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.
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Molly's Turquoise Max Mara Suit
Remember when Molly breezes through the doorway at Andrew’s apartment in this monochromatic Max Mara number? Yeah, we can’t forget it either.
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Molly's Cozy Dinner Look
We wish Issa had gone in when she saw Molly through the window here, but there’s nothing we’d change about Molly’s outfit. The cosy, neutral knit and knee-high boots are perfect.
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Molly's All-White Vacation Style
When Molly touches down in Mexico for vacation with Andrew, they are taking in the view – but our eyes go straight to her Nanushka bodysuit and wide-leg pants. Oh, and that Christian Dior tote.
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Molly's Block-Party Jumpsuit
We knew Molly’s arrival at Issa’s block party would be dramatic, but we weren’t expecting this standout Staud jumpsuit, too.
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Molly's Denim on Denim
If only Molly and Issa’s friend date had gone a little better . . . but we have zero complaints about Molly’s denim-on-denim Iro outfit she wears for the occasion.
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Molly's Slick Print
For Issa’s mixer, Molly slips into this printed Sally LaPointe mini and totes a Balenciaga bag for a look that says “trendsetter” without even trying.
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Molly's Cutout Vacation Dress
Between the colour and the cutouts, this knit Cult Gaia dress is easily one of our all-time-favorite Molly looks.
HBO
Molly's Brilliant Date-Night Dress
Crafted with cutouts and in this statement-making citrus hue, Molly’s Dion Lee cocktail dress is easily one of the show’s most memorable looks. Just look at her glowing in this!
