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Fashion

Issa Rae's Style Evolution Into A Hollywood Leading Lady

A collection of the actor and writer's red carpet hits.

Issa Rae is a force both in front of and behind the camera, but she's also proven to be a can't-miss addition to the red carpet. In a handful of years, she's gone from simple trousers and blazers at SXSW to custom designer looks at awards shows. Check out her full style evolution ahead.

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2014, SXSW Festival

Wearing printed trousers and a red blazer to the South by Southwest festival in 2014.

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2016, HBO Post-Emmys party

Wearing a blue satin ruffled dress to HBO's Emmys party in 2016.

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2016, Insecure premiere

Wearing a red turtleneck dress to the premiere of Insecure in 2016.

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2017, Golden Globes

Wearing a white Christian Siriano gown to the 2017 Golden Globes.

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2017, NAACP Image Awards

Wearing a floral printed halter gown to the 2017 NAACP Image Awards.

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2017, Essence Black Women In Hollywood Awards Gala

Wearing a sheer black tulle gown to the 2017 Essence Black Women In Hollywood Awards Gala.

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2017, MTV Movie & TV Awards

Wearing a pleated Off-White dress to the 2017 MTV Movie & TV Awards.

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2017, BET Awards

Wearing a neon striped blazer and black shorts to the 2017 BET Awards.

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2017, Black Girls Rock!

Wearing a sheer white dress by Lei Lou to Black Girls Rock! in 2017.

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2017, Emmys

Wearing a red Vera Wang gown to the 2017 Emmys.

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2018, Golden Globes

Wearing a custom Prabal Gurung gown to the 2018 Golden Globes.

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2018, NAACP Image Awards

Wearing a sequined Marc Jacobs dress to the NAACP Image Awards in 2018.

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2018, Black Panther premiere

Wearing a white dress with ombré pleats by Rosie Assoulin to the 2018 premiere of Black Panther.

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2018, A Wrinkle In Time premiere

Wearing a gold Pyer Moss turtleneck gown to the premiere of A Wrinkle In Time premiere in 2018.

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2018, Met Gala

Wearing a black-and-gold Michael Kors collection gown to the 2018 Met Gala.

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2018, CFDA Awards

Wearing a sheer blue one-shoulder jumpsuit by Pyer Moss to host the CFDA Awards in 2018.

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2018, Toronto International Film Festival

Wearing a floral Oscar de la Renta gown to the Toronto International Film Festival in 2018.

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2018, Emmys

Wearing an embellished powder blue Vera Wang jumpsuit to the 2018 Emmys.

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2019, Critics' Choice Awards

Wearing a black gown by Aliétte to the 2019 Critics' Choice Awards.

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2019, Little premiere

Wearing a sequined puff-sleeve mini dress by Balmain to the premiere of Little in 2019.

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2019, Webby Awards

Wearing a low-cut cinched blue dress to the 2019 Webby Awards.

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2019, NBA Awards

Wearing a flowing Peter Pilotto dress to the 2019 NBA Awards.

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2019, Black Girls Rock!

Wearing a green turtleneck dress by Greta Constantine to Black Girls Rock! in 2019.

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2019, Soul Train Awards

Wearing a white cutout Dion Lee dress to the 2019 Soul Train Awards.

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2020, The Photograph premiere

Wearing a pale yellow Paule Ka dress to the premiere of The Photograph in 2020.

See more style evolutions from Florence Pugh, Kiernan Shipka, and Raven Symoné.

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