STYLE EVOLUTION

Issa Rae’s Style Glow-Up Has Only Gotten Bolder

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issa wearing fishnet dress
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When Insecure premiered five years ago, a force entered the entertainment stratosphere. As creator, writer, and star of the show, Issa Rae brought her cult fan base from her Awkward Black Girl Web series to the big leagues on HBO, and quickly became Hollywood’s latest darling, with a meteoritic rise to stardom. While her character onscreen may favor a casual look, Rae is not one to play it safe when it comes to the red carpet. Often opting for bold prints and statement-making heels, Rae changes up her look from occasion to occasion, and never shies away from a good jumpsuit. She’s also incorporated pieces by some major designers into her rotation, including a frilled Off-White dress at the 2017 MTV Movie & TV Awards, a custom Pyer Moss jumpsuit encrusted with 180,000 Swarovski crystals at the 2018 CFDA Awards (where she made history as the first Black female host), and an icy blue Cinderella-esque Vera Wang jumpsuit at the 70th Annual Emmy Awards. You could say that over the past five years Rae has had quite the style glow-up: The prints have gotten brighter, the patterns have gotten bolder, and it’s clear that she’s become a style star. In honor of the fifth and final season of Insecure, here’s a look back at her best red-carpet moments.

2021: Insecure Season 5 Premiere
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This caramel-colored feather cutout ensemble from Rokh was the perfect Insecure sendoff piece for Issa Rae, which she wore to the fifth and final season premiere.

2021: The Academy Museum of Motion Pictures Opening Gala
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Issa Rae wore a shimmering Alexandre Vauthier piece to the opening of The Academy Museum of Motion Pictures in September 2021.

2021: Emmy Awards
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Working with her stylist Jason Rembert, Issa Rae wore a silver fishnet dress from his Aliétte collection to the 2021 Emmy Awards.

2021: BET Awards
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Issa Rae showed up to the 2021 BET Awards meaning business in this white Balmain Spring 2021 blazer dress.

2020: Essence Black Women In Hollywood Awards Luncheon
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Issa Rae arrived to the Essence Black Women In Hollywood Awards Luncheon in this orange and pink Solace London Resort 2020 gown.

2020: AAFCA Awards
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Issa Rae wore a belted golden gown to the 2020 AAFCA Awards.

2019: Elle Women in Hollywood
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Issa Rae wore a yellow Ralph Lauren gown with a plunging neckline for the 26th annual Elle Women in Hollywood Celebration in 2019.

2019: NBA Awards
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Issa Rae wore a multicolored Peter Pilotto Fall 2019 gown to the 2019 NBA Awards in Los Angeles.

2019: Little Premiere
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Issa Rae arrives for the premiere of Universal Pictures’ Little on April 8, 2019, in Westwood, California.

2019: Beautycon Festival
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Issa Rae attends Beautycon Festival New York 2019 at Jacob Javits Center on April 06, 2019, in New York City.

2019: NAACP Image Awards
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Issa Rae attends the 50th NAACP Image Awards at Dolby Theatre on March 30, 2019, in Hollywood, California.

2019: Critics’ Choice Awards
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Issa Rae attends the 24th annual Critics’ Choice Awards at Barker Hangar on January 13, 2019, in Santa Monica, California.

2018: Emmy Awards
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Issa Rae attends the 70th Emmy Awards on September 17, 2018, in Los Angeles, California.

2018: Emmy Party
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Issa Rae attends the Audi pre-Emmy celebration at Kimpton La Peer Hotel on September 14, 2018, in West Hollywood, California.

2018: Rihanna’s 4th Annual Diamond Ball
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Issa Rae attends Rihanna’s 4th Annual Diamond Ball benefitting the Clara Lionel Foundation at Cipriani Wall Street on September 13, 2018, in New York City.

2018: The Hate U Give Premiere
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Issa Rae attends the The Hate U Give premiere during 2018 Toronto International Film Festival on September 7, 2018, in Toronto, Canada.

2018: HBO’s Insecure Live Wine Down
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Issa Rae poses for a photo during HBO’s Insecure Live Wine Down at Essence at the Ace Hotel on July 7, 2018, in New Orleans, Louisiana.

2018: CFDA
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Issa Rae attends the 2018 CFDA Fashion Awards at the Brooklyn Museum on June 4, 2018, in New York City.

2018: Met Gala
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Issa Rae attends Heavenly Bodies: Fashion & the Catholic Imagination, the 2018 Costume Institute Benefit, at Metropolitan Museum of Art on May 7, 2018, in New York City.

2018: Veuve Clicquot Fourth Annual Clicquot Carnaval
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Issa Rae at the Veuve Clicquot Fourth Annual Clicquot Carnaval Supporting the Pérez Art Museum Miami at Museum Park on March 10, 2018, in Miami, Florida.

2018: A Wrinkle In Time Premiere
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Issa Rae arrives at the premiere of Disney’s A Wrinkle In Time on February 26, 2018, in Los Angeles, California.

2018: Black Panther Premiere
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Issa Rae attends the premiere of Disney and Marvel’s Black Panther on January 29, 2018, in Hollywood, California.

2018: Image Makers Awards
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Issa Rae attends Marie Claire’s Third Annual Image Makers Awards on January 11, 2018, in West Hollywood, Los Angeles.

2018: Golden Globe Awards After Party
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Issa Rae attends HBO’s Official 2018 Golden Globe Awards After Party on January 7, 2018, in Los Angeles, California.

2018: Golden Globe Awards
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Issa Rae attends the 75th Annual Golden Globe Awards at the Beverly Hilton Hotel on January 7, 2018, in Beverly Hills, California.

