Lipstick on the Rim How to Dress Like a Cool Mom: The Jeans, Sweaters & Capsule Staples Every Woman Needs
Dec 16, 2025
Join Cassidy Crockett, creator of the viral Cool Monologue series, as she unpacks the essence of 'cool mom' style, revealing essential outfit formulas and must-have staples. Discover her favorite denim brands like The Row and Re/Done and learn how to style key pieces like loafers and layered sweaters. Cassidy shares insights on winter trends, thoughtful color combos, and practical capsule wardrobes designed for busy moms. Plus, she reflects on her style icons and tips for rebuilding your wardrobe after life changes.
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How The Cool Mom Series Began
- Cassidy grew up watching stylish moms in Los Angeles and labeled that look 'cool moms'.
- She moved to New York, started documenting street style, and her 'Cool Mom' videos went viral.
Invest In Wearable Staples
- Buy high-quality staples you wear repeatedly like jeans, cashmere sweaters, and a great belt.
- Invest where you reach most: fit and material matter more than logos.
Effortless Is About Fit And Fabric
- A 'cool mom' look reads effortless because clothing fits well and uses good materials.
- The vibe is that you are wearing the outfit, not the outfit wearing you.