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How to Dress Like Issa From Insecure

I'm Losing My Mind Waiting For Insecure Season 5, So I Dressed Up as Issa All Week To Get My Fix

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Insecure first aired in 2016 and I began watching it in 2018. Although I was a late to the movement, I cannot get enough of this show! From the soundtrack to the important Black culture conversations that take place on Insecure, watching Issa and the rest of the crew always brings a smile to my face. Each season I find myself downloading majority of the soundtracks, grinning happily at Issa's latest love interest, and yelling in celebration for the light shed on gentrification, Black love and friendship.

Anxiously awaiting season four with the rest of the world, I couldn't have been more pleased with how well it was written, directed and outfitted. Season four had me doubting my loyalty to Lawrence while rooting for the underdog, Nathan. This season depicted mental health in the Black community and postpartum depression so beautifully. It showed Inglewood — a city just 35 miles from where I grew up - in all it's glory: the emphasis on local speciality, Randy's donuts; trendy Black-owned coffee shop, Hilltop; the night scene at Highland Park Bowl; and the dozens of references to Market Street.

But what I was really in awe of this season, was the fashion - specifically from Issa. We saw her evolve from previous seasons where her style took a backseat, to owning her glow and showing off her curves, thanks to the careful wardrobe curation by costume designer Shiona Turini. It was so powerful to see her character develop — and her clothing to match. Because I miss the show so dearly, I dressed up as Issa for a full week to get my fix. I know Insecure has been renewed for a fifth season (thank God!), but if you find yourself desperate for more, scroll through and try some of the looks while you wait.

Image Source: POPSUGAR Photography / Cindy-Lee Marsh

Season 3: Cropped Sweatshirt and Jeans

The fitted jeans and the movement in the top gives this outfit an instant polished chill vibe, which is something I'm always going for.

Image Source: HBO

Truly, I could wear this outfit all day. It's so cosy.

Madewell The Dad Jean in Millman Wash

Madewell The Dad Jean in Millman Wash ($118)


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Madewell The Dad Jean in Millman Wash
$118
from madewell.com
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Mother Denim The Tomcat Jeans

Mother Denim The Tomcat Jeans ($238)

Image Source: motherdenim.com
Mother Denim The Tomcat Jeans
$238
from motherdenim.com
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Alo Yoga Double Take Pullover

Alo Yoga Double Take Pullover ($53)

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Alo Yoga Double Take Pullover
$53
from aloyoga.com
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Season 4: Biker Shorts and Sports Bra

The season finale of Insecure aired on June 14th, and I'm still thinking about this yellow number. I love how this season placed emphasis on Self Care Sunday, where Molly and Issa would get together most Sundays and either have a yoga season or hike. Issa's outfits were so well-styled and seemed moveable enough that she could actually work out in them.

Image Source: HBO

I picked up this set from Free People and I love it! The pattern is so summery and the fabric is stretchy enough to withstand the hardest of workouts or just a morning at the farmer's market.

Lose Your Marbles Bra and Bike Shorts

Lose Your Marbles Bra ($58)

Lose Your Marbles Bike Shorts ($68)

Image Source: freepeople.com
Lose Your Marbles Bra
$58
from freepeople.com
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Lose Your Marbles Bike Shorts
$68
from freepeople.com
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Girlfriend Collective Green Paloma Sports Bra and Bike Shorts

Green Paloma Sports Bra ($50) and Green High-Rise Compressive Leggings ($75)

Image Source: ssense.com
Green Paloma Sports Bra
$50
from ssense.com
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Green High-Rise Compressive Leggings
$75
from ssense.com
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Season 2: The LBD

I love a good dress up moment and this LBD from season two perfectly compliments Issa's style. The cut outs of this dress are great for a night out or a dinner party.

Image Source: HBO

As much as I love dresses I'm always bothered when my straps fall. Because I have small shoulders, I tend to love strapless dresses and this one from White House Black Market is new to my closet but definitely a keeper. It's perfectly form fitting and is currently marked down for 50 percent off. When wearing a strapless dress I like to accentuate my open neck with stacked necklaces. Both of these gold platted on brass necklaces are from British brand, Missoma.

Satin Strapless Sheath Dress

Satin Strapless Sheath Dress ($90)

Satin Strapless Sheath Dress
$90
from whitehouseblackmarket.com
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Gold Large Graduated Oval Chain Necklace

Gold Large Graduated Oval Chain Necklace($407)

Image Source: MISSOMA

Gold Ridge Padlock Chain Necklace

Gold Ridge Padlock Chain Necklace ($317)

Image Source: missoma.com
Gold Ridge Padlock Chain Necklace
$317
from missoma.com
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Season 4: Workwear

Season four is where we started to see Issa channel some of Molly's professional work attire but with a quirky Issa spin on it. I love this outfit because it's a multiple-venue type of outfit. I could see myself it in for a girls brunch, work, drinks or an event.

Image Source: HBO

I put together the same outfit vibe with a striped turtleneck and Lilka trousers.

All Saints Exclusive Stripe Roll Neck Top

ALL SAINTS Exclusive Stripe Roll Neck Top ($46)

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ALL SAINTS Exclusive Stripe Roll Neck Top
$46
from asos.com
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Madewell Ribbed Turtleneck Top in Stripe

Madewell Ribbed Turtleneck Top in Stripe ($20)

Image Source: madewell.com
Madewell Ribbed Turtleneck Top in Stripe
$20
from madewell.com
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