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Four types of messages hidden behind issa’s shirts in Insecure

Who knew a 100% cotton tee could carry so much weight?

If you’ve watched Insecure, then you noticed that through the various ups, downs, and characters’ growth, one thing that remained consistent is Issa’s love for graphic tees. The garments with bold messaging appear at least once in every single episode. Believe me, this is not a mistake. It is a deliberate move by Insecure’s Costume Designer Ayanna Kimani to insert “Easter eggs”, as she refers to them, into the show. In a 25 minutes episode format, the tees serve as valuable insights into the character’s hobbies, interests, and political views without having to address them in the script.

Let us dive into the 4 types of messages behind Issa’s iconic graphic tee collection:

(Disclaimer : For this discussion, I will also include sweatshirts.)

 I love to see if the viewers catch my little Easter eggs. I love to see how they interpret the wardrobe. I like to see that they’re understanding it, and then everyone showing love to the show, that’s the coolest thing.”

AyannA kimani for


Off Duty, Issa continues to sport her iconic collection of tees which serve as a declaration of love for black culture.

Issa wearing Mary J Blige concert tee in season 3 
black culture easter egg
Images via HBO

In the comfort of her own home, we see Issa lounging in her Miseducation of Lauryn Hill shirt, Mary Blige and Prince concert tees. This is as a nice homage to music icons and in the process, we discover that Issa’s musical taste are unapologetically black. We can almost picture her “borrowing” the Prince tee from her parent’s closet or stumbling onto it in a vintage shop.

Issa wearing The Last Poest sweatshirt with orange flare pants at her friend gallery. Pensive look on her face
 (Credit: Lisa Rose/HBO)

At her friend’s art opening, she swaps her classic cotton tees – jeans combo for an elevated version of the casual look. We see her in a black The Last Poets sweatshirt paired with flared pants. For those who don’t know, founded in the late 60s, The Last Poets is a group of poets and musicians rooted in black nationalism and the civil rights movement. They are credited  as the forefathers of hip hop and have been featured in songs by the likes of Biggie and Common. This is proof that Issa’s knowledge in music history runs deep and, as a result, couldn’t feel more authentic.

Interestingly enough, their costume designers have mastered the dual use of graphic tees. A noteworthy look is the Nina Simone “Feeling Good” shirt which not only praises the legendary singer but depicts Issa’s feeling as she undergoes a big transition in her life. With newfound clarity in both her personal and professional life, she is feeling good… great even.

“Most of the time when Issa is chilling, you’ll see her in a hip-hop T-shirt. I did that in Season 2 a lot, and I would always put her in a T-shirt that interpreted her mood.

Ayanna Kimani in Observer
ISsa wearing Different word shirt in her apartment
Different World Tee | Image via HBO

Additionally, the show pays homage to the films and TV shows like Waiting to Exhale and Different World who have paved the way for a show like Insecure to exist today.  The nineties were an era where black sitcoms were produced in mass, and Different World laid the groundwork for next generation of sitcoms. Not only did the show portray multidimensional black characters, tackled politics but each character had their own distinctive style. Much like Insecure. Likewise Waiting to Exhale is a reference film in the black community. In today’s climate where living black is an act of resistance, where the pain of women of color is exploited for the big screen (cue the struggling single mother trope). Alas, seeing Issa, a multi-dimensional black woman living a regular life, embracing her favorite artists and shows is nothing short of refreshing. 

2. An opportunity to show love to her city

Issa at lunch table wearing SuperMall green hoodie with graphic in orange and yellow.
Images via HBO

What New York is to Carrie Brenshaw (Sex in the City), Los Angeles is to Issa.

L.A. culture is an integral part of the show. When it is not mentioned through the script, be prepared to see it injected in one of Issa’s outfits. In season 2, we see Issa at her favorite taco truck wearing a denim baseball vest with the word Inglewood printed in red. Inglewood is a City of Los Angeles County where Issa lives. A few episodes later, we see Issa wearing a purple Outkast shirt paired with yellow sweats. This ensemble pays homage to the East Coast 90s hip hop duo while the color pairing is a nod to the Los Angeles Lakers. Perhaps the most memorable “Easter eggs” are the Nipsey and Prince Tribute. With the passing of Nipsey coinciding with the filming of season 4, the show decided to incorporate his Marathon Clothing line into Issa’s wardrobe. My favorite is the SuperMall Green Hoodie with its retro aesthetic very much in tune with Issa’s love of vintage.

Issa running outside her The Dunes apartment . She is wearing purple outkast shirt with yellow baggy sweatpants
Images via HBO

3. Use as a political vehicle

Dubbed “conscious clothing”  by the  Costume Designer Ayanna Kimani .

T-shirts are also used to vehicle a political statement. Here, Hump shirt is making light of Donal Trump’s infamous slogan ” Make America Great Again”. Later, the show also revisits D.a.r.e, a failed anti-gang and drug program. One could interpret this as an invitation to push Issa outside her comfort zone. The most daring shirt is perhaps America’s Horror Story t-shirt by Inopportune Portrait, which features tiny Donald Trump figures. Interestingly, Issa wears it as she wakes up from a bad dream, anxiety-ridden after being ghosted by Nathan. Shot in 2016, perhaps this is a social commentary on America’s own political nightmare? One who, unlike Issa’s, they can’t seem to wake up from. Who knew a 100% cotton tee could carry so much weight?

Issa lying in bed wearing HUMP Make America Gyrate Again
Images via HBO

4. Tees are also a sign of oppression

But her tees can also be a symbol of feeling stuck. The “We got y’all ” t-shirt with its controversial image of a white hand holding three black children isn’t a symbol of comfort. It represents Issa’s workplace, where she feels stuck and not understood by her colleagues. The same place where after a fallout with Frieda, her only work friend, she wears a Public Enemy shirt, a direct representation of how she feels her colleague perceives her.

Zoom on Issa sweatshirt FBI killed Fred Hampton in public transportation
Images via HBO

As a matter of fact, t-shirts are used to illustrate tough messages such as the historical tensions between the FBI and black community through the “ FBI killed Fred Hampton” garment. While the sweatshirt worn by Issa on regular day to work is never mentioned in the storyline, the message is enough to raise a discussion between viewers. Not to mention the Trayvon hoodie worn by Molly on a girl’s night in as a tribute to the young victim of police brutality. What strikes me is the juxtaposition of heavy political messages with the normalcy of the characters who continues on their lives. Here fashion is used to show hard realities through the subtleties of clothes. It illustrates how black people navigate their days between microaggressions and traumatic experiences. Insecure doesn’t shove these hard messages down your throat, it has its characters wear them proudly on their chest and pushes you to reflect and investigate. And to you, I ask: what can be more authentic than a powerful message worn literally on one’s chest? That, my friend is how powerful fashion can be.

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