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Fashion

The Best Outfits From The Final Season of Insecure

Looking back on our favorite characters and their most memorable outfits.

HBO’s hit series Insecure just wrapped up its fifth and final season, giving us not only some much-needed closure and the fate of the beloved characters, but also showcasing their inspiring growth that will be dearly missed.

First airing back in 2016, the trailblazing “dramedy” quickly became a fan-favorite worldwide with its authentic storylines of the Black experience in Los Angeles and introducing its viewers with underrated gems in its music soundtrack. Above all, we can’t forget how the show captivated the audience with such coveted and groundbreaking fashion moments in every episode, curated by none other than stylist and costume designer Shiona Turini.

#InsecureSundays are no more, with the series finale just airing on Sunday, Dec. 26, but we can definitely say that last season brought us perhaps the best outfits of the show. Look back at some of our favorite fashion takes that we absolutely adored throughout Season Five of Insecure, below.

Warning: Spoilers for Insecure ahead.

Ep. 1: "Reunited, Okay?!"

HBO Max screenshot

HBO Max screenshot

In the very first scene of the new season, we’re greeted with a number of jaw-dropping looks from the characters. Issa is seen leaving the airport in a casual layered look. She wore a green and gray bomber jacket with wide-legged pants. She tied a flannel at the waist and finished her outfit with white sneakers.

HBO Max/Raymond Liu

While visiting their alma mater at Stanford, Issa donned a green ombré plaid set from Dries Van Noten and also debuted the new sage Telfar mini bag.

By her side, Molly opted for a cream-colored suiting look with a white clutch from Bottega Veneta.

HBO Max/Raymond Liu

Both Kelli and Tiffany also came into this season with looks for days! Tiffany rocked a pink and green belted dress by Gucci (which represented her AKA sorority), while Kelli wore a monogram denim and lace dress, also by Gucci.

HBO Max/Raymond Liu

Molly is known for her stunning monochrome ‘fits. In this scene, she wears an all-orange look from Sally LaPointe’s Pre Fall 2021 Collection.

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One of the funniest scenes from the season was when Molly and Issa were robbed by an old friend. While in a state of shock, Issa wore a short-sleeved tee from Online Ceramics with an orange skirt. Molly opted for an ‘80s zebra-printed one-shoulder dress by Patrick Kelly.

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And of course, we can’t forget that the robbers only wanted Molly’s dazzling metallic heels from Amina Muaddi, while they kindly declined to take Issa’s pair of shoes.

Ep. 2: "Growth, Okay?!"

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In the second episode, Molly continues to give us outfit inspiration in this Dodo Bar Or black top with a chain halter, paired with matching black bottoms and a mini bag.

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Issa’s assistant Quoia also served some notable looks. In this scene, she wore a Song of Style long-sleeve top layered over a brown plaid tank. She then tucked it under a matching Song of Style mint green skirt.

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Issa’s fashion sense has undoubtedly shifted along with her character growth. While expanding her business, she donned a custom-dyed blue turtleneck sweater by Jonathan Simkhai, with a blazer and skirt set from Thebe Magugu.

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Wearing another statement suiting look, with a green cropped tank underneath.

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Molly wore another stunning monochrome look to the office: a blue blazer by Christopher John Rogers and a matching turtleneck from Hermès.

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While visiting her beau Nathan at the barbershop, Issa wore a multicolored striped top and asymmetrical skirt set from Peter Do.

Ep. 3: "Pressure, Okay?!"

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Lawrence also gave us some subtle designer looks this season. In this scene, he wore a black “Ami de Coeur” cardigan by AMI Paris over a blue tee and black bottoms, along with a Cartier watch.

HBO Max/Merie W. Wallace

We can’t forget to include KeKe Palmer, who guest-starred in the episode as Condola’s sister. She wore a white cutout tank tucked into black-and-red joggers.

Ep. 4: "Faulty, Okay?!"

HBO Max/Merie W. Wallace

During the crew’s beach day in Episode 4, Issa wore a bright orange one-shoulder tank and shorts set under a rainbow-striped cover-up and a Bonsai handbag by Simon Miller. Molly is seen in a black center cut-out tank by Rui tucked into an asymmetrical and mesh skirt, while Kelli opted for an all-blue looks, including a Hanifa halter swimsuit and light blue cover-up set.

Ep. 5: "Surviving, Okay?!"

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HBO Max screenshot

While visiting her mother in the hospital, Molly switches her skin-baring dress for something a bit more comfortable with Issa, which was actually a one-shoulder cutout gown by Brandon Maxwell.

HBO Max/Glen Wilson

While losing track of time (and Molly’s dog Flava Flav), Issa sported a beige deconstructed tracksuit by Adidas x Danielle Cathari, pairing her outfit with a white tank and brown heels.

Ep. 6: "Tired, Okay?!"

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Wearing a custom-made Nike patchwork top over a white tee and pleated lavender bottoms.

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In the same scene, Issa is also seen wearing a green-and-white plaid set from Rosie Assoulin, with a contrasting yellow plaid tie at the waist.

HBO Max/Merie W. Wallace

While out to get food, Issa wore a brown V-Neck sweater by Burberry, with golden logo earrings by Telfar.

