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

Podcast Summary:

Lipstick on the Rim – “How to Dress Like a Cool Mom: The Jeans, Sweaters & Capsule Staples Every Woman Needs”
Hosts: Molly Sims & Emese Gormley
Guest: Cassidy Crockett (@coolmonologue)
Release Date: December 16, 2025

Episode Overview

This fun, fast-paced episode is a style survival guide for moms (and anyone who wants practical, pulled-together looks). Hosts Molly Sims and Emese Gormley are joined by Instagram’s “Cool Monologue” Cassidy Crockett. Throughout the conversation, they decode “cool mom dressing,” favorite denim and sweater brands, and how to embrace effortless chic through capsule wardrobes, all with the backdrop of real life: hectic mornings, post-baby body changes, and wanting to look good—even on three hours of sleep.

Key Discussion Points & Insights

1. The Birth of the ‘Cool Monologue’ & the Allure of Cool Mom Style

Cassidy shares how she started observing New York’s “cool moms,” developing a series that makes “being a mom aspirational, not frumpy.”
- “I just decided to call them cool moms... It’s women whose personal style isn’t defined by motherhood, but who figured out who they are.” – Cassidy Crockett [05:35]

2. What Is a ‘Cool Mom’ Outfit?

The consensus: it’s less about following trends, more about fit, material, and effortless confidence.
- “It’s clothing that fits really well and is really good material, and it just has to seem like you are wearing the outfit. Effortless.” – Cassidy [08:44]

3. Staple Pieces for All Seasons of Life

Practical must-haves: great jeans, a fun belt, loafers or flats, a quality sweater (layered with a pop of white shirt), and versatile coats.
Brands mentioned throughout:
- Jeans: Redone, AYR, Live Love Lenny, The Row, Moussy, Levi’s (low loose cut), Mother (mixed reviews), High Sport (“amazing cropped capri”).
- Sweaters: The Row (Ophelia), La Ligne, Cos, Jenni Kayne, Nadam (“cool toned camel cashmere”).
- Coats: Toteme, Jenny Kane, Quince (“so lush, you’d swear it’s $400, but it’s $150”), Moncler (cropped, unique textures), Miu Miu (“the puffy of the moment”).
- Shoes: Tony Bianco Gatsby Loafers (“so comfy, looks like YSL & The Row”), Celine Abbey flats, Wales Bonner x Adidas Sambas, Dr. Scholls clogs.

4. Winter Trends & Cool-Weather Essentials ([16:03]–[19:00])

Western-inspired looks (fringe, cowboy boots, thick collared sweaters)
Deep v-neck and bordered sweaters
Camel tones
Animal prints making a big comeback, especially leopard
Notable quote: “Leopard’s a neutral! You can wear it with everything.” – Cassidy [18:48]

5. Shoes & Accessories

Loafers, flats (chunky or with socks), and investment belts.
On navy and black: “I don’t like rules... I love navy and black together.” – Emisha [22:24]
Bags: Verified (“underrated real suede, $500–600”), vintage Chanel (“dream bag”), The Row Margaux bag (some find clunky), Kate bags (the woven style, impossible to get online).
Belts: B-Lo The Belt, Bottega, The Row, Celine lookalikes, belowthebelt.com.

6. Jewelry That Looks Luxe Without the Price ([30:13]–[31:36])

Layering custom charm jewelry from Heart; Dorsey for luxe, lab-grown diamond tennis necklaces.
Moms prefer to travel with lab-grown or faux jewelry for practicality—parallels with “fakes” for Birkin bags, as authenticity is less important than utility on-the-go.

7. The Capsule Wardrobe Deep-Dive ([32:52])

Capsule dressing is “the most realistic thing for busy women” — repetition isn’t boring if your base pieces are quality.
- “The whole point is you have pieces that are going to look great on you, fit well, and take away the stress of getting dressed.” – Cassidy [32:56]
Favorite capsules: high-waisted pant from High Sport, loafers/flats, white shirt, neutral color palette.
“Very Audrey Hepburn!”

8. Style Icons & Influences

Jenna Lyons (“obsessed, her material choices taught me everything”), Lauren Santo Domingo, and the effortless “Upper East Side” grandma for “aspirational vibes.”
- “Downtown, you can see when people are trying hard… On the Upper East Side, they don’t try, they’re just rich!” [38:52]

9. Investment Piece Philosophy

Jeans, a great cashmere sweater, and a belt—those are forever. “The jeans might change, tops might change, but you can always wear a belt you love.” – Cassidy [25:26]
Emese on blazers: “A great blazer… you’ll be able to see if it’s cheap or not, so invest in one quality piece.” – Emisha [27:36]

10. Event Dressing & The Power of Shoes

Don’t stress about head-to-toe sparkles; a black dress plus a “fun, rhinestone shoe” always works.
Crop-capri pants (“Audrey Hepburn trouser plus a flat equals instant chic”), animal print shoes, and statement glasses as “cool mom” identifiers.

