Popsugar Fashion Fashion Shopping 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 8 September 2020 by Natasha Marsh Image Source: POPSUGAR Photography / Cindy-Lee Marsh As POPSUGAR editors, we independently select and write about stuff we love and think you'll like too. If you buy a product we have recommended, we may receive affiliate commission, which in turn supports our work. 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. Season 3: Cropped Sweatshirt and Jeans Image Source: HBO 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: POPSUGAR Photography / Cindy-Lee Marsh Truly, I could wear this outfit all day. It's so cosy. Madewell The Dad Jean in Millman Wash Image Source: madewell.com Madewell The Dad Jean in Millman Wash ($118) Madewell The Dad Jean in Millman Wash $118 from madewell.com Buy Now Mother Denim The Tomcat Jeans Image Source: motherdenim.com Mother Denim The Tomcat Jeans ($238) Mother Denim The Tomcat Jeans $238 from motherdenim.com Buy Now Alo Yoga Double Take Pullover Image Source: aloyoga.com Alo Yoga Double Take Pullover ($53) Alo Yoga Double Take Pullover $53 from aloyoga.com Buy Now Season 4: Biker Shorts and Sports Bra Image Source: HBO 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: POPSUGAR Photography / Cindy-Lee Marsh 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 Image Source: freepeople.com Lose Your Marbles Bra ($58) Lose Your Marbles Bike Shorts ($68) Lose Your Marbles Bra $58 from freepeople.com Buy Now Lose Your Marbles Bike Shorts $68 from freepeople.com Buy Now Girlfriend Collective Green Paloma Sports Bra and Bike Shorts Image Source: ssense.com Green Paloma Sports Bra ($50) and Green High-Rise Compressive Leggings ($75) Green Paloma Sports Bra $50 from ssense.com Buy Now Green High-Rise Compressive Leggings $75 from ssense.com Buy Now Season 2: The LBD Image Source: HBO 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: POPSUGAR Photography / Cindy-Lee Marsh 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 Image Source: whitehouseblackmarket.com Satin Strapless Sheath Dress ($90) Satin Strapless Sheath Dress $90 from whitehouseblackmarket.com Buy Now Gold Large Graduated Oval Chain Necklace Image Source: MISSOMA Gold Large Graduated Oval Chain Necklace($407) Gold Ridge Padlock Chain Necklace Image Source: missoma.com Gold Ridge Padlock Chain Necklace ($317) Gold Ridge Padlock Chain Necklace $317 from missoma.com Buy Now Season 4: Workwear Image Source: HBO 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: POPSUGAR Photography / Cindy-Lee Marsh I put together the same outfit vibe with a striped turtleneck and Lilka trousers. All Saints Exclusive Stripe Roll Neck Top Image Source: asos.com ALL SAINTS Exclusive Stripe Roll Neck Top ($46) ALL SAINTS Exclusive Stripe Roll Neck Top $46 from asos.com Buy Now Madewell Ribbed Turtleneck Top in Stripe Image Source: madewell.com Madewell Ribbed Turtleneck Top in Stripe ($20) Madewell Ribbed Turtleneck Top in Stripe $20 from madewell.com Buy Now Fashion ShoppingInsecureIssa RaeEditor ExperimentsScreen StyleMadewellMother DenimGirlfriend Collective