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Issa Rae’s five major glow-up style moments that cemented the girl boss as a total fashionista

The Insecure creator celebrated her 36th birthday with a special surprise for fans.

issa rae
Brandi Fowler
Brandi FowlerFashion and Lifestyle Writer
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As Issa Rae celebrates her 36th birthday today, we are ringing in the Insecure creator and star’s big day with some of her most major style moments. 

In true girl boss fashion, Issa had a special surprise for fans Tuesday as they wished her happy birthday. She popped up on Instagram in a video, announcing that she would be teaching a MasterClass about how she broke into Hollywood - and how they can too. 

issa rae dress

Issa wore this dreamy green Michael Kors dress to the designer's 2020 fashion week show

“I’m so excited to share my @MasterClass with you all!,” she captioned the video. “I’m going to teach you everything I know about how I DIY’ed myself into Hollywood. I’ll teach you about how I build characters who look and feel like the people around me. We’re going to talk about finding your voice and your story; we’re going to talk pilot writing; we’re going to talk about how to build and grow with other creative people.”

She continued, “It doesn’t matter if you want to create a web series or a TV show or just a trendsetting dance move. If you feel like you only have one shot, you’re playing the game wrong. I hope you join me!” 

issa rae glam

Issa struck a fierce pose in this yellow Dion Lee dress at the 2019 Soul Train Awards

The Photograph star, who enjoyed an early birthday celebration with friends on a yacht, has come a long way since her Youtube series Awkward Black Girl catapulted her into superstardom - and she’s blossomed into a trendsetting style star. 

Issa’s style is versatile, she takes risks that pay off, and even when she’s rocking sky-high stilettos, a gown with intricate beading, or a mini dress with delicate ruffles, she makes it look effortless (and really good). We also love that she makes it a point to rock natural hairstyles with nearly every look.

Take a peek at five of Issa's five major glow-up style moments that cemented the girl boss as a total fashionista.

Issa’s 2019 Essence spread 

Issa stunned in so many looks on her April 2019 Essence cover and spread, but the neon green ruffled Marc Jacobs dress she wore in this shot was one of our faves. 

Issa’s Pandemic Emmy Dress 

issa rae emmys dress

The actress made the most of her Emmy nomination in spite of the pandemic, popping up in her private celebration in this gorgeous, structured orange Sergio Hudson dress that came complete with a cut-out.

A major dress at The Little Premiere

issa rae black dress

Issa stunned when she stepped out on the red carpet of the premiere of Little wearing a sculptural, sequined black Balmain mini dress that had a plunging neckline. 

Issa covers Billboard

Rocking the perfect cozy fall ensemble, Issa slayed as she strutted down the street in this orange Christian Wijnants sweater and skirt paired with chunky Giuseppe Zanotti red heels. 

Rocking the Carpet

issa rae style

Issa made a major style statement when she wore this sheer white Leilou by Aleksandra Dojcinovic dress with a beaded black neckline to the Black Girls Rock! in 2017. 

With a new Insecure season in the works and more projects on the way, we can't wait to see what's in store for this birthday girl this year - and the new ways she makes a style statement.

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