Paul Archuleta/FilmMagic/Getty Images

Fashion

Issa Rae's Style Evolution Into A Hollywood Leading Lady

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

by Erika Harwood

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.

Roger Kisby/Getty Images Entertainment/Getty Images
2014, SXSW Festival

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

Frederick M. Brown/Getty Images Entertainment/Getty Images
2016, HBO Post-Emmys party

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

Allen Berezovsky/Getty Images Entertainment/Getty Images
2016, Insecure premiere

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

George Pimentel/WireImage/Getty Images
2017, Golden Globes

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

Earl Gibson III/Getty Images Entertainment/Getty Images
2017, NAACP Image Awards

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

Amanda Edwards/Getty Images Entertainment/Getty Images
2017, Essence Black Women In Hollywood Awards Gala

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

Jason LaVeris/FilmMagic/Getty Images
2017, MTV Movie & TV Awards

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

Maury Phillips/Getty Images Entertainment/Getty Images
2017, BET Awards

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

Dia Dipasupil/Getty Images Entertainment/Getty Images
2017, Black Girls Rock!

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

John Shearer/WireImage/Getty Images
2017, Emmys

Wearing a red Vera Wang gown to the 2017 Emmys.

Frazer Harrison/Getty Images Entertainment/Getty Images
2018, Golden Globes

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

Paras Griffin/Getty Images Entertainment/Getty Images
2018, NAACP Image Awards

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

Jean Baptiste Lacroix/WireImage/Getty Images
2018, Black Panther premiere

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

Presley Ann/Patrick McMullan/Getty Images
2018, A Wrinkle In Time premiere

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

Jamie McCarthy/Getty Images Entertainment/Getty Images
2018, Met Gala

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

Dimitrios Kambouris/Getty Images Entertainment/Getty Images
2018, CFDA Awards

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

George Pimentel/Getty Images Entertainment/Getty Images
2018, Toronto International Film Festival

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

Axelle/Bauer-Griffin/FilmMagic/Getty Images
2018, Emmys

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

Taylor Hill/Getty Images Entertainment/Getty Images
2019, Critics' Choice Awards

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

Emma McIntyre/Getty Images Entertainment/Getty Images
2019, Little premiere

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

Gary Gershoff/WireImage/Getty Images
2019, Webby Awards

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

Michael Kovac/Getty Images Entertainment/Getty Images
2019, NBA Awards

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

Gilbert Carrasquillo/Getty Images Entertainment/Getty Images
2019, Black Girls Rock!

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

Leon Bennett/Getty Images Entertainment/Getty Images
2019, Soul Train Awards

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

Steven Ferdman/Getty Images Entertainment/Getty Images
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.

More from NYLON

Normani’s Style Evolution, From Girl Group Star To Solo Icon
By Jacquelyn Greenfield
Tierra Whack’s Style Evolution Into A Fearless Red Carpet Star
By India Roby