Breaking Down the Fashion on Insecure

Issa, Molly, Kelli, Condola and Lawrence
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Costumes on shows can tell the time the show was set in without the characters speaking! Costumes tell the story of the character’s lifestyle, socio-economic background, and even their diet choices. The same can be said about the popular HBO series “Insecure” with it’s leading lady, Issa Rae.


There is nothing subdued in this show as Fashion takes a stand and every outfit choice is intentional and tells it’s own story. Messages on T-shirts are pointed towards current Political issues and in this show the Black Hero doesn’t wear a cape, they wear curated outfits. Today, we will be breaking down the Fashions of a few characters on Insecure.

The Women of the Show

Issa Dee is the lead character in the show who was a 20 something (In Season 1) navigating her sometimes complicated life in L.A as she muddles through relationships, work, friendships, and everything else in between. Issa is pro-black and all about her natural hair and strong outfits for which she is famous for T-shirts and many Acid- wash Jeans and colorful tops that pay homage to the 90s. This was the era of cool, young black, successful people like “ Whitley” on a Different World, all the characters on “Living Single” and of course Will Smith and his Neon colors in the “Fresh Prince of Bel-Air”.

Issa Dee

Issa’s style boldly channels politics and pop culture. She wears a shirt that reads “forever my lady” with the former first lady Michelle Obama’s face on it (a Melody Ehsani design), as well as one that says “FBI Killed Fred Hampton,” a reference to the Black Panther leader who was assassinated in 1969, and another that pairs a no-nonsense image of Nina Simone with the word “MOOD.”– New York Times. As the seasons progressed, so did her style as she had to grow up and look more like an Entrepreneur. Here she mixes her Eclectic Tees with Blazers and de-constructed suits and complimented with her hair and natural tone make-up. 



Issa’s occasional bestie Molly, is the queen of monochrome! As a new partner at her firm, her outfits include tailored suits. When she is off the clock, her fits include matching workout gear and her other “casual wear” is still structured but features the latest runway looks that are carefully matched to make her stand out as the “young successful Lawyer”.  

Her outfit choices are based on the situation and or event and with her new role as a partner at her firm, we also see her with a short bob with beachy waves. Molly’s hair is a testament to where she is in life as a Bob is usually worn by more mature women who are professional yet still have a love of hair and all the various trends.


Kelli is a fun character and can be deemed as everyone’s ultimate “friend in my head”. She is an Accountant by day and Podcaster + seasoned troublemaker by night. Her personality is bold and fun with no filter and is always down for a good ole time.  She is always down for whatever, whenever and her style is a true reflection of this. Think of her as the loud yet successful Millennial who is often Issa’s Business Advice confidant who reminds her that she is “broke” and should do more to earn more.

She is styled in prints and surprisingly, she is one of the characters known for her accessories! She often wears statement earrings, fun necklaces, and earrings. Kelli loves a good bomber jacket, kimono or Co-ord set, and of course bold prints and bright colors.



She is the new girl on the show in Season 4 and comes on as Issa’s PR Executive and also Lawrence’s new bae! We know this pairing might be odd but it shows how realistic the situations are to real life and sometimes the person helping you to reach your goal might be your Ex’s, new bae. She is also a fellow naturalista and is great at her job as we see Issa’s idea taking fruition. 

Condola’s style is that of a person working in the Creative Industries and has a fun, fresh, and sometimes eclectic style. Her outfits are tailored (like Molly’s) but have an edge

Lead Male Character


Lawrence’s character on the show in my opinion has seen the most growth (other than Issa) and this is reflected in his style. He went from #thatdude who went from the signature Best Buy Blue Polo Shirts and Khakis to button-down Professional who wears more expensive and stylish Polo Shirts who now works in tech as Silicon Valley.

Who is your favorite character on the show and whose style do you identify with the most? Tell us in the comments below!

#Breaking Down the Fashion on Insecure

#Breaking Down the Fashion on Insecure

#Breaking Down the Fashion on Insecure

#Breaking Down the Fashion on Insecure

#Breaking Down the Fashion on Insecure


Haute People was launched in September 2011 as a Fashion Blog and has grown into a Lifestyle Blog. The Term “Haute” can be defined as “Fashionably Elegant” or of High Quality. This blog looks at topics from Beauty, Fashion, Entertainment, Hair Trends, Pop Culture as well as exciting new features every month. A favorite among our readers is “Behind The Seams” where influential people from the Creative Industries are featured. . Haute People are Smart, Bold, Creative and Individualistic. If you have an innate passion for Lifestyle, Fashion and all things current, you are HAUTE.

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