How Issa Rae's 'Insecure' navigates the workplace with style

How Issa Rae's 'Insecure' navigates the workplace with styleEntertainment

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Even when everyone on Issa Rae’s HBO comedy Insecure is being hella messy, they look hella good in what they’re wearing.

As the series gears up for its second-season finale Sunday (11:02 ET/PT), Rae’s eponymous lead character, best friend Molly (Yvonne Orji) and ex-boyfriend Lawrence (Jay Ellis) all handle the quotidian and the quote-worthy moments in different ways. But they share running storylines of being young, single black people trying to navigate the workplace.

The similarities end there, but there’s no denying that the clothes play an integral role in reflecting their on-the-job storylines in very distinct ways. 

Costume designer Ayanna James serves as the brains behind the sartorial operation, putting together highly-coveted looks for everyone from the main characters to extras.

“There’s definitely a style evolution because we have more understanding of the characters now,” James says. “We’re able to kind of see the messiness we’re experiencing in relationships and work.”

From Issa’s funky, laidback looks to Molly’s stilettos and power suits and Lawrence leveling up from a Best Buy polo to Silicon Valley chic, each of their styles is mirrored in their attempts at self exploration after two seasons of shakeups.

After a major breakup with Lawrence in Season 1 — and with her personal life in shambles — Issa remains   in her cucible with well-meaning but slightly misguided coworkers at the nonprofit “We Got Y’All.”

“Issa is awkward,” James says.  “She’s not comfortable with her fashion, she’s not comfortable with this new change in her life, but she’s throwing herself out there.”

Issa makes subtle style decisions that celebrate blackness in a for-us-by-us way, and her graphic t-shirts serve as cultural statements when her coworkers make her the token black person in the office or put their own spin on popular lingo or rap lyrics.

Molly “would probably be at Fashion Week right now, checking out the latest fashions even though she’s an attorney,” James says. “For her, it’s designer everything, and as long as it fits her body then it’s going to work.”

Molly seems to effortlessly float between the office and her personallife. With poise and pantsuits, she works hard for the money, often staying late while dealing with microaggressions from her coworkers and feeling the pressures of gender and racial discrimination.

And even if Molly doesn’t have it completely together in her personal (and sometimes professional) life, her closet tells a different story.

Her Season 2 style evolution is sparked when she realizes that her white, male coworker earns more than she does at their law firm. Goodbye, hot-pink power suits, hello traditional black and navy.

“She realizes that just being good at what she does isn’t good enough, so maybe she needs to switch it up a little bit,” James says.

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When we meet Lawrence in Season 1, he doesn’t even have a proper haircut, much less a job or a sense of style outside of his 3XL sweatpants, as he’s planted firmly on the couch.

Enter Season 2: Newly single, he sports a closet full of button-downs with a fresh haircut, and is settling into a tech job.

Stylewise, James wanted to explore “what does a black man in tech look like when he’s the only black man in the office?”

“No one else in his office dresses like him. He’s the only one who’s dressed up, yet he’s the one who’s overlooked right now,” James says. “There’s that angst that you feel, especially when you see him next to the coworkers who don’t put in as much work.”

That workplace angst shows up hilariously when Lawrence’s bosses ask about his Air Jordans instead of passing on his app idea.

Much like the show itself, the clothes have become a statement about everyday lives, both accessible and fun for viewers.

Costumes don’t “have to look like something out of a commercial or a magazine,” James says. “In the real world, we don’t always feel perfect.”

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