How to Dress Like a Cool Mom: The Jeans, Sweaters & Capsule Staples Every Woman Needs

Ever look at your closet and think, I have nothing to wear… even when it’s fully stocked? You’re not alone. We’re diving into the world of “cool mom” style with Cassidy Crockett, creator of the viral Cool Monologue series and the ultimate observer of what stylish women are actually wearing on the streets of New York. Cassidy breaks down the real-life outfit formulas that make women look effortlessly pulled together — from the denim brands worth investing in to the high-low shopping tricks that make luxury style more accessible. We talk capsule wardrobes, winter fashion trends, and how to rebuild your personal style after a life shift, whether that’s becoming a mom, changing careers, or stepping into a new chapter. If you’ve been craving a wardrobe reset, fresh outfit inspiration, or simply want to feel excited about getting dressed again, this episode is your ultimate cool-girl fashion playbook — no matter your age or life stage. Connect with Molly Sims:   / mollybsims     / mollybsims   Recent Purchases: https://shopmy.us/mollysims Blog: https://mollysims.substack.com/ Connect with Emese Gormley:   / emesegormley     / emesegormley   Recent Purchases: https://shopmy.us/emesegormley Blog: https://substack.com/@emeseg Connect with Cassidy Crockett   / coolmonologue     / coolmonologue     / cassidycrockett     / cassidycrockett_   Recent Purchase: https://shopmy.us/shop/casscrock Blog: https://coolmonologue.substack.com/ All Products Mentioned: https://shopmy.us/shop/collections/31...

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The Cool-Girl’s Guide to Fall: Marci Hirshleifer on Blazers, Denim, Bags & Timeless Investments

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Ultimate Spring Edit: What to Buy, What to Skip & What’s Trending in Fashion, Wellness, + Beauty!

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How to Follow Signs From the Universe — with Psychic Medium MaryAnn DiMarco

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Mom Read Strangers and We Need to Talk: Carol's Book Club | Honest To Pete

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Oprah & Jillian Turecki on Looking Within to Improve Your Relationships

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Cool Mom Closet Tours || Molly Sims

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Summer 2026 Fashion Trends: What's Actually Selling with Gab Waller

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Sofia Richie’s Stylist Wants You to Know: Underrated Brands, Summer Staples + Nailing Quiet Luxury

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Oprah with Belle Burden on the Collapse of Her 20 Year Marriage & Her Bestselling Memoir

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Eileen Fisher, Janessa Leone bag, Colleen Allen House coat and more…

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The Truth About Ozempic Face, Filler Mistakes, and Fixing Your Skin