Insecure: Issa’s 10 Best Outfits


There are countless of reasons why you should watch HBO’s Insecure. Not only is it one of the rare shows that do representation right, it’s also endlessly aesthetically pleasing. Even without reading trivia, it is obvious that the show is essentially an ode to Los Angeles, showing the viewers there is much more to the City of Angels than Hollywood and Malibu. Bright scenery is accompanied by the main characters’ fashion choices. Despite being best friends, Issa and Molly both have their own distinctive styles.

Related: The 10 Best Outfits From The Umbrella Academy, Ranked

Issa loves vivid colors, patterns, prints, and casual T-shirts. She prioritizes comfort above everything else, but that doesn’t mean she only sports casual looks.

10 Issa Looking Great On Thanksgiving


In “Lowkey Thankful”, Issa wore a yellow jacket, a turtleneck top and a mini skirt, rocking the colors in which she looks her absolute best. Her brother came to the event looking unusually casual. Since their stepfather had to go to the hospital, the siblings ditched the rest of the family and decided to dine in a Mexican restaurant instead.

Issa’s looks were spot on, but her behavior wasn’t. Later on, she ditched Molly after their relationship was already rocky to begin with.

9 Orange Is Issa’s Go-To Color

insecure issa and molly

Molly typically doesn’t experiment with wild prints and vivid colors, but she has a presence that is much more intense than Issa’s. Issa on the other hand loves to wear earthy tones and playful patterns, plaid being one of the most common ones.

Just like Sex and the City tends to be unrealistic, Issa’s fashion choices don’t add up financially. She works part time as a building manager and drives Lyft, yet always looks as if she is a model. The series hints at what Issa does: she likes to buy clothes and return them after wearing them once to save money and to hide the fact that she is actually broke.

8 The Birthday Girl Outfit

issa's birthday party outfit wearing a striped jacket and a printed dress

Season 3 finale “Ghost-Like” commemorated Issa’s 30th birthday. Molly took Issa to see a public screening of The Last Dragon and, as the episode title suggests, the event was teeming with people from the past. Lawrence was there, being annoyingly sweet as ever, and even Jared was there: a guy that we all at some point thought Molly could end up with until she blew him off.

All four girls looked amazing in this episode, but Issa’s outfit definitely takes the cake. You’d think that wearing a striped jacket over a printed dress would be a bit much, but she pulled it off effortlessly.

7 Quitting Her Job Like A Boss

insecure issa wearing a yellow Out From Under tee with a graphic-print Dries Van Noten blazer in season 3

Issa worked at We Got Y’All for years and it didn’t seem like she was particularly enjoying it. By season 3, she was done with the organization since she was seriously underappreciated. When she decided to show Nathan around rather than go back to work one day, it was clear what needs to be done.

In one of the following days, Issa quit her job. It might have seemed like an impulsive decision to Frieda, but Issa must have known deep down that it was a long time coming. Her blazer meets jeans outfit mirrors her personality: she is all about being professional, but looking youthful at the same time.

6 Issa Serving Us Casual Looks

issa in a red top on insecure

Issa’s lace-up cropped sweater from Monse that Issa wore on “High-Like” is worth several hundred dollars, so it’s very likely that a girl like Issa couldn’t afford such items in real life.

She paired it with a pair of high rise jeans, prioritizing comfort above all else.

5 Hitting The Club With Daniel

issa and daniel king in the club on insecure

After being stuck in a complacent relationship with Lawrence for years, Issa glowed up whenever she was around Daniel. One night, they went out together because Daniel needed to network with a rising hip-hop star. The two made for a great couple and he is definitely the fan-favorite when it comes to guys that Issa should end up with.

Issa combined a jaw-dropping black top with a colorful mini skirt. No wonder strangers rushed to buy her drinks at the bar!

4 Overdressing For Her House Party

issa wearing a black dress on insecure

When Issa wanted to show Lawrence just how fine she was after the break up, she organized a casual get-together and wore a gorgeous black dress that was way too extra for a living room hangout. Even Molly showed up looking as casual as she can be, which only made Issa stand out more.

It was a comical and cringey situation. It’s a real shame Issa never wore the dress to an event that was actually worth it.

3 Issa’s Very Own Block Party Merch

issa and molly talk at the block party on insecure

Despite all the doubts, Issa threw her very own block party in Inglewood and it was a huge success – until the crowd scattered when it got late. The event was the central theme of season 4. For the big day, she decided to wear a blue plaid skirt, hoop earrings and the event’s official merch.

Related: Dollface: 5 Best Outfits (& 5 Worst)

She did what she does best: mixing a more formal piece of clothing with something laid-back and approachable. Way to go, Iss.

2 Beyoncé Or Bust: The Coachella Outfit

insecure girls on the pool party at coachella

When Issa woke up her girls, screaming one of her most iconic lines “Beyoncé or bust, bi***es!” on the morning of Coachella, we knew that they will all be dressed to the T for the occasion.

Related: The Mindy Project: Mindy’s 5 Best Outfits (& 5 Worst)

At first glance, Molly and Tiffany always come across as the most fashion-forward because they are the richest of the four and thus change up their looks more often, from head to toe. Issa’s style is much more practical. Her shorts easily take the cake as the best piece featured in the episode.

1 The Message Behind The Last Poets Top

issa wearing the last poets shirt on insecure

The coolest thing about Issa’s outfits is that she often raises socio-political awareness through the way she dresses. The Last Poets is a group of artists that dates back to the 1960s African-American civil rights movement. It’s an insight into what Issa is passionate about. She is definitely the biggest activist on the show.

Issa was also seen wearing a Lauren Hill t-shirt and a Biggie Smalls sweatshirt.

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Updated: October 25, 2020 — 12:00 am

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