How to Shop Like Insecure's Issa and Molly

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HBO finally brought a realistic portrayal of educated young black women to prime time with this fall’s addictive run of Insecure. Led by the show’s multi-talented co-creator, Issa Rae, the series centers around two best friends, Issa (Rae) and Molly (Yvonne Orji), as they struggle to find their footing in their love, work, and friendship in and around Los Angeles.

When the first episode opens, Issa is questioning both her relationship with Lawrence (Jay Ellis) and her career path at a nonprofit where she’s viewed as the token black girl who can decode pop culture (“Issa, what does ‘on fleek’ mean?”). Molly may be killing it at work as a corporate lawyer, but she’s unlucky in love as she finds something wrong with every guy she dates, refusing to see that she might be the common denominator in that equation. The first season was funny, chaotic, and above all else relatable — not just for the frustrating comedy of errors that ensued, but also for the clothes they wore while it happened.

From the pilot through the finale, each character has a totally distinctive personal style, from Issa’s closet of casual vintage to Molly’s modern power suits to the printed cotton J.Crew of Issa’s coworkers. Everyone on the show, even the secondary characters, mix high and low pieces in a way that feels true to life.

Clothes also help tell the story, whether juxtaposing Issa in jeans and Converse with Molly in silk and designer heels or showing Lawrence’s confidence grow as his career gets on track by moving from 3XL sweats to slim-cut suits. There are winks to pop culture in the form of graphic T-shirts made by black artists, too. And from Issa’s tees and jackets to Molly’s date-night mini dresses, these are all looks we’d cop.

To learn more about the clothes on the show, I chatted with Ayanna James, Insecure’s costume designer and Rae’s personal stylist. Here’s what she had to say about the inspiration for each character’s look, where she shopped for them, and other behind-the-scenes details from dressing the cast.

Turns out, emulating the style of your favorite character is not impossible — a bunch of looks are still shoppable. We highlight some of the best below.

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Photo: HBO

Racked: When deciding on particular looks for different settings and characters, what was your process? How do you keep each character's personal style in mind?

Ayanna James: Right off the jump for the pilot episode, we had to let you know that we are following two black women in Los Angeles. So we wanted to shop brands that were here in LA For Issa, we went to What Goes Around Comes Around and got her a pair of vintage Levi 501s. The jacket she wears in the pilot, that’s from my closet.

Certain characters would shop at certain stores, so, we went to those stores. [When dressing the characters with looks that had been pulled], we knew that nine times out of ten it was for a specific character.

For example, if I saw something from Free People, I know that would be either Frieda [Issa’s coworker at We Got Y’All, played by Lisa Joyce] or Joanne [Issa’s boss, played by Catherine Curtain]. They wear the prints and the cottons. If it was a pastel suit, that’s Molly’s world. If it’s an interesting jacket, that could be Issa. Each character had a very specific look, a style that was different from the rest of the cast.

What were some of your inspirations or reference points for the styles on the show? Did you look at other black shows or movies? I noticed some similarities to ‘90s and early aughts shows like Martin, Girlfriends, and Living Single.

A week before we started shooting, I binged watched A Different World. I had my notebook and wrote down fashion moments that jumped out to me and what was going on in the scene. I saw each character had a very, very, very distinct style and I loved it. Whitley would never wear Julissa’s jacket. It felt like those were really the actor’s clothing.

Shows like Martin frequently used HBCU [Historically Black Colleges and Universities] T-shirts on their actors. I’m a [Florida A&M University] Rattler, and I could easily identify the type each character represented and that played out in the clothing as well. I remember being proud when I saw FAMU get their shine. I wanted to give that same feeling to Issa’s audience.

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Photo: HBO

How did you pull together Issa’s look, and where would her character like to shop? If viewers are aiming to channel Issa's style affordably, what would you suggest?

Issa doesn't have a lot of money — she doesn’t make a lot of money working for a nonprofit. So a lot of the stuff she has is stuff she’s had for years, maybe from Molly. She would be going to thrift stores and vintage stores. Issa’s world is supposed to feel more lived-in, a lot of her stuff should’ve felt old.

[Her style] is supposed to come off feeling very average — that girl that goes to the mall, to Zara, Wasteland, Jet Rag, Crossroads, and boutiques. Issa would love Target. She would love Converse. She would have fun in a Levi's store. American Apparel would be the store she would go to. She's not working with a lot of money. Whatever's comfortable, whatever's cheap.

On the actual show we used everything from Isabel Marant to Opening Ceremony. She wears Stella McCartney as well — that denim romper that she wears to Career Day, that’s Stella. I got stuff from costume houses, from Wasteland, Bloomingdale's. I ordered stuff off the web for her. So Issa’s world is a lot more chaotic. Her style is everyday wear, so we could go kind of anywhere for Issa.

