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.
Choose Denim That Flatters And Tailor It
- Try brands like The Row, AYR, Re/Done, and tailored Levi's for flattering denim.
- Tailor length and pocket placement to maximize fit and shape.
Winter Codes: Western, Collars, Camel
- Embrace Western touches, thick-collared sweaters, and camel tones for winter.
- Look for scarf-wrap or funnel coats and unique puffers to update outerwear.