It still makes me laugh, and it still feels true, and it points at something bigger than a trend cycle. We spent a few years being told that luxury meant restraint — no logos, no color, just very good beige, worn very quietly. And there’s a version of that which is genuinely beautiful. But somewhere along the way it became a costume too, its own kind of uniform. Talking it through with Betsy sharpened it for me: real luxury isn’t the absence of noise. It’s the presence of you.

We used Carolyn Bessette Kennedy as the example, and it’s the right one. No logos, no obvious price tags, and somehow the most quietly commanding woman in any room she stood in. That wasn’t restraint. That was a woman who knew exactly who she was and dressed accordingly. You could put her in a J.Crew t-shirt and people would ask where to get it. That’s not a clothing trick. That’s a confidence trick, and the clothes are just the delivery mechanism.

This is the second time Betsy’s joined me on the podcast, and it’s not lost on me that the conversation goes deeper every time. Last time we talked about her path to New York. This time we got into the parts of styling nobody puts in a caption — the parts that happen in the fitting room, not on the sales floor.

She told me she loves when clients cry. Not because she’s unkind, but because she’s seen it enough times to know what the tears actually mean. Clothes have been telling a story about us the whole time, whether we meant them to or not, and most of us don’t stop to ask what that story is until we’re standing in a closet full of things we don’t recognize anymore. Betsy’s read: that moment isn’t a crisis. It’s information.

She talked about the women coming to her after a GLP-1 journey — bodies changed, closets suddenly full of things that don’t fit the way they used to, or fit fine and feel wrong anyway. Her instinct isn’t to send them shopping. It’s to wait. Let the body settle. Let the person underneath the change catch up to what happened before you hand her a new uniform to hide in. I think about the postpartum client she mentioned, nine months out, wanting more clothes immediately — and Betsy telling her, not yet, let’s give this some room. That’s not a styling philosophy. That’s just good care, dressed up as one.

The other thread running through this episode is one I feel every time I build a collection: the death of the one-and-done piece. Betsy’s clients keep showing up looking for a single dress for a single event, and she keeps redirecting them toward separates — toward things that can leave the party and go somewhere else the next morning. It’s the whole argument for a piece like the Lexington Jacket, or the Tuxedo Dress split into its parts. Not because “versatile” is a marketing word. Because cost-per-wear is a real number, and a piece that only shows up once a year is expensive no matter what it cost.

We got into suiting too — how a single suit, taken apart, is really six or seven outfits wearing a disguise. The jacket over a red skirt instead of the matching trouser. The blazer with jeans on a plane, the shoes packed separately because you always wear the jacket on the flight. I built our suiting to be worn this way on purpose — the androgynous cut wasn’t an accident, it was a rejection of the idea that a woman’s suit has to prove she’s still soft underneath it. Sometimes the point is the structure. Sometimes strong shoulders are the whole outfit.

If there’s a single thread through everything Betsy and I talked about, it’s this: try it on. The jeans you don’t think are you. The color you’ve been avoiding since your twenties. The blazer with the skirt instead of the trouser. Betsy’s line has stuck with me — nobody remembers what you had for breakfast, and nobody’s going to remember what you wore to the grocery store either. The only person keeping score is you. So put the sequin jacket on for a Tuesday and see what happens.

— Lindsay

The Well-Dressed Mind is available on Apple Podcasts and YouTube. If you missed our first conversation with Betsy Beaman, it’s worth going back to.

I flew into Dallas less than 48 hours before we sat down together. Couldn’t sleep. Went down the Jenny B. Davis rabbit hole at some hour I’d rather not admit to — her styling work, her writing, her career history — and by the time I put my phone down I had about ten thousand things I wanted to ask her.

That’s a good sign, in my experience. The best conversations start before they start.

Jenny is a licensed attorney, an award-winning journalist, a published author, an editorial fashion stylist, a professor at SMU, and — I want to make sure this gets the attention it deserves — a certified Star Wars cosplayer who has performed at Star Wars Celebration in Chicago and London. She has attended New York Fashion Week every year since 2007. She has been photographed by Bill Cunningham. She launched two fashion lines of her own, earned a Macy’s Emerging Designer placement, and got a New York Times write-up. She is currently in her third year of a doctoral program at SMU while working full-time.

She grew up in a hippie household with a potter mother and a history professor father who made beer and grew grapes. She was a German major at Arizona State. She went to law school because she didn’t want to spend her life worrying about money — and because, as she puts it, law school doesn’t teach you the laws. It teaches you how to find things, how to think, and how to work your ass off.

She never planned to be an entrepreneur. She calls herself the accidental one.

What struck me most in our conversation — and I’ve been thinking about it since — is how Jenny describes the through line of her career. It wasn’t a plan. It was a series of discoveries: finding out she could do something, figuring out she could professionalize it, and then doing it. Over and over, across fields that seem unrelated until you meet her and realize they’re completely coherent.

