Issa Rae’s beauty is far from insecure. Since 2011, she’s produced the HBO series Insecure, starred in a number of films, including as “President Barbie” in Barbie, and even launched a haircare line, Sienna Naturals. Much like her beauty on screen—her big barrel curls and purple lip in Barbie, for one—Rae’s red carpet and front row looks are just as confident as in her performances.
At the 2024 Fashion Awards, the doe-eyed actress and producer won the Pandora Leader of Change Award in an old Hollywood curl, extra-long lashes, and brown French tips (she favors an oval shape.) Her cheekbones, like at the Off-White Spring 2025 show, are lifted by her sweet smile often adorned with mocha glazed lips to match her powdered shadows.
At both the Vanity Fair Oscars Party and Alexandre Mattiussi SS 2025 show, Rae’s half-braided updo proved to be her signature. Meanwhile, slicked back buns are not far behind (as seen at the 75th Primetime Emmy Awards) which draw attention to her matte skin moments.
In honor of Issa Rae’s 40th birthday, take a look back at her best beauty moments in the recent past.
The Fashion Awards 2024
LONDON, ENGLAND – DECEMBER 02: Issa Rae, winner of The Pandora Leader of Change Award, poses backstage at The Fashion Awards 2024 presented by Pandora at Royal Albert Hall on December 2, 2024 in London, England. (Photo by Dave Benett/Getty Images)
2024 US Open
NEW YORK, NEW YORK – SEPTEMBER 07: Issa Rae attends the 2024 US Open at USTA Billie Jean King National Tennis Center on September 07, 2024 in New York City. (Photo by Marleen Moise/Getty Images)
Off-White RTW Spring 2025
Issa Rae at Off-White RTW Spring 2025 as part of New York Ready to Wear Fashion Week held at the Brooklyn Bridge Park on September 8, 2024 in New York, New York. (Photo by Gilbert Flores/WWD via Getty Images)
Alexandre Mattiussi Menswear Spring/Summer 2025
PARIS, FRANCE – JUNE 20: (EDITORIAL USE ONLY – For Non-Editorial use please seek approval from Fashion House) Issa Rae attends the AMI – Alexandre Mattiussi Menswear Spring/Summer 2025 show as part of Paris Fashion Week on June 20, 2024 in Paris, France. (Photo by Julien M. Hekimian/Getty Images)
2024 Vanity Fair Oscar Party
BEVERLY HILLS, CALIFORNIA – MARCH 10: Issa Rae attends the 2024 Vanity Fair Oscar Party Hosted By Radhika Jones at Wallis Annenberg Center for the Performing Arts on March 10, 2024 in Beverly Hills, California. (Photo by Daniele Venturelli/Getty Images)
96th Annual Academy Awards
HOLLYWOOD, CALIFORNIA – MARCH 10: Issa Rae attends the 96th Annual Academy Awards on March 10, 2024 in Hollywood, California. (Photo by Mike Coppola/Getty Images)
75th Primetime Emmy Awards
LOS ANGELES, CALIFORNIA – JANUARY 15: Issa Rae attends the 75th Primetime Emmy Awards at Peacock Theater on January 15, 2024 in Los Angeles, California. (Photo by Frazer Harrison/Getty Images)
Marni Womenswear Spring/Summer 2024 show
PARIS, FRANCE – SEPTEMBER 27: (EDITORIAL USE ONLY – For Non-Editorial use please seek approval from Fashion House) Issa Rae attends the Marni Womenswear Spring/Summer 2024 show as part of Paris Fashion Week on September 27, 2023 in Paris, France. (Photo by Pascal Le Segretain/Getty Images)
2023 photo call for Barbie
LOS ANGELES, CALIFORNIA – JUNE 25: Issa Rae attends the press junket and photo call For “Barbie” at Four Seasons Hotel Los Angeles at Beverly Hills on June 25, 2023 in Los Angeles, California. (Photo by Jon Kopaloff/Getty Images)
2023 photo call for Barbie
LONDON, ENGLAND – JULY 12: Issa Rae attends a photocall for “Barbie” at the London Eye on July 12, 2023 in London, England. (Photo by David M. Benett/Jed Cullen/Dave Benett/WireImage)
54th NAACP Image Awards
PASADENA, CALIFORNIA – FEBRUARY 25: Issa Rae attends the 54th NAACP Image Awards at Pasadena Civic Auditorium on February 25, 2023 in Pasadena, California. (Photo by Frazer Harrison/Getty Images)
29th Annual ELLE Women in Hollywood Celebration
LOS ANGELES, CALIFORNIA – OCTOBER 17: Issa Rae attends the 29th Annual ELLE Women in Hollywood Celebration on October 17, 2022 in Los Angeles, California. (Photo by Jon Kopaloff/WireImage,)
EBONY Power 100
LOS ANGELES, CALIFORNIA – OCTOBER 29: Issa Rae attends EBONY Power 100 at Milk Studios Los Angeles on October 29, 2022 in Los Angeles, California. (Photo by Leon Bennett/Getty Images for EBONY MEDIA GROUP)
So Phresh, So Clean! Source: Dia Dipasupil/Getty Images It’s absolutely necessary that we celebrate the ice cold brothers of Alpha Phi Alpha Fraternity, Inc. on their 119th year...
Courtesy of INNBEAUTY Before India Bradley stands en pointe to frame herself steadily to achieve a classic pirouette, or even prior to her wrapping on her ballet shoe,...
GloRilla is giving an update on where she stands with Young Thug now, after they previously traded words when his jail calls leaked. Thugger had everyone glued to...
Source: Paras Griffin / Getty Todd Tucker and Kandi Burruss’ divorce details are emerging, including Todd’s claim that he signed their prenup during their Bravo wedding special under...
Source: O2O Creative / Getty BOSSIP has covered thousands of stories of police brutality, misconduct, violence, and otherwise untoward behavior. We thought we had seen it all manners...
