Between dressing up for the office, dates around LA, and just hanging with Issa, Molly, played by Yvonne Orji, nails a cool-cum-sophisticated aesthetic season after season on HBO's Insecure. That's all thanks to the thoughtful styling of Shiona Turini, who took the reins as the show's costume designer in season three. With Shiona running the wardrobe department, Molly's looks became increasingly contemporary and fashion forward - without being overrun by trends. Shiona tapped Black designers, outfitting Molly in the likes of Cushnie and Off-White, as well as younger labels like Sally LaPointe, Cult Gaia, and The Attico, making each of Molly's onscreen appearances rife with memorable, covetable pieces. In that way, season four may be Molly's best collection of looks to date, making it exceptionally hard to choose favorites. Still, we tried. Here, as we gear up for season five (premiering on Oct. 24!), we're ranking Molly's eight best outfits from last season.