Law taught her to think. Journalism taught her to find the story. Styling taught her that clothes are never just clothes — they’re communication, intention, a signal to the room before you’ve said a word. Teaching taught her that learning is different when you’ve lived. She told me that if you don’t feed your brain, your brain eats itself. I wrote that down.

She also said something that I’ve been sitting with since we recorded: time passes whether you do the thing or not. She started her doctoral program in her fifties, mid-career, while working full-time, because the time was going to pass regardless. She didn’t want to look back and think — I wish I had done that.

I find that kind of thinking clarifying in a way that’s almost uncomfortable. It removes the excuse of timing. It removes the idea that there’s a right moment to begin something.

When I looked through Jenny’s styling work the night before we recorded — the work she’s done for 360 West, for clients, for editorial shoots — what struck me wasn’t just the beauty of it. It was that it made me want to buy things. There’s a difference between a beautiful photograph and a photograph that makes you feel something, want something, reach for something. Jenny’s work does the second thing. That’s not a technical skill. That’s a point of view.

We talked about Amy — our brand persona, the woman we design for, the filter we run everything through. When I showed Jenny the idea, she got it immediately. She called it a brand persona. I called it a wall of women we’re trying to serve. We meant the same thing.

This is the kind of conversation I started The Well-Dressed Mind to have. Not about fashion as decoration, but about fashion as a reflection of how people have built their lives, their identities, and their sense of self. Jenny B. Davis has built something genuinely rare — a career that doesn’t fit a category, informed by a life fully and curiously lived.

We’re eventually doing a part two. There are still about ten thousand things I want to ask her.

— Lindsay

Listen to this episode of The Well-Dressed Mind wherever you get your podcasts. And if you don’t feed your brain, your brain eats itself. Consider yourself warned.

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Shop Lindsay's Look:

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Follow Lindsay Nicholas New York on Instagram – @LindsayNicholasNewYork

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas

Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Shop Lindsay's Look:

Jackie Criss Cross Top in Black - https://lindsaynicholasnewyork.com/products/jackie-criss-cross-top-in-black-early-access-sale?_pos=4&_psq=jackie&_ss=e&_v=1.0

Bleecker Street Pant in Chartreuse - https://lindsaynicholasnewyork.com/products/bleecker-street-pant-in-chartreuse?_pos=1&_psq=bleecker&_ss=e&_v=1.0

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Follow Lindsay Nicholas New York on Instagram – @LindsayNicholasNewYork

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas

Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Shop Lindsay's Look:

Frill Crewneck Shell in Black - https://lindsaynicholasnewyork.com/products/frill-crewneck-shell-in-black

Gold Chunky Chain Belt - https://lindsaynicholasnewyork.com/products/elsewhere-co-gold-chunky-chain-belt-the-elsewhere-co_pos=1&_psq=chain+belt&_ss=e&_v=1.0

Follow Lindsay Nicholas New York on Instagram – @LindsayNicholasNewYork

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Shop Lindsay's Look:

Frill Crewneck Shell in Black - https://lindsaynicholasnewyork.com/products/frill-crewneck-shell-in-black

Gold Chunky Chain Belt - https://lindsaynicholasnewyork.com/products/elsewhere-co-gold-chunky-chain-belt-the-elsewhere-co?_pos=1&_psq=chain+belt&_ss=e&_v=1.0

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Follow Lindsay Nicholas New York on Instagram – @LindsayNicholasNewYork

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas

Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes.

New episodes drop monthly.

Shop Lindsay's Look:

Frill Crewneck Shell in Black - https://lindsaynicholasnewyork.com/products/frill-crewneck-shell-in-black Sakura Blossom Scarf - https://lindsaynicholasnewyork.com/products/sakura-blossom-silk-scarf?_pos=1&_psq=sakura+blossom&_ss=e&_v=1.0

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Follow Lindsay Nicholas New York on Instagram – @LindsayNicholasNewYork

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

On today’s episode of The Well-Dressed Mind, Becca joins host Lindsay Nicholas to talk about her path through the world of advertising, the lessons she’s learned at the helm of top agencies, and how her personal style has evolved along the way.

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Shop Lindsay's Look: Frill Crewneck Shell in Black - https://lindsaynicholasnewyork.com/pr...

Shop Becca's Look: Disco Glitter Top in Shiraz - https://lindsaynicholasnewyork.com/pr...

Lace Skirt in Floral with Nude Slip - https://lindsaynicholasnewyork.com/pr...

Hosted by Lindsay Nicholas Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York

ABOUT THE WELL-DRESSED MIND

What does it mean to dress—and live—with intention? Hosted by Lindsay Nicholas, CEO & Creative Director of her namesake brand, Lindsay Nicholas New York, The Well-Dressed Mind features candid conversations with smart, stylish women about ambition, reinvention, and the transformative power of clothes. New episodes drop monthly.

Follow Lindsay Nicholas New York on Instagram –  @LindsayNicholasNewYork 

Visit us online: www.lindsaynicholasnewyork.com

Hosted by Lindsay Nicholas

Produced by Sam Esquivel, Ally Beans, and Lindsay Nicholas New York