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Lipstick on the Rim

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

Lipstick on the Rim

Sony Music

Society & Culture, Fashion & Beauty, Arts

4.3978 Ratings

🗓️ 16 December 2025

⏱️ 42 minutes

🧾️ Download transcript

Summary

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. A Sony Music Entertainment production.  Find more great podcasts from Sony Music Entertainment at sonymusic.com/podcasts and follow us at @sonypodcasts  To bring your brand to life in this podcast, email podcastadsales@sonymusic.com Mentioned in the Episode: https://shopmy.us/shop/collections/3114942 Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0

Train Dreams is now nominated for five Critics' Choice Awards, including Best Picture, Best Actor, and Best Adapted Screenplay,

0:08.0

and two Golden Globe Awards, including Best Actor Joel Edgerton.

0:12.0

I don't know where the years go.

0:13.0

It is also nominated for four Independent Spirit Awards.

0:16.0

Figured out, let me know. I'd like to ask for a few back.

0:19.0

And winner for Best Adapted Screenplay from National Board of Review. New York Magazine hails it as the best picture of the year. Train Dreams, only on Netflix. You know how some people swear by their 12-step routine? Yeah, I'm more of a five minutes and let's go kind of person. That's why I love Merit Beauty. Simple, clean essentials that actually make you look polished without the extra fuss. I'm more of a five minutes and let's go kind of person. That's why I love Merit Beauty,

0:37.7

simple, clean essentials that actually make you look polished without the extra fuss.

0:42.1

Merit is a minimalist beauty brand that makes elevated makeup and skincare design to help you look

0:46.7

put together in minutes. I've been using their parks for about a year and I am obsessed.

0:52.1

The flush bomb is probably my favorite. It gives that perfect natural glow

0:55.6

like you just came back from a walk outside. It's buildable, creamy, and never cakey. There's a reason

1:01.0

one is sold every 30 seconds. It's that good. Then there's a minimalist, which I keep in every

1:05.9

single one of my bags. It works double duty as a both a foundation and a concealer. So you can be your whole face in about two minutes, a little under the eyes, a quick swipe for any redness on your cheeks, blended in with your fingers, and you're done. It's what I reach for when I want to look fresh, but not overdone. And on the days I don't feel like wearing makeup at all, Merritt's great skin serum is my absolute go to. It gives that hydrated, plumpy, dewy look. Like you've had eight hours of sleep and a green juice, even if you haven't. What I love most is that everything from Merritt feels effortless and wearable. Clean formulas, beautiful packaging, and products that make getting ready simple again. Right now, Merit Beauty is offering our listeners, their Santer makeup bag with your first order at Meritbeautcom. That's M-E-R-I-T-Beautcom to get your free signature makeup bag with your first order. Meritbeauty. Hey, I'm Molly Sims. And I'm Emma Shagormley. We're two girls obsessed with one thing. Beauty. And by that, we mean everything that makes you look and feel beautiful.

2:04.1

We're calling on our favorite health experts, industry insiders, and friends to answer all

2:08.6

your beauty questions.

2:09.8

With a drink in hand.

2:11.1

Definitely with a drink in hand.

2:12.9

You're listening to Lipsick on the Rim with Molly Sims.

2:21.0

You know that feeling when you wake up,

2:23.7

look at your closet and think,

2:27.4

I have nothing to wear.

2:30.6

I think whether it's post-baby, post-career pivot, or just a new chapter in your life,

...

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