Popsugar Fashion Issa Rae Issa Rae's Best Outfits on Insecure Issa Rae Is the Queen of Casual Style on Insecure, and These Outfits Prove It September 16, 2021 by Nikita Charuza View On One Page Photo 23 of 37 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 23 Season 3 Styling a cropped sweater by Monse with high-waisted jeans. Previous Next Start Slideshow InsecureIssa RaeTVScreen Style