wanting to get out, and she’s not happy at her job. In the middle of season one Lawrence gets a job at Best Buy, so his story arc changes a bit and now he’s off the couch and not in sweats anymore. By the finale, Issa and Lawrence have broken up and Lawrence works at a tech company. So I would say that Lawrence has the biggest arc in terms of storytelling and style. Issa and Molly stay pretty consistent in season one. In season two, when we pick up all the characters are in very different spaces. Issa is now trying to date, so her costume has changed because now she’s a single woman trying to put herself out there. We had to create a wardrobe that looked very real, like she would have had it, but that’s more geared toward her new mindset. And then of course for Lawrence we said that his flashy friend Chad, whose couch he’s been living on, has influenced his style a bit.
Issa and Lawrence
Yes, in episode five, he has that polka dot cardigan; he’s definitely a little bit flashier.
“Yeah, the Comme des Garçons. I made it so that Lawrence is still kind of corny. He has a kind of quirkiness. So how would that look on a guy that’s in tech, who for the last five or six years hasn’t had to impress anyone. And so, what does that re-emergence into the world look like?”
There was also that button-down that he wore when he bailed on Tasha’s family picnic.
“That was Kenzo. I get two or three emails a day about that shirt, from guys or their girlfriends asking where to get it.”
Tasha and Lawrence
Have there been any other pieces that have garnered a similar reaction?
“I get the most requests for Issa, Molly and Lawrence. For Issa, it’s every piece but mostly her T-shirts. I put her in a lot of vintage tees or shirts with pop-culture references. Everyone always asks about what Molly wears.”
One particular standout from season one was the dress Molly wears to the bridal shower.
“The Jonathan Simkhai dress. Coming up to the episode, I remember I hadn’t been able to find anything that I thought would really nail it. And then I was looking, searching, searching, searching online and I saw the dress and was like, 'Oh, that’s it!' And sure enough, I bought it, and everybody loved it, and a lot of people ask about that dress. A lot.”
And how has Molly’s style transformed from season one to now?
“I really fine-tuned Molly’s wardrobe for season two and stripped away anything that I felt didn’t scream fashion. In season two, we kept the momentum going where she’s in nice pantsuits. We shopped a lot of Theory for her. She wears a lot of Cushie et Ochs dresses. I reached out to some friends that have a label called M. Martin. When she finds out that her co-worker Travis makes more than her, it really frustrates her. So you see her clothing turn a bit darker. In season one we used a lot of light, pastel colours. And then after the pay gap episode, her suiting gets darker. Almost as if she’s trying to figure out how to join the old boys' club.”
Molly seeing her co-workers paycheque
With Molly’s going-out wardrobe, it feels like she’s dressing for herself. In episode five she had a cute denim dress with cut-outs. She was wearing what, I think, made her happy.
“For sure, I’m really particular about how I curate the wardrobe. I really don’t want it to look like anything you’ve seen on television. I don’t want people to think that Molly is like any other career woman. She’s very unique, and Issa is very unique. You have to be those girls in order to wear that wardrobe.”
Issa and Molly
And for Issa’s dating wardrobe, the montage of the Tinder dates, she progressively looks more casual as she loses faith.
“That was really fun. It goes from the fantasy date with Lawrence. Cut to a nice restaurant and she’s trying, then she goes to a not-as-nice Tinder date. And by the time we get to the last date, they are at a taco shop on the corner and she’s wearing converse, jeans and that sweater. So it was written like she would progressively stop caring.”
Talk to me about those Gucci wedges at the bar.
“Those wedges! First of all, that was in the script. [The writers] kept referencing wedges. And I'm like 'What is with this obsession with wedges?' But it’s supposed to be a hat-tip to Issa's awkwardness. Unless you’re a really fashionable person and you know how to properly pull it off, it’s not something women go to when trying to date. A wedge is like a comfortable sandal. I’m like, 'Well, if I have to use wedges, they’re going to be fly wedges.' Because I just can't use ugly wedges in the show. And so I bought a pair of Gucci wedges for her.”
In Issa’s own mind, does she see herself as someone fashionable?
“No, she’s not that type of person. You see an inkling of her trying different looks in the pilot when she’s trying out lipstick. She’s just trying whatever she thinks looks good.”
Issa's new look in season two.
You’ve said in the past that you imagine Issa going to a vintage store and buying a cool T-shirt. Or having something from college that she still wears. You are giving this extra dimension to her character without a scene that’s been scripted.
“I think that’s why people are able to connect with the characters because it doesn’t feel like a commercial. It doesn’t have any labels, it feels lived in, not brand new and shiny. We really wanted to create a world with a lot of texture.”
Does the L.A. setting play into how you’re dressing the cast?
“I take a lot from the city to influence how I costume the characters. Issa’s story is based in L.A., specifically the west side, Inglewood and South Central, Baldwin Hills and Crenshaw. I shopped based upon those areas. Issa’s earrings I actually brought back with me from a trip I took to Kenya two years ago. Anyone who knows L.A., knows that Issa’s workplace is located in a place called Leimert Park, which is a historical area in the Crenshaw District and they often have street vendors on the weekends. The earrings that I bought, even though they are from Kenya, look like a lot of the jewellery I tend to see in that neighbourhood. You’ll see a lot of her clothing looks like it could have been something she bought at one of the vendors where she is. Molly lives downtown. If you can afford to live downtown and an Audi, you can afford to shop on Rodeo Drive. She would, of course, shop at a lot of the labels there.
In terms of fantasy versus reality, you’ve put Issa in Gucci wedges and in another episode she had a Mansur Gavriel bucket bag. How do you balance that with what her salary might be?
"I'm lucky to have an executive producer who loves fashion. Melina [Matsoukas] will be like, 'I saw this, I thought it was cute.' I'll tie in designer pieces and style them in a way that it looks like it could be casual or something that she’s had for a while. I always pull pieces that, even if they are designer, look vintage or like something she found in her neighbourhood. But I like adding little accents like a Mansur Gavriel bag for fashion girls to geek out over.”
Are there any outfits from the past two seasons that are favourites of yours?
“Vintage T-shirts are one of my favourite things. I love to see how the viewers react to them. Everyone, of course, freaked out over the Humpty T-shirt, and a couple of people pointed out the visual irony of Issa trying to find batteries for her vibrator while wearing the Humpty shirt. So when the viewers catch it, it just makes me so happy. And anything Molly wears. I’m definitely going to dress like her when I grow up.”