Notable Quotes & Memorable Moments

“Making being a mom, making someone in their 40s or 50s, seem like a really aspirational thing… It always has been for me.” – Cassidy, [07:54]
“Leopard is a neutral.” – Rosie & Cassidy, [18:48]
“More moms actually travel with their lab grown or fake diamond rings and earrings than their real ones.” – Emisha, [31:17]
“I think a belt is an accessory that makes or breaks your outfit.” – Emisha, [26:37]
“Capsule dressing is the most realistic thing there is. You trust these pieces, they’re quality, they take the stress out.” – Cassidy, [32:56]
“If I could go back, I’d tell my 10-year-old self: It will happen. You just have to believe in it, even if you feel a little silly.” — Cassidy on manifestation, [39:42]
“The chicest people are out in the morning.” – Cassidy, [39:17]

Rapid Fire ‘Cool Girl Confessional’ // Timestamps + Highlights

[36:45] NYC Coffee Shop: “Interlude in Tribeca. The coolest moss… and Robert Pattinson/Suki Waterhouse are regulars.”
[37:11] Go-to Outfit in a Rush: “Loose black pants, cashmere sweater, white tee, loafers or jeans.”
[37:20] Favorite Designers: “Lulu desane, and for sweaters, Toteme, Nadam.”
[37:48] Icon Forever: “Jenna Lyons. And Lauren Santo Domingo.”
[38:06] Beauty Can’t Live Without: “Natasha Denona concealer. If you have to cover something really red and nothing works, use this.”
[38:25] Neighborhood for People Watching: “SoHo or Tribeca. But Upper East Side grandmas are next level.”
[39:15] Day or Night Person: “Wish I was a morning person—the chicest people are out in the morning.”

Final Thoughts & Manifestation

Cassidy shares her belief in manifestation and encourages listeners (and her 10-year-old self) to not abandon childhood dreams simply because they seem far away. “If you believe it, you actually take tiny steps towards it, and eventually, with a little luck, it’s yours.” [39:42–40:44]

What's Next for Cassidy

Cassidy plans to launch a new series: visiting “cool moms’ closets” and sharing their real-life style strategies. “Talk about their favorite way to style things and turn it into a quick reel… just go from there.” [41:17]

Summary Table of Wardrobe Staples & Brands

| Wardrobe Staple | Cassidy’s Picks & Recos | Affordable Options | |------------------------|---------------------------------------------------------|-------------------------------| | Jeans | Redone, AYR, Levi’s low loose, Moussy, Live Love Lenny, The Row | Mother, High Sport | | Sweaters | The Row Ophelia, La Ligne, Cos, Nadam, Jenni Kayne | Quince, Cos, Nadam, Toteme | | Belt | Below the Belt, The Row, Bottega, Celine look-alikes, Ralph Lauren | Below the Belt, Ralph Lauren| | Shoes | Tony Bianco Gatsby Loafer, Dr. Scholls clogs, Celine Abbey, Wales Bonner Samba | Tony Bianco, Dr. Scholls | | Coats | Moncler (cropped), Toteme, Miu Miu, Jenny Kane, Quince | Quince, Jenny Kane, Toteme | | Jewelry | Heart (custom charms), Dorsey | Dorsey, Heart | | Bags | Verified, vintage Chanel, The Row Margaux, Kate (woven style) | Verified, Kate |

Key Takeaways

Good fit, quality material, and confidence are the keys to “cool mom” style.
Capsule wardrobes make every day easier—and less likely you’ll panic about having “nothing to wear.”
Investment pieces (jeans, sweater, belt, blazer) are worth the splurge.
Mix high and low: You don’t have to spend designer money for cool factor (Quince, Heart, Dorsey, High Sport for under-the-radar finds).
Accessories transform an outfit: shoes, belts, bags, glasses—don’t skip them.
Trends to try: deep v-neck sweaters, bold belts, animal print, unique puffers, navy with black, and colored accessories.
Manifestation matters: “If you believe it, you’ll make your dream wardrobe and life happen.”

