Issa Rae May Be a CoverGirl, But She Still “Glams Up” on Her Own Terms

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Courtesy of HBO

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In HBO’s Insecure, Issa Rae offers an unfiltered insight on the intricacies of being a young black woman in the world today, from navigating a career, her love life, and friendships, to how she presents herself—the clothes, the hair, the makeup, the confidence (or lack thereof). Irresistibly charming and universally relatable, Rae’s persona, first introduced through her web series The Misadventures of Awkward Black Girl in 2011, has become a cultural phenomenon. And considering that her raw identity is teamed with undeniably luminous beauty, it was a surprise to no one—except maybe Rae herself—when CoverGirl announced her as their new face last month.

As a woman of color, and with diversity and representation in beauty more topical than ever before, it’s an opportunity Rae doesn’t take lightly. Her message? “If I can do it, you can do it,” she tells Vogue, adding that CoverGirl’s new tagline is #IAmWhatIMakeUp, a hashtag riff on the words of Nobel and Pulitzer Prize–winning author Toni Morrison, resonates with how she takes ownership of who she is. But true to keeping-it-real form, Rae also makes no secret of the fact that she’s never been a textbook beauty girl. “Growing up, I didn’t have a relationship to makeup at all—it’s all very new,” she says. “But as my career has evolved, and I spend more time in front of the camera, I’m more experimental.” And while that’s translated to some decidedly glamorous red carpet moments—she made her Golden Globes debut sporting smoky eyes, an intricate braided updo, and a crystal-embroidered white Christian Siriano gown—you’re just as likely to find her with scraped-together hair and makeup, clad in her “regular self” uniform of a T-shirt, jeans, and Chuck Taylors. “I glam up on my terms,” she says. “I don’t feel the need to prove myself or live up to expectations that I don’t set for myself.”

But as both a woman and actress, Rae is attracted to the transformative powers of beauty. In the Insecure pilot, she hones in on the nuances of getting ready, whipping through a lineup of different lipstick colors in front of the bathroom mirror, encapsulating exactly how a classic red lip and off-kilter black-green shade recalibrate her vibe. “I love the way our director Melina Matsoukas shot that scene,” she muses. “It felt so authentic to me because when you wear a bold lip color, you feel like you can take on a different personality.” She views trying new textured hairstyles, from a crown of braids to a halo of corkscrew curls, as equally exciting. “Natural hair hasn’t been represented as much on television and film for black women, so to be able to showcase different hairstyles is amazing.” And it’s for these reasons she’s always admired chameleonic icons such as The Cosby Show’s Denise Huxtable and Rihanna. “We all watched her go from being the girl from Barbados breaking into the pop world to becoming an icon on her own terms. That’s an evolution I aspire to,” she says of beauty’s resident Bad Gal.

With a newfound appreciation for presentation as self-expression, and a fine-tuned roster of products including CoverGirl’s Vitalist Healthy Elixir Foundation and Aunt Jackie’s Don’t Shrink Flaxseed Elongating Curling Gel, getting ready has become a sacred ritual for Rae. And as Insecure fans who are addicted to the show’s soundtrack, which runs the gamut from R&B torch ballads by SZA to turn-up rap tracks by Ty Dolla $ign, can imagine, music is a vital part of the “glow up” equation. Her current go-tos before a night out include Frank Ocean (whom she pays homage to with lyrical Easter eggs in every episode of season two), 2 Chainz, and neo-soul rocker Nick Hakim. Update your Spotify accordingly.