Easy, Breezy, Beautiful Issa Rae: How the CFDA Awards Host Rocked a Flawless Red-Carpet Face

Issa Rae attends the 2018 CFDA Fashion Awards at Brooklyn Museum on June 4, 2018, in New York City.
Issa Rae attends the 2018 CFDA Fashion Awards at Brooklyn Museum on June 4, 2018, in New York City.
Photo: Dimitrios Kambouris (Getty Images)

Call us obsessed, but we can never seem to get enough of Issa Rae’s seemingly endless array of stunning red-carpet looks. The star’s hosting gig at Monday night’s CFDA Awards provided yet another opportunity for us to gawk at her flawlessly executed face and fashion sense, which is now almost in another stratosphere from the more down-to-earth style her adorable alter ego, Issa Dee, sports on Insecure, which will return to us in full force on HBO on Aug. 12.


Until then, we’re going to revel in Rae’s red-carpet evolution, which reached new heights Monday with a disco-inspired look, pairing a custom-made, crystal-encrusted cobalt chiffon jumpsuit (with a sweetly subversive message) by Kerby Jean-Raymond for Pyer Moss with a sparkly eye, flawless skin and a slicked-back, extra-long, naturally textured ponytail.

First off, let me tell you: Rae and longtime stylist Felicia Leatherwood just inspired me to revisit one of my favorite warm-weather looks, which has been safely ensconced in a drawer since its last wearing. That’s right: When the mercury rises, I like to keep my glamour as low-maintenance as possible, and a naturally textured drawstring ponytail always does the trick without breaking a sweat—or my budget.

Speaking of budgets, how dope is it that Rae’s red-carpet glamour can now be achieved via the drugstore aisle? Since Rae officially became a CoverGirl campaign star last fall, we’ve been able to easily hop down to the corner to experiment with her looks within hours, thanks to the steady stream of tips generously provided by Rae’s super-talented makeup artist, Joanna Simkin.

After Rae made her dazzling debut on the CFDA step-and-repeat, Simkin graciously posted a few product details on Instagram, and we began taking copious notes.


But because we know there’s more to Rae’s flawless face than just slapping on product, we went in search of a few details, and score! We found just what we were looking for on Allure’s website, where Simkin not only listed the products she used to create Rae’s winning CFDA Awards look but also gave some insight into her technique:

Get That Glow

“I wanted to go for a really moist look, so I used a lot of hydration at first,” Simkin told Allure. To enhance that luminous skin we were all swooning over, she relied on cult favorite Embryolisse Concentrated Lait Cream, applying it all over Rae’s face.


Be Strategic

As much as we love a glow up, too much glow can end up looking greasy. To tone down Rae’s T-zone, Simkin used CoverGirl’s new TruBlend Matte Made Liquid Foundation in the center of her star’s face to keep her camera-ready and shine-free.


Don’t Blush

A rosy flush is ideal for some looks, but Simkin went another route for Rae’s CFDA look. “I wanted to keep the skin really neutral and golden because the eye is so strong,” she said. As an alternative, she used CoverGirl’s Queen Collection Bronzer for warmth on the perimeter of the face, playing up Rae’s already fantastic bone structure before following up with the brand’s Vitalist Healthy Glow Highlighter in Sunkissed to subtly highlight Rae’s cheekbones, brow bones and chin and the bridge of her nose.


Look Like a Boss

“We gloss, we floss, we boss” is our motto here at The Glow Up, and there has never been a boss more glamorous than “the Boss,” Diana Ross, who was Simkin’s inspiration for that incredible sparkly eye meant to mirror Rae’s Swarovski-studded jumpsuit. To start, Simkin focused on structure, ’70s style:

I started by using the browns from [CoverGirl’s] Chocoholic Palette to carve out the crease which is more exaggerated and darker on the inner corners rather than on the outer corner. It kind of goes up above her natural crease and heads into her nose contour.


Get Crafty

To ensure that Rae’s eyes had a true disco ball effect, Simkin turned to an art-store staple now readily available in makeup-grade versions: “I took a regular silver glitter and wet it with the CoverGirl Look Lock It Up Spray and then pressed it all over the lid until I hit the crease,” she explained.


To make Rae’s lashes worthy of the Boss, Simkin first used lash primer, which she then topped with several liberal coats of CoverGirl’s Flourish by Lash Blast Mascara. (We’re guessing a few false-lash pieces were also added, for extra impact.)

Know When to Go Nude

With all of that eye drama, a strong lip would have been too much look. Rather than compete, Simkin complemented Rae’s bronzed skin tone with CoverGirl’s Exhibitionist Lipstick in Coffee Crave, even skipping lip liner to keep the effect sexy and soft. “It’s the perfect brownish nude and is the most gorgeous color,” she told Allure.


After a misting of setting spray, Rae’s look was locked in place—as was her hold on the title of best CFDA look this year. And that’s nothing to be insecure about.

Maiysha Kai is managing editor of The Glow Up, host of The Root Presents: It's Lit! podcast and Big Beauty Tuesdays, and your average Grammy-nominated goddess next door. May I borrow some sugar?



1) Start with naturally gorgeous face.

2) Add makeup applied by a pro.

3) Perfection.