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

As the show's fifth and final season airs, we look back at the sartorial rise and rise of Issa Rae.


by Remy Farrell |

If you haven't already watched all five series of Issa Rae's comedy 'Insecure' on Sky Atlantic, don't panic, you still have time to add it to your watch list. It has been one of the most critically acclaimed and beloved fan series of the last three years (counting Tracee Ellis Ross and Rihanna as fans), and is the brainchild of one of Hollywood's most exciting rising stars, Issa Rae.

Rae, the show's writer, producer, and protagonist, began her career by writing and producing TV shorts, but officially made it big across the pond with the release of Insecure, a slick, sharp, and honest take on the lives of twenty something African-American women, navigating love and life in Los Angeles in a way that had rarely been shown on camera. But just as ground breaking as the shows script, was the costume design courtesy of stylist Shiona Turini.

Just as Sex and The City had it's clearly defined characters and their equally iconic looks, so too Shiona and Issa introduced a friendship group we could identify with, complete with visual cues. After all, which friendship group doesn't have the larger than life comedian (in this case Kelli), who can always be counted on for a bold, graphic print a la Samantha Jones. Or, the career orientated Molly, who mixes office ready tailoring with fashion forward designer labels (think Miranda Hobbes, with a sexier edge). With each season as much as we were invested in the relationships and the heartbreak, we were just as keen to see what the characters would be wearing next, and none more so than Issa, who both on screen and off, was evolving in the style stakes.

From championing Black designers like Telfar, Christopher John Rogers, and Pyer Moss (episode seven of the series even focused solely on costumes designed by black women), the show manages push the boundaries of styling for the small screen, while also reflecting Issa's own personal style.

With season five marking the final chapter for the show, we see a big transformation in Issa's life goals, and with that a much more directional, professional wardrobe, something Shiona describes as a ‘levelling up’. And as we've watched the character grow over the last five years, so too have Issa's own red carpet and street style looks, taking cues from her onscreen persona and affirming herself as one to watch. Especially in July, when after a handful of low key appearances, Issa announced her secret marriage to long term partner Louis Diame in the most stylish way possible. A totally unexpected picture on Instagram, wearing a custom Vera Wang Chantilly lace gown that is just about as traditional and romantic as it gets.


So in honour of the shows finale, we take a look back at Issa's style journey over the last couple of years, while we wait with bated breath to see what she does next. Expect bold colours, power suits, and plenty of statement accessories.


SEE: Issa Rae's Best Looks

SEE: Issa Rae's Best Looks
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Small spoiler ahead, but it would be remiss to discuss the Insecure finale without mentioning these already unforgettable Valentino bridesmaid looks.

SEE: Issa Rae's Best Looks
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The formula to the autumn outfit that everyone was wearing? A knit + mini skirt = the perfect combo, but we understand swapping the cable knit for an Opening Ceremony mesh top when contending with the LA heat. (Oh, and if you missed the first drop of Telfar bags, as sported by Issa in this look from season 5, here's how to get your hands on some of the Telfar collab with Ugg).

SEE: Issa Rae's Best Looks
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Issa's casual looks in the show as just as memorable as her formal wear, and fans of this Adidas X Danielle Cathari tracksuit may have spotted the exact tracksuit on ASOS.

SEE: Issa Rae's Best Looks
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We spotted a corset look from Central St Martin's alumni Charlotte Knowles in the first episode of series 5, setting the tone for the very stylish series ahead.

SEE: Issa Rae's Best Looks
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Issa was green carpet ready in a Rokh dress from the SS22 collection back in October, and somehow a halterneck, cut out, and ostrich feather trim made total sense?

SEE: Issa Rae's Best Looks
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Back in September, Issa wore a sculptural Congtri dress and Yun Yun Sung Earrings on the cover of Self Magazine. A lesson in how to do cool, contemporary partywear if ever we have seen one.

SEE: Issa Rae's Best Looks
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Issa's custom Vera Wang wedding gown was a sweetheart necklined ballroom gown, detailed with hand-placed Chantilly lace and hand-sewn crystal beading.

SEE: Issa Rae's Best Looks
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Proving diamonds are a girls best friend, Stylist and Costume Designer Shiona Turini paired a Cartier choker with a Givenchy suit for Issa's first Hollywood Reporter cover, and we are sold on Issa's penchant for a modern suit.

SEE: Issa Rae's Best Looks
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If you needed any further proof that David Koma is having a moment, Issa and stylist Jason Rembert opted for a neon number for her SNL promo shoot.

SEE: Issa Rae's Best Looks
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As Issa navigated her rocky relationship with Lawrence in series 4 of Insecure, could the ultimate power move be opting for a power blazer when reconnecting with an ex for the first time?

SEE: Issa Rae's Best Looks
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Answering the age old question "how do I wear black in summer?" If Issa's Brandon Maxwell two-piece isn't a viable option, we might just settle for an inspired high-waisted maxi skirt instead.

SEE: Issa Rae's Best Looks
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From Public Enemy to NWA, De La Soul to Fela Kuti's 'War can never be the answer', Issa's slogan t-shirts became a way to make political statements throughout the show.

SEE: Issa Rae's Best Looks
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Let's face it, suits never go out of style. And after 2021 became the year of the mini skirt, we're optimistic that a skirt suit revival is well overdue.

SEE: Issa Rae's Best Looks
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Sunshine yellow! Proenza Schouler! There is nothing not to love about this joyful pop of colour that is quite literally a shot of visual dopamine.

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And once again showing how to make tailoring less stuffy and more stylish, Issa's choice of a Vera Wang suit for New York Fashion Week showed a refined side to her otherwise colourful wardrobe.

SEE: Issa Rae's Best Looks
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Give your entrance maximum impact with minimal fuss in a head to toe colour like Issa's block red.

SEE: Issa Rae's Best Looks
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Never one to shy away from colour, this simple but elegant dress is a masterclass in pairing jewel tones and skin tone.

SEE: Issa Rae's Best Looks
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Issa's first Met Gala look combined the year's theme 'Heavenly Bodies' and cultural references to make a look all her own. Pairing references to ornate catholic iconography with 1988 movie Coming to America, the gown designed by Michael Kors reaffirmed Issa as one to watch.

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