Home Fashion Styles Issa Rae’s Style Evolution: Her Most Memorable Outfits From ‘Insecure’ And Beyond

Issa Rae’s Style Evolution: Her Most Memorable Outfits From ‘Insecure’ And Beyond


You still have time to watch all five series of Issa’s comedy “Insecure” on Sky Atlantic. It has been a fan favorite and critically acclaimed series for the last three years, with Tracee Ellis Ros and Rihanna being fans. It was created by one of Hollywood’s most exciting rising stars, Issa.

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Rae, the show’s writer, producer and protagonist, started her career writing and producing TV shorts. However, Insecure was her first big success. It was a sharp, honest and slick take on the lives and experiences of twenty-something African American women. They navigate love and their lives in Los Angeles in a way rarely seen on film. The show’s costume design was just as groundbreaking, thanks to stylist. Shiona Turini.

Just like Sex and The City had its clearly defined characters and equally iconic looks. Shiona and Issa also introduced a friendship club we could identify, complete with visual cues. Kelli, the larger-than-life comedian, can always be relied upon for bold, graphic prints a la Samantha Jones. Molly, a career-oriented Molly, mixes office-ready tailoring with fashion-forward designer labels (think Miranda Hobbes with a sexier edge). We were as invested in the relationships and heartbreaks each season as we were in the characters. However, we were equally as interested in what the characters would wear next. Issa was no exception. She was constantly changing in her style.

The show is a showcase for Black designers like Pyer Moss, Christopher John Rogers, Telfar and Christopher John Rogers. Episode seven even focused on black women’s clothing. It also shows Issa her personal style.

Season five is the last chapter of the show. We see a major transformation in Issa’s goals and a more professional wardrobe. Shiona describes it as a “professional wardrobe”. ‘levelling up’. We’ve seen the character’s growth over the past five year, as has Issa’s own red carpet style and street style looks. Issa takes cues form her onscreen persona and makes herself a watchable star. Issa made a bold statement in July when she announced her secret marriage with Louis Diame, after only a few low-key appearances. This is an unexpected Instagram photo. Issa is wearing a custom Vera Wang Chantilly Chantilly lace dress that is as romantic and traditional as it gets.

In honor of the show’s final, we take a look at Issa’s style journey over the past couple of years, while we await with eager anticipation to see her next steps. Expect bold colours, power suits and lots of statement accessories.

SEE: Issa Rae's Best Looks 1 of 18

We will not spoil the ending of Insecure, but it would be remiss not to mention these unforgettable Valentino bridesmaid looks.

SEE: Issa Rae's Best Looks 3 of 18

Issa’s casual looks at the show were just as memorable than her formal wear. Fans of the Adidas X Danielle Cathari tracksuit might have spotted the exact suit on Issa. ASOS.

SEE: Issa Rae's Best Looks 4 of 18

In the first episode of series 5, Charlotte Knowles, a Central St Martin’s alumna, wore a corset. This set the tone for the highly stylized series to come.

SEE: Issa Rae's Best Looks 5 out of 18

Issa was dressed in a Rokh gown from the SS22 collection in October. A halterneck, cut-out, and ostrich feather trim made complete sense.

SEE: Issa Rae's Best Looks 6 of 18

Issa wore a Congtri dress with Yun Yun Sung earrings on the cover of Self Magazine in September. This is a lesson in how cool and contemporary partywear should be done, if we have ever seen one.

SEE: Issa Rae's Best Looks 7 of 18

Issa’s custom Vera Wang wedding dress was a sweetheart neckline ballroom gown with Chantilly lace, hand-sewn crystal beads and hand-placed Chantilly Lace.

SEE: Issa Rae's Best Looks 8 of 18


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Shiona Turini, Stylist and Costume Design, paired a Cartier necklace with a Givenchy suit to cover Issa’s Hollywood Reporter debut. This proved that diamonds are a girl’s best friend.

SEE: Issa Rae's Best Looks 9 out of 18

Issa and Jason Rembert chose neon colors for her SNL promo shoot, as if to prove that David Koma is in a moment.

SEE: Issa Rae's Best Looks 10 of 18

Insecure series 4 saw Issa navigate her difficult relationship with Lawrence. Could the ultimate power move be to opt for a powerblazer when reuniting with an ex?

SEE: Issa Rae's Best Looks 11 of 18

Answering the age-old question “how do I wear black in summer?”If Issa’s Brandon Maxwell 2-piece isn’t an option, we might settle for an inspired high waisted maxi skirt instead.

SEE: Issa Rae's Best Looks 12 of 18

Public Enemy, NWA, De La Soul, and Fela Kuti’s War can never be an answer’, Issa’s slogan tee shirts were a way to make political statements throughout their show.

SEE: Issa Rae's Best Looks 14 of 18

Sunshine yellow Proenza Schouler! This cheerful pop of colour is an instant shot of visual dopamine.

SEE: Issa Rae's Best Looks 15 of 18

Issa chose a Vera Wang suit to attend New York Fashion Week, once again proving how tailoring can be more elegant and less stuffy.

SEE: Issa Rae's Best Looks 16 of 18

Make your entrance stand out with minimal fuss and a head-to-toe colour like Issa’s block red.

SEE: Issa Rae's Best Looks 17 of 18

This simple, elegant dress is a masterclass on pairing jewel tones with skin tones.

SEE: Issa Rae's Best Looks 18 of 18

Issa’s Met Gala debut look combined the year’s theme ‘Heavenly Bodies’ with cultural references to create a look all hers. Michael Kors designed the gown that reaffirmed Issa’s status of a star by combining references to the 1988 movie Coming to America with ornate catholic iconography.

READ MORE: Who were the Best Dressed Stars of 2021?

READ MORE: Bennifer is Officially Reunited. Take a Look Back at Some of JLo’s Best Style Moments

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