For five glorious seasons, “Insecure” punctuated our Sunday nights, social media feeds and group chats. The life, loves and friendships of Issa Dee and her crew of young, ambitious and thriving Black women became a part of the zeitgeist, and all of our lives feel just a bit emptier knowing their stories have reached their conclusion (as far as we’ve seen) when the HBO series’ finale aired on December 26th. We’ve evolved with these characters over the years — through their relationship failures, career milestones and all-around hijinks that made us laugh, cry, scream and every other human emotion we could conjure up. Their personal development wasn’t always linear, which made their journeys feel all the more real. What remained a constant, though, was how fashion reflected and progressed each character’s narrative.
Like the music in the series, the wardrobe seen on screen showcased up-and-coming Black creators, an effort spearheaded by “Insecure” co-creator and star Issa Rae and costume designers Ayanna James and Shiona Turini. For five seasons, these smaller labels effortlessly played alongside household names like Gucci and Oscar de la Renta, becoming known all over the world themselves thanks to the power of the show and social media. (Each character’s looks were quickly identified and tagged post-episode airing.) It’s a synergy that quickly became a part of the show’s legacy, right along with its plotlines, character development and backdrop of southern Los Angeles.
“‘Insecure’ has created a strong movement centering Blackness on television, from Black experiences to Black characters to Black love to Black elegance, in such a relatable way that was not done before,” says Diarrablu designer Diarra Bousso. “It’s easy to identify with them, and as a result, it’s also easy to see oneself in their style. ‘Insecure’ is basically telling the Black community: ‘Everything about you, your style, your Blackness, is so dope.'”
Bousso’s brand appeared on the final season of “Insecure,” worn by the beloved Kelli Prenny (played by the brilliant Natasha Rothwell). After the accountant-slash-podcaster was spotted in a Diarrablu robe and pants set, the brand saw an increased demand for the already-bestselling styles.
Kelli (Natasha Rothwell, far right) wearing Diarrablu on “Insecure” season five, episode seven.
Photo: Merie Wallace/HBO
According to Bousso, Diarrablu’s Instagram reach was also the highest it’s ever been over that entire month and got a repost from Amanda Seales, who played Tiffany on the show. Another important development to come out of the outfit credit: “We got some requests from other television shows right away for our kimonos and headwraps in various prints.” It was a super proud moment overall, with tons of DMs from Diarrablu fans.
“I think ‘Insecure’ was the first time in a long time Black brands were prioritized while still cementing each character’s personal fashion identity,” says stylist and content creator Kelly Augustine. “Shiona Turini’s work will forever be immortalized in these characters. I think the success of many of the Black brands and artists showcased encouraged other shows — and not just Black-centered media — to include Black designers into the fold. There has been success in abundance since 2020 for so many of our favorites.” (Some of her favorite fashion moments from the series include Kelli’s blue swim outfit for the beach party and Issa’s flash-forward looks, both from season five, and Lawrence’s Best Buy polo.)
K.ngsley designer Kingsley Gbadegesin likens the cultural impact of the fashion on ‘Insecure’ to that of ‘Sex and the City,’ noting how having his designs on the series gave his brand major visibility — necessary for a line that launched just a little over a year ago.
“My tank was in the infamous scene where Issa asks Nathan to spend the night,” Gbadegesin says. “Sharing the news on my social media was like wildfire, and I was able to see immediate sales from the exposure. It was also great to see people who knew the brand be just as excited and tag us in their stories on social media when they saw the scene. It felt like it was not just a K.ngsley thing, but an us thing.”
Seeing his designs on the small screen was pivotal for Gbadegesin personally — a once-in-a-lifetime opportunity, now that the series has come to an end. “As someone who’s watched the show since it aired and has followed the lives of these characters, to be cemented in their legacy was something beyond my wildest dreams,” he says. “Especially how it tied into the storytelling; the producers and Shiona did their thing for the final season.”
Victor Glemaud is also a huge “Insecure” fan. He watched from the very beginning, every Sunday — admittedly not something he does with any other show. “This series has been authentic and it has celebrated the culture,” he says. “It celebrates fashion, and all the characters are fully thought out in terms of their style. I think that will its fashion legacy, and the legacy of the whole show. It’s fun, smart, witty, sexy and real.”
Issa wearing a Victor Glemaud Resort ’20 set in season four, episode three.
Photo: Merie W. Wallace/HBO
It’s been great for his namesake brand to be featured several times on “Insecure” over the course of five seasons, as a small part in something that’s bigger than Glemaud or his label. “People truly remember the clothes,” he says. “For us designers, it takes a collection and brings it into reality.”
One particular moment stands out for him: a yellow and white-striped turtleneck and a chevron mini skirt from Resort ’20 (pictured above). “Shiona put a mustard yellow leather shirt over it from another brand,” he says. “After she reached out and ordered the look, I forgot about it because television takes so long to air. And when it did in season four, it wasn’t just about the look and how it was styled, but what the character of Issa Dee was doing and how that scene was filmed. It took the designs somewhere else that was beautifully visible, powerful and really exciting.”
It’s this kind of context and connection that these small Black-owned fashion brands want to continue seeing from costume designers, stylists and the fashion industry at large.
“Every single piece was designed by a Black woman in the ‘Insecure’ episode my designs were featured in,” says Bousso. “Can you imagine what it would be like if every television show did that for at least for one episode? It’s these small actions that can spark change in an industry where legacy brands have so much power and where there is little room for newbies. Supporting our work is a way to keep the conversation relevant and welcome innovation.”
Augustine has seen an uptick of Black designers used in a slew of other hit television series over the last year, including “Gossip Girl” and “And Just Like That,” and she wants costume designers to keep that same energy. Gbadegesin wishes the same, with the hope that stylists continue to advocate for Black talent and pass the torch.
“It’s nice to have access to the conglomerate brands, but there was something so amazing on being on a show like ‘Insecure’ and seeing my peers such as Aisling Camp, House of Aama and Honey Fucking Dijon showcased in such a way,” he says.
Glemaud believes that all great shows understand the impact of fashion, and he wants costume designers and those who work in television to learn from how “Insecure” approached its characters’ style.
“Fashion plays its own role, and that can be helped along by unknown brands, not just high-end luxury labels,” he says. “Smaller brands and vintage are important, as well. You can find something beautiful on The RealReal or in a store, just the same. Costume designers and stylists should go out there and explore new brands and designers.”
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