5 Tips for Looking Secure AF From the Costume Designer of HBO’s Insecure


When celebrity stylist and costume designer Ayanna James first started her career in fashion, she landed what she thought was a pretty plum job as an assistant to a big-name stylist. But as it turned out, this job wasn’t the starting point on a neatly paved road to career success; after four months, she was fired. “You’re going to make mistakes and embarrass yourself. Let it happen,” Ayanna says, looking back on that experience. “Then pick yourself up and go harder.” 

Go harder, indeed: In the wake of that devastating blow and facing the harsh prospects of joblessness, Ayanna started reaching out to everyone she knew in the industry. And sure enough, that hustle bore fruit: a week later, she was asked to style rapper B.o.B for the VH1 Music Awards. From there, she continued to grow her list of clients--one of which was actress Issa Rae, who at the time was building buzz with her web series Awkward Black Girl.

As Issa’s show picked up steam and was eventually adapted to become the hit HBO show Insecure, so did Ayanna’s contribution to it; as the wardrobe designer for the show, her personal, pitch-perfect looks added additional dimension and depth to the already complex characters. I was thoroughly obsessed with everything Issa wore, from her vintage “When Doves Cry” tee, and lobster-and-hot-sauce shirt, right on down to her granny panties. And Molly’s closet is just as covetable, stocked with Opening Ceremony and Cushnie Et Ochs.

As someone who’s spent a lot of time thinking about two ambitious young women looking to find their footing in the professional arena, Ayanna has valuable insight into that decision-making process. I reached out to her to find out how she would dress Issa and Molly--who have drastically different styles--for a job interview. “Molly’s very fashionable. Her shoes would be designer and she would have beautiful yet simple jewelry,” Ayanna explains. “I would probably put Issa in Jack Purcell Chuck Taylors with a nice blazer and some skinny jeans. Issa is very smart and good at what she does. I would want her new employer to see her for who she really is.” 

Running with that, we asked Ayanna what you should wear in order to impress a prospective client or employer while staying true to who you are. Here are five basic things to keep in mind:


1. Start with the basics. “Have a classic slack in navy, black and a neutral gray color. You don’t have to buy a full suit. You can mix and match the set to create a variety of looks.”

2. Splurge on a classic black pump. “Spending the money up front will save you from having to replace shoes. Plus, people notice a good shoe.”

3. Don’t let accessories distract from the overall look. “We all have a pair of earrings or a necklace we love. Make sure your look is cohesive and the potential employer isn’t ignoring your resume because of your bright earrings your boyfriend bought you last Valentine’s Day.”

4. Do you. “If you work in a more creative industry, do you, full-throttle. If you love Converse, wear a really nice pair to your next interview.”

5. Tailoring is everything. “Suiting is not made to order; very often the difference between a good look and a great look is a suit that actually fits your body. Go to your local seamstress and handle it.”

-Zio Baritaux

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