The stylist behind the award-nominated breakout HBO hit discusses all the subtle fashion clues fans may have missed
Credit: HBO

If you haven’t heard of Issa Rae by now, block out your weekend to catch up on the actor/producer/writer’s credits to date, including her viral web series and book The Misadventures of Awkward Black Girl – and of course, her new smash hit HBO show Insecure which has already garnered her a Golden Globe nomination for Best Actress in a TV Comedy or Musical. (You can also get a crash course here.)

But while it seems like there’s nothing Rae can’t accomplish, she couldn’t get it all done while looking so effortlessly put-together without the help of her longtime friend and stylist Ayanna James, who also serves as the wardrobe designer on her web series and TV show. James spoke to us about her unusual start in fashion, creating the stylish world of Insecure, and all the sartorial excellence you can expect to see from Issa in the seasons and awards shows ahead.

Though she’s now the stylist to one of the hottest new names in the industry, James actually got her college degree in bio-chemistry. After moving to Los Angeles with her family, she began to find her place in a new city in a very millennial way: by starting a style blog. As the blog began to take off, James says, “I saw Dwyane Wade’s stylist tweet one day – this was probably five years ago – that she needed an assistant. So I just tweeted her back and she brought me in, interviewed me, and hired me on the spot.”

About a year later, she met Rae or the first time after a photographer friend asked if she’d like to style a photo shoot he was doing with the Awkward Black Girl actress. From there, the stylist says, “We kind of just kept in contact and then when she got various projects she was working on, she’d call me in. But Issa and I at the time were still building ourselves so it was easy, I could get practice on her productions and she got a costume designer. So for years I’ve just been working on her smaller projects.” And both of their profiles have grown from there, James adds: “It’s the best thing to see the hard work that she’s put in, and the world is finally catching on to her genius.”


In terms of how much work actually goes in to dressing Issa, however, James insists it’s pretty straightforward. “She’s very basic. Like extremely basic. I tell her all the time, ‘Can you want the nicer things in life?'” she says with a laugh. “Issa is all about her work, so her personal style is very comfortable because, especially now, she’s got a lot to do. Typically she wears Converse, skinny jeans, a T-shirt and a jacket I bought her. That’s her everyday uniform and that’s it. She doesn’t want to dress up, she doesn’t want me to do anything more. Even with the success of the show, you would think she would go spend money — nope!” But, the wardrobe designer adds, Rae’s simple style stems from a history of always putting her job ahead of her self.

“In a way [Issa]’s self-built. She put the work first so regardless of how she shows up in any space, people love her because of the work she’s put out,” she says. “So on the show and when I’m dressing her in regular life, I try not to overdo it because that’s not her, it’s going to read funny and I want people to understand who she is, not just the character on the show.”

In terms of differentiating between Insecure Issa and IRL Issa, James says, “When I interviewed for the show, we discussed how we wanted her to look. [Issa] said, ‘I want to look like me, but better.’ And to me that meant being comfortable, but put-together. The fit is good, the colors look good, all of that. So it was really easy to play with her wardrobe because I’m already familiar with it, but it was a lot more fun because I had an HBO budget.”


But even though James swears Issa isn’t picky, there are still plenty of things she refuses to wear. “In real life, her biggest concern right now are her feet. She’s got big feet; she wears a size 12, so it’s hard,” James says. “A big thing is always making sure she can walk. She doesn’t like high heels, she’s not your typical girly girl. She doesn’t like anything that’s too fashionable. But I think if I could dress her in anything, I would polish her up. I think Issa’s positioning herself to be another Shonda Rhimes and so in addition to this amazing quirky, funny television show that she acts in, she’s a boss behind the scenes. I’d like to put her in brands like Theory or Stella McCartney that still give you a bit of funk and tomboy-ness.”

James says that the most important part of her job on the show, for her, was creating a world that looked and felt entirely authentic, playing with the subtleties of fashion to help each character fully convey their story. She adds, “I love seeing the viewers pick up on the little nuances I placed in wardrobe. I’ve seen a couple tweets that say, ‘Lawrence is always wearing a Georgetown t-shirt, but can’t use any of his connections to get a job, like, what’s going on?’ I thought that was hilarious, but that was also what I wanted! I wanted you to question what happened that would make him sit on a couch for four years and not get off his butt and work.”

Credit: Courtesy of Ayanna James

She continues, “I think [my job is to help] relate the character’s story, to make it feel personal, so when the audience is watching they feel like, Oh, I know that person. That was the key in the choices I made for all of the characters. Issa’s world is a lot more color and texture, playing with prints and patterns. Molly [played by Yvonne Orji] is more pastel; her world is very sterile and clean, but as she begins to unravel, you see her colors beginning to darken a little until we get to episode seven where she’s having the blow-up with Issa and she’s wearing all black. For Molly, all of that pent-up frustration played out in her wardrobe. And then her and Daniel in episode seven are both the anti-heroes, so Daniel shows up in all black too. I saw in my head the scene with him and Lawrence and I wanted it to be clear that this was a choice between Issa’s past and her present and the past was kind of a dark, muddy situation – like: That’s not where you want to go Issa, that’s nothing but trouble.”


Over the course of her career, she adds, there’s one major lesson she’s taken away from her experiences being her own boss and that’s, “You’re always learning.” And where better to get that on-the-job training than on Sunday when Issa hits her first major red carpets for the Golden Globes.

Make sure to head back here for all of the exclusive behind-the-scenes photos and your first glimpse of what dress this duo decides on for the big awards ceremony. Though no matter what they choose, we’re sure Issa will look, as her character would say, “cute as f–k.”

What do you think of Issa Rae’s style both on and off the show? Did you watch Insecure? Do you think she should win a Golden Globe? Sound off below!