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Kofi Siriboe also made a cameo appearance as fashion designer Crenshawn in the show. He wore many notable looks, especially this all-white ‘fit.

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Molly’s work ‘fits will definitely be missed. I mean, this black dress with an asymmetrical neckline was so simple yet so chic!

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During a staycation with her law firm, Molly confides in her coworker Taurean wearing a teal seatbelt dress by Peter Do.

Ep. 7: "Chillin', Okay?!"

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While prepping for a girls’ night in, Issa continues to serve us loungewear inspiration as she wore a plaid button-up by Fe Noel over a white cropped tank from Lionne Clothing and red shorts from Sorella Boutique.

HBO Max/Merie W. Wallace

Wearing a white asymmetrical tank from Kendra Duplantier and denim jeans.

HBO Max/Merie W. Wallace

Tiffany is seen sporting a casual look by Adidas x Wales Bonner.

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HBO Max screenshot

Kelli arrived at the gathering opting for a gray maxi dress from Zerina Akers’ Bar III collection, while Molly wore a lace-up denim set by Samaria Leah.

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Donning a silk printed maxi jacket by Misa Hylton over a black dress.

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HBO Max/Merie W. Wallace

In this scene, Kelli wore a black-and-white kimono and pants by Diarrablu, while Molly is seen in a white kimono by Torlowei with a matching bralette and shorts. We also see Issa in a yellow printed pajama set from Bephies Beauty Supply and lingerie by Savage X Fenty, and Tiffany in a pink feather slip dress by Anya Lust.

Ep. 8: "Choices, Okay?!"

HBO Max/Merie W. Wallace

Wearing a long-sleeve printed top made in collaboration with Genevieve Gaignard and checkered red-and-white skirt to an event hosted by none other than The Blocc.

HBO Max/Merie W. Wallace

Molly also arrived at the outdoor event in a sleeveless sage-colored bralette and leggings set from Dion Lee, paired under a matcha green button-up slouchy top and matching pants. Kelli’s striped blue number, including a Dior robe and Good American jeans, is also just as striking.

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Issa and Quoia speak to Crenshawn, with Issa rocking a dark green plaid look and Quioa in a mix-match patterned outfit.

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HBO Max screenshot

Issa visualizes her dream life with a hole-punched trench coat by Maison Margiela over a silk dress from Kendra Duplantier and heels.

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Issa’s alter ego looked just as stunning as she did (I wonder why!) In this scene, she wore a neutral-hued top and pants combo, which is adorned with black mesh on the sleeves.

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Wearing a fuchsia satin mini shirtdress by Attico.

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Opting for a red cutout top tucked into wide-legged light orange trousers, finishing off with a Brownie Twist signature necklace by The Brownies.

Ep. 9: "Out, Okay?!"

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While saying their goodbyes to Tiffany and Derek, Molly stunned in a vintage Ann Demulemesster black-and-white halter dress from Replika Vintage. By her side, Taurean is seen in a baby blue suit.

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Tiffany’s outfits throughout the show were unforgettable. At her farewell party, she wore a floral-print bustier top and matching skirt by Christopher John Rogers.

HBO Max/Merie W. Wallace
HBO Max/Merie W. Wallace

Issa wore a Jean Paul Gaultier orange silk mini dress from Replika Vintage along with a patchwork clutch while Nathan is seen in a striped button-up over a gray tee and black pants.

Ep. 10: "Everything Gonna Be, Okay?!"

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Wearing a black cutout top by Sid Neigum with denim jeans and pearl earrings from Completed Works.

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Quoia in this corset top by Miaou over a sparkling green dress was absolutely breathtaking!

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HBO Max screenshot

Molly comforts Issa after a rough break-up wearing a purple ribbed tank from Helmut Lang and white denim cutout pants by Maison Margiela.

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Tiffany shows her friends around her new home in a knitted coral red mini dress by Roberta Einer and a matching orange handbag from Coperni.

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In this scene, Issa wears a multicolored tie-dyed shirt from Celinewith a white bralette and nude leggings. On the left, Molly is rocking a mint green rib-knitted cardigan and flared trousers by Proenza Schouler.

HBO Max/Merie W. Wallace

Issa daydreams flying first-class with Ty Dolla Sign in a black-and-red floral-printed turtleneck by Dries Van Noten and matching red trousers.

HBO Max/Merie W. Wallace

Issa makes us never wanna go back to our solid-colored blazers after she was seen rocking this pink and plaid custom Balenciaga number.

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Kelli makes a special announcement in a silk green feathered dress, which was actually custom-made by the Insecure design team!

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Issa’s sparkly halter top and silk trousers also stood out in this scene.

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Molly looked absolutely stunning in her wedding, as she donned a white fern embroidered gown by Oscar de la Renta and custom heels from Brother Veilles. The groom looks just as dapper in his black-and-white tuxedo.

In one of the final scenes in the series, Molly’s bridesmaids are seen coordinating in red maxi ensembles by Valentino.

HBO Max/Raymond Liu

For many fans, this was quite a controversial happy ending, but nevertheless, we see Issa next to Lawrence and his son wearing a bright orange top and matching pants. Lawrence is also seen in a multicolored striped look.