Insecure [1] 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 [2], 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 [3] 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 [4] in the Black community and postpartum depression [5] 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 [6]. 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 [7] (thank God!), but if you find yourself desperate for more, scroll through and try some of the looks while you wait.
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.
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 [8] ($118)
Mother Denim The Tomcat Jeans
Mother Denim The Tomcat Jeans [9] ($238)
Alo Yoga Double Take Pullover
Alo Yoga Double Take Pullover [10] ($53)
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.
I picked up this set from Free People [11] 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 [12] ($58)
Lose Your Marbles Bike Shorts [13] ($68)
Girlfriend Collective Green Paloma Sports Bra and Bike Shorts
Green Paloma Sports Bra [14] ($50) and Green High-Rise Compressive Leggings [15] ($75)
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.
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 [16] 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 [17].
Satin Strapless Sheath Dress
Satin Strapless Sheath Dress [18] ($90)
Gold Large Graduated Oval Chain Necklace
Gold Large Graduated Oval Chain Necklace [19]($407)
Gold Ridge Padlock Chain Necklace
Gold Ridge Padlock Chain Necklace [20] ($317)
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.
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 [21] ($46)
Madewell Ribbed Turtleneck Top in Stripe
Madewell Ribbed Turtleneck Top in Stripe [22] ($20)