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Shop Issa’s Look:

Were you involved with selecting Issa's hairstyling? The range of looks shown throughout the season was refreshing.

Issa’s hairstylist is celebrity natural hairstylist Felicia Leatherwood. She’s styled everyone from Will Smith to Ava DuVernay. We work with Issa both for the show and her life. Felicia will meet up with me at the start of every day and we’ll go through the looks I’ve chosen and bounce ideas around and inspiration photos. Most times her ideas are spot on. Felicia accomplished showcasing contemporary natural hairstyles on a premium cable channel. Boss.

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Photo: HBO

What was Molly’s look, and where did you shop for her? Would her character have a favorite designer?

Molly’s aesthetic is very simple and plain, but it’s a statement. A lot about her makes a statement. She would shop at Neiman Marcus, but she wouldn’t want your average Gucci. She would get the nuanced and unique designer labels. Molly would love a Cushnie et Ochs. Her jewelry would be Ann Sisteron — really awesome, unique, fancy, interesting jewelry with diamonds in it.

At work in the pilot, they called her the “Will Smith of corporate.” She's always got to look on point. Her looks are pastel, blush, or soft-colored. Molly’s work looks are mostly ASOS, Reiss, and Ted Baker. A couple of times, we pulled some higher-end designers like Stella McCartney — we had some suits from there. I pulled some Polo for her.

Now, for outside of work on her dates, Molly is the type of girl who would go to Opening Ceremony. She would shop at a lot of high-end boutiques. It’s not like she went to Bloomingdale’s. The AKA jacket that she wears, that green jacket is something I got from ASOS.

[To shop her looks now], I would go to Zara and ASOS. They’re really easy to order from within two days and they have really good suits. We got a lot of her suits tailored, because Molly is very put together. You can get any of the denim she wears from Frame.

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Shop Molly’s Look:

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Was the difference in style between Issa’s two love interests, Lawrence (her boyfriend) and Daniel (her ex-boyfriend), done on purpose?

That was definitely on purpose. Daniel (Y’lan Noel) is an artist in the music industry. I didn’t want him to be the typical producer, the beat-maker you see on television that’s a hip-hop guy. I wanted Daniel to have an artsy feel, so on Career Day he wears a shirt with a Mandarin collar and he wears Chelsea boots and skinny jeans. Also, we just wanted to show how attractive Y’lan Noel is, so a lot of his shirts were fitted.

We wanted to channel more artsy artists, your Kanye Wests, A$AP Rocky types, who take time to look at their fashion.

Photo: HBO

With Lawrence [Issa’s boyfriend], you should see his progression from being on the couch for four years to getting a temporary job to interviewing and getting a job. Lawrence goes from 3XL sweatpants to J Brand jeans. He's feeling more confident, but he's also your tech guy, so he doesn't really pay attention to fashion.

Once he gets a job, we shopped mostly at The Kooples for him. Because by this time, Lawrence had been working out, so his physique is a lot better — he's tall and he’s muscular. So we shopped with mostly European designers for Lawrence. His suit that we used [in episode 7] is a beautiful Vivienne Westwood suit. It had a waistcoat built into it that we cut out. We put Daniel in all black from Topshop.

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Shop Lawrence and Daniel’s Looks:

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How did you use clothes to make characters more relatable?

I used T-shirts to talk about pop culture. Issa’s “Formation” T-shirt from @Popaesthete was a hit. Every 20/30/40-something-year-old woman got their life when Beyoncé’s album dropped. I knew people would relate. Another moment for Issa is in episode 8 when she’s pining for Lawrence and stalking his social media. She’s wearing his Hoya shirt. That part hits hard, because as a woman — I know I wear my significant other’s clothes when he's gone.

Was it important for you to highlight artists like Cristo Saez (who made the “Formation” shirt) and Kashmir Thompson?

Yes, because the “Formation” T-shirt was a nod to Melina Matsoukas, the show’s executive producer, who directed that episode [and Beyoncé’s “Formation” video]. And the Kashmir Thompson ADW T-shirt was a nod to Debby Allen, who directed that episode. We live in a world now where I get a lot of my fashion information from Instagram or Twitter. So you’re able to find really interesting, nuanced, and Etsy-type items.

I think we as people of color we tend to support, and everyone saw that Kashmir shirt and said “I need that.” It’s something to highlight the artists doing dope work. One, to give context to the show and homage to people who are really out here grinding to put on good black film and television. But then to also promote and showcase really amazing artists.

Photo: HBO

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This interview has been edited and condensed.