For more: follow @coolmonologue, @mollybsims, and @lipstickontherim. Find previous episodes, products, and blog content at mollysims.substack.com.

Podcast Summary:

Episode Overview

Key Discussion Points & Insights

1. The Birth of the ‘Cool Monologue’ & the Allure of Cool Mom Style

Cassidy shares how she started observing New York’s “cool moms,” developing a series that makes “being a mom aspirational, not frumpy.”
- “I just decided to call them cool moms... It’s women whose personal style isn’t defined by motherhood, but who figured out who they are.” – Cassidy Crockett [05:35]

2. What Is a ‘Cool Mom’ Outfit?

The consensus: it’s less about following trends, more about fit, material, and effortless confidence.
- “It’s clothing that fits really well and is really good material, and it just has to seem like you are wearing the outfit. Effortless.” – Cassidy [08:44]

3. Staple Pieces for All Seasons of Life

Practical must-haves: great jeans, a fun belt, loafers or flats, a quality sweater (layered with a pop of white shirt), and versatile coats.
Brands mentioned throughout:
- Jeans: Redone, AYR, Live Love Lenny, The Row, Moussy, Levi’s (low loose cut), Mother (mixed reviews), High Sport (“amazing cropped capri”).
- Sweaters: The Row (Ophelia), La Ligne, Cos, Jenni Kayne, Nadam (“cool toned camel cashmere”).
- Coats: Toteme, Jenny Kane, Quince (“so lush, you’d swear it’s $400, but it’s $150”), Moncler (cropped, unique textures), Miu Miu (“the puffy of the moment”).
- Shoes: Tony Bianco Gatsby Loafers (“so comfy, looks like YSL & The Row”), Celine Abbey flats, Wales Bonner x Adidas Sambas, Dr. Scholls clogs.

4. Winter Trends & Cool-Weather Essentials ([16:03]–[19:00])

Western-inspired looks (fringe, cowboy boots, thick collared sweaters)
Deep v-neck and bordered sweaters
Camel tones
Animal prints making a big comeback, especially leopard
Notable quote: “Leopard’s a neutral! You can wear it with everything.” – Cassidy [18:48]

5. Shoes & Accessories

Loafers, flats (chunky or with socks), and investment belts.
On navy and black: “I don’t like rules... I love navy and black together.” – Emisha [22:24]
Bags: Verified (“underrated real suede, $500–600”), vintage Chanel (“dream bag”), The Row Margaux bag (some find clunky), Kate bags (the woven style, impossible to get online).
Belts: B-Lo The Belt, Bottega, The Row, Celine lookalikes, belowthebelt.com.

6. Jewelry That Looks Luxe Without the Price ([30:13]–[31:36])

Layering custom charm jewelry from Heart; Dorsey for luxe, lab-grown diamond tennis necklaces.
Moms prefer to travel with lab-grown or faux jewelry for practicality—parallels with “fakes” for Birkin bags, as authenticity is less important than utility on-the-go.

7. The Capsule Wardrobe Deep-Dive ([32:52])

Capsule dressing is “the most realistic thing for busy women” — repetition isn’t boring if your base pieces are quality.
- “The whole point is you have pieces that are going to look great on you, fit well, and take away the stress of getting dressed.” – Cassidy [32:56]
Favorite capsules: high-waisted pant from High Sport, loafers/flats, white shirt, neutral color palette.
“Very Audrey Hepburn!”

8. Style Icons & Influences

Jenna Lyons (“obsessed, her material choices taught me everything”), Lauren Santo Domingo, and the effortless “Upper East Side” grandma for “aspirational vibes.”
- “Downtown, you can see when people are trying hard… On the Upper East Side, they don’t try, they’re just rich!” [38:52]

9. Investment Piece Philosophy

Jeans, a great cashmere sweater, and a belt—those are forever. “The jeans might change, tops might change, but you can always wear a belt you love.” – Cassidy [25:26]
Emese on blazers: “A great blazer… you’ll be able to see if it’s cheap or not, so invest in one quality piece.” – Emisha [27:36]

10. Event Dressing & The Power of Shoes

Don’t stress about head-to-toe sparkles; a black dress plus a “fun, rhinestone shoe” always works.
Crop-capri pants (“Audrey Hepburn trouser plus a flat equals instant chic”), animal print shoes, and statement glasses as “cool mom” identifiers.

