The Issa Rae Makeover You've Got To See

Issa Rae has been lighting up Hollywood with her hilarious brand of self-deprecating, wonderfully-honest humor since 2013, when she starred in the viral YouTube series, Awkward Black Girl. Flash-forward to today and we find Rae pushing the conversation even further for millennial women and female comedians alike with her megahit HBO show, Insecure.
Rae's show gives an intimate, forthright look at the topsy-turvy lives of two twentysomething Black women and earned the 32-year-old her first Golden Globe nom. Did we mention she's also the new face of Cover Girl and recently re-launched her culinary web series, Brown + Butter, on Aspire TV? At this point, we're pretty sure there's nothing Rae can't do.
Advertisement
In honor of this endlessly talented, role model-worthy woman, we recreated three of Rae's most iconic beauty looks from those low-key days as an internet newbie, all the way to her sophisticated Golden Globes glam game. Oh, and our look-alike hopeful just so happens to be a huge fan, too.
The goal? To replicate the way Rae's makeup always seems to capture the bold, playful spirit that's become her trademark, as well as her experimental approach to hair that we can't stop talking about.
Press play above to relive Rae's beauty evolution in a whole new way.
Advertisement

More from Celebs & Influencers

Watch

R29 Original Series

Watch Now
Documentary
Five love stories behind diverse, multicultural marriages.
Watch Now
Lifestyle
Life experiments, 5 days at a time.
Watch Now
Fashion
The style of subculture.
Watch Now
Beauty
Viral trends, tried and tested.
Watch Now
Documentary
From vibrators to lipstick, learn how your favorite products are made.
Watch Now
Documentary
Extraordinary, one-of-a-kind individuals
Watch Now
Documentary
The latest stories to watch.
Watch Now
Lifestyle
Inside the homes of millennial women — & what they paid for them
Watch Now
Comedy
Let's talk about sex, baby.
Watch Now
Documentary
Female artisans around the world
Watch Now
Politics
Made by and for smart, opinionated women.
Watch Now
Film
We helped 12 female directors claim their power.