2017: Wine Down With Issa Rae
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Issa Rae attends the Wine Down With Issa Rae event at Hollywood Roosevelt Hotel on November 18, 2017, in Hollywood, California.

2017: Emmy Awards
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Issa Rae arrives at the 69th Annual Primetime Emmy Awards at Microsoft Theater on September 17, 2017, in Los Angeles, California.

2017: 29Rooms
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Issa Rae attends the Refinery29 Third Annual 29Rooms: Turn It Into Art event on September 7, 2017, in Brooklyn.

2017: Black Girls Rock
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Honoree Issa Rae attends Black Girls Rock! 2017 at NJPAC on August 5, 2017, in Newark, New Jersey.

2017: ESPYS
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Issa Rae attends the 2017 ESPYS at Microsoft Theater on July 12, 2017, in Los Angeles, California.

2017: HBO Celebration
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Issa Rae attends the 20th Anniversary Celebration of HBO x ABFF at the Betsy Hotel on June 17, 2017, in Miami, Florida.

2017: American Black Film Festival Honors
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Issa Rae attends BET Presents the American Black Film Festival Honors on February 17, 2017, in Beverly Hills, California.

2017: BET Awards
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Issa Rae arrives at the 2017 BET Awards at Microsoft Theater on June 25, 2017, in Los Angeles, California.

2017: Film Independent Spirit Awards
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Issa Rae attends the 2017 Film Independent Spirit Awards sponsored by American Airlines at the Santa Monica Pier on February 25, 2017, in Santa Monica, California.

2017: MTV Movie and TV Awards
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Issa Rae attends the 2017 MTV Movie and TV Awards at the Shrine Auditorium on May 7, 2017, in Los Angeles, California.

2017: Essence Black Women in Hollywood
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Issa Rae at Essence Black Women in Hollywood Awards at the Beverly Wilshire Four Seasons Hotel on February 23, 2017, in Beverly Hills, California.

2017: NAACP Image Awards Dinner
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Issa Rae attends the 48th NAACP Image Awards Non-Televised Awards Dinner at the Pasadena Convention Center on February 10, 2017, in Pasadena, California.

2017: NAACP Image Awards
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Issa Rae attends the 48th NAACP Image Awards at Pasadena Civic Auditorium on February 11, 2017, in Pasadena, California.

2017: Golden Globe Awards
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Issa Rae attends the 74th Annual Golden Globe Awards at the Beverly Hilton Hotel on January 8, 2017, in Beverly Hills, California.

2017: Sundance
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Issa Rae attends the Power of Story: Art of Episodic Storytelling at Egyptian Theatre on January 26, 2017, in Park City, Utah.

2017: Golden Globe After Party
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Isaa Rae arrives at HBO’s Official Golden Globe Awards After Party at Circa 55 Restaurant on January 8, 2017, in Los Angeles, California.

2016: Women in Entertainment Breakfast
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Issa Rae attends The Hollywood Reporter’s Annual Women in Entertainment Breakfast in Los Angeles at Milk Studios on December 7, 2016, in Hollywood, California.

2016: Ebony Power 100 Gala
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Issa Rae arrives at the 2016 Ebony Power 100 Gala at the Beverly Hilton Hotel on December 1, 2016, in Beverly Hills, California.

2017: Film Independent Filmmaker Grant and Spirit Award Nominees Brunch
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Issa Rae attends the 2017 Film Independent Filmmaker Grant and Spirit Award Nominees Brunch at BOA Steakhouse on January 7, 2017, in West Hollywood, California.

2017: Golden Globe Party
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Issa Rae attends the Hollywood Foreign Press Association and InStyle’s Celebration of the 2017 Golden Globe Awards Season on November 10, 2016, in West Hollywood, California.

2016: Glamour Women of the Year
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Issa Rae backstage at the Glamour Women of the Year 2016 LIVE Summit at NeueHouse Hollywood on November 14, 2016, in Los Angeles, California.

2016: Emmy’s After Party
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Issa Rae attends HBO’s Official 2016 Emmy After Party at the Plaza at the Pacific Design Center on September 18, 2016, in Los Angeles, California.

2016: Insecure Premiere
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Issa Rae attends HBO’s Insecure Premiere at Nate Holden Performing Arts Center on October 6, 2016, in Los Angeles, California.

2016: Insecure Screening
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Issa Rae attends the 20th annual Urbanworld Film Festival Insecure Screening at AMC Empire 25 theater on September 23, 2016, in New York City.

2016: Visiting Sirius XM
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Issa Rae visits the SiriusXM Studio on October 3, 2016, in New York City.

2016: ESSENCE Black Women in Hollywood
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Issa Rae attends the 2016 ESSENCE Black Women in Hollywood awards luncheon at the Beverly Wilshire Four Seasons Hotel on February 25, 2016, in Beverly Hills, California.

2016: Insecure Screening
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Issa Rae attends 2016 BronzeLens Film Festival: HBO’s Insecure special screening at Georgia Pacific Auditorium on August 26, 2016, in Atlanta, Georgia.

2015: BET Awards Dinner
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Issa Rae attends the 2015 BET Awards Debra Lee Pre-Dinner at Sunset Tower Hotel on June 24, 2015, in Los Angeles, California.

2015: Love and Basketball Screening
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Issa Rae attends the Love and Basketball screening during the 2015 Los Angeles Film Festival at Regal Cinemas L.A. Live on June 13, 2015, in Los Angeles, California.

2014: People’s Ones to Watch
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Issa Rae attends People’s Ones to Watch event at the Line on October 9, 2014, in Los Angeles, California.