Five Questions for Issa Rae’s Makeup Artist

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Joanna Simkin on the star’s glowy skin, collaborating with Vera Wang and the duo's music ritual.

Before Issa Rae’s breakout HBO show Insecure premiered in fall 2016, makeup artist Joanna Simkin and the show’s star had already hit it off. “It was the very first press and promo run for season one,” says Simkin of working with the newly anointed face of CoverGirl. “We clicked immediately—she's awesome and inspiring and SO gorgeous!” Here, the artist opens up on the story behind Rae’s flawless Emmys makeup.

What was the inspiration for today's look?

Today's look was inspired by Issa's luminous skin and the vibrant red dress she wore. We wanted to keep the makeup look smoldering but still understated, with glowing skin. The CoverGirl Vitalist Healthy Elixir was ideal for this — it was buildable yet still kept the skin hydrated and gave that perfect glow.

What is the focal point of the look?

Issa's luminous skin is always the main focus of our looks — she simply glows. For her eyes we wanted to make them the true focal point so we went for a smokier look tonight. Which paired perfect with her glowy skin.

Any tips for re-creating the look at home?

CoverGirl Vitalist Healthy Elixir Foundation in Soft Sable were key to maintaining flawless luminosity. The coverage is buildable, which allowed me to customize her skin and maintain its natural luminosity. 

Additionally, CoverGirl Lash Blast Volume in Black  allowed for definition in her eyes without having to intensely smoke them out with shadow. The formula really gets every lash and enhances the shape of her eyes beautifully. 

Did you and Issa collaborate on her makeup?

The really fun part of creating tonight's look was that not only did I get to collaborate with Issa, but also with the legendary Vera Wang, whose dress she wore. Getting to hear a red- carpet master's vision for her couture dress was so inspiring — Issa and I both loved her suggestions and followed them pretty closely!

What was your getting-ready soundtrack?

Ha! I always tease Issa that she runs with a playlist of hip-hop songs that I just press "skip" on. It's become a ritual for her to find the most annoying (to me) and hottest (to everybody else) song out and blast it as I roll my eyes and we crack up. I prefer ’90's hip-hop myself. Today we met in the middle with Drake.