Getting Ready

How Issa Rae Gets Ready for a Big Event

Talking awkward red carpet moments and inappropriately long hugs with the Insecure star.

By: Noah Lehava
Photography: Nikko LaMere

“With my makeup I like a more natural beat, and Joanna [Simkin] knows how to give me the natural, classy glow I love. And Felicia [Leatherwood] always improvises or comes up with an idea [for my hair] the day before based on the event. She came up with this look while she was in the shower and voilà. Hair.”

Her getting-ready ritual:

“I always play my music and walk around in a robe of some sort. Most times I’m naked underneath (sorry, glam squad), so I feel like a canvas. I love knowing that I don’t have to think about shit but the songs I’m hearing and knowing that the squad will work their artistic magic to my delight.”

“[I’m most excited about] being with my Insecure family and partying with all of the people that I watch on TV. I’m so proud of the talent being awarded this year and so honored to be among them all. And I’m excited to drink a lot of champagne. I may not win, but I will for damn sure be drinking with my friends.”

“I hate making decisions [on what to wear]. I trust my stylist, Ayanna James. She usually provides options and judges by my look or my body language whether I’m messing with it or not. This was one of those dresses I put on and I felt good, like ‘okay!’”

“I would fan out over Viola [Davis] and Denzel [Washington]. I haven’t officially met them yet and I would just tell them I love them and to keep it pushing. I love Kofi Siriboe from Queen Sugar. I would give him a long, inappropriate hug.”

“I loved Hidden Figures and Moonlight. If either of those win then all is right with the world.”

On her pre-game playlist:

“It was a mix of Sampha, Big Sean, Solange, Drake and then all the ratché I love: Migos, 21 Savage, Uzi, etc. I [would call] it ‘Sophistiratch Sounds.’”

“[The last thing I do before walking out the door is] look in the mirror, put on some lotion or oil and spray my favorite Serge Normant perfume.”

“Getting Real”

We’re taking an honest look at love, life, and all the things that come with being an adult.

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