Notable Quotes & Memorable Moments

“Making being a mom, making someone in their 40s or 50s, seem like a really aspirational thing… It always has been for me.” – Cassidy, [07:54]
“Leopard is a neutral.” – Rosie & Cassidy, [18:48]
“More moms actually travel with their lab grown or fake diamond rings and earrings than their real ones.” – Emisha, [31:17]
“I think a belt is an accessory that makes or breaks your outfit.” – Emisha, [26:37]
“Capsule dressing is the most realistic thing there is. You trust these pieces, they’re quality, they take the stress out.” – Cassidy, [32:56]
“If I could go back, I’d tell my 10-year-old self: It will happen. You just have to believe in it, even if you feel a little silly.” — Cassidy on manifestation, [39:42]
“The chicest people are out in the morning.” – Cassidy, [39:17]

Rapid Fire ‘Cool Girl Confessional’ // Timestamps + Highlights

[36:45] NYC Coffee Shop: “Interlude in Tribeca. The coolest moss… and Robert Pattinson/Suki Waterhouse are regulars.”
[37:11] Go-to Outfit in a Rush: “Loose black pants, cashmere sweater, white tee, loafers or jeans.”
[37:20] Favorite Designers: “Lulu desane, and for sweaters, Toteme, Nadam.”
[37:48] Icon Forever: “Jenna Lyons. And Lauren Santo Domingo.”
[38:06] Beauty Can’t Live Without: “Natasha Denona concealer. If you have to cover something really red and nothing works, use this.”
[38:25] Neighborhood for People Watching: “SoHo or Tribeca. But Upper East Side grandmas are next level.”
[39:15] Day or Night Person: “Wish I was a morning person—the chicest people are out in the morning.”

Final Thoughts & Manifestation

What's Next for Cassidy

Cassidy plans to launch a new series: visiting “cool moms’ closets” and sharing their real-life style strategies. “Talk about their favorite way to style things and turn it into a quick reel… just go from there.” [41:17]

Summary Table of Wardrobe Staples & Brands

Key Takeaways

Good fit, quality material, and confidence are the keys to “cool mom” style.
Capsule wardrobes make every day easier—and less likely you’ll panic about having “nothing to wear.”
Investment pieces (jeans, sweater, belt, blazer) are worth the splurge.
Mix high and low: You don’t have to spend designer money for cool factor (Quince, Heart, Dorsey, High Sport for under-the-radar finds).
Accessories transform an outfit: shoes, belts, bags, glasses—don’t skip them.
Trends to try: deep v-neck sweaters, bold belts, animal print, unique puffers, navy with black, and colored accessories.
Manifestation matters: “If you believe it, you’ll make your dream wardrobe and life happen.”

For more: follow @coolmonologue, @mollybsims, and @lipstickontherim. Find previous episodes, products, and blog content at mollysims.substack.com.

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Summary

Podcast Summary:

Episode Overview

Key Discussion Points & Insights

1. The Birth of the ‘Cool Monologue’ & the Allure of Cool Mom Style

2. What Is a ‘Cool Mom’ Outfit?

3. Staple Pieces for All Seasons of Life

4. Winter Trends & Cool-Weather Essentials ([16:03]–[19:00])

5. Shoes & Accessories

6. Jewelry That Looks Luxe Without the Price ([30:13]–[31:36])

7. The Capsule Wardrobe Deep-Dive ([32:52])

8. Style Icons & Influences

9. Investment Piece Philosophy

10. Event Dressing & The Power of Shoes

Notable Quotes & Memorable Moments

Rapid Fire ‘Cool Girl Confessional’ // Timestamps + Highlights

Final Thoughts & Manifestation

What's Next for Cassidy

Summary Table of Wardrobe Staples & Brands

Key Takeaways

Summary

Podcast Summary:

Episode Overview

Key Discussion Points & Insights

1. The Birth of the ‘Cool Monologue’ & the Allure of Cool Mom Style

2. What Is a ‘Cool Mom’ Outfit?

3. Staple Pieces for All Seasons of Life

4. Winter Trends & Cool-Weather Essentials ([16:03]–[19:00])

5. Shoes & Accessories

6. Jewelry That Looks Luxe Without the Price ([30:13]–[31:36])

7. The Capsule Wardrobe Deep-Dive ([32:52])

8. Style Icons & Influences

9. Investment Piece Philosophy

10. Event Dressing & The Power of Shoes

Notable Quotes & Memorable Moments

Rapid Fire ‘Cool Girl Confessional’ // Timestamps + Highlights

Final Thoughts & Manifestation

What's Next for Cassidy

Summary Table of Wardrobe Staples & Brands

Key Takeaways