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Lilly Pulitzer and the Birth of Rich Girl Casual

26 Jan 2026

Transcription

Chapter 1: What was Lilly Pulitzer's early life like in Palm Beach?

1.415 - 23.136 Unknown

Why have three Gilmore Girls in a small town resonated with generations of fans? And what does a TV series that ended nearly two decades ago reveal about who we want to be? Generation Gilmore Girls is a brand new three-part podcast series that looks for answers where it all began, in Connecticut. Hosted by me, Chloe Nguyen, and produced by Connecticut Public.

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86.06 - 107.572 Claire Donald

So Rami's imagine this it's 1960 and you're standing in the middle of Palm beach, Florida, a place where the richest people in America are pretending to be very normal. Everyone is tan. Everyone is married to someone important and every woman is dressed exactly the same. Until one woman shows up, looking like a walking cocktail.

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108.994 - 128.858 Claire Donald

She's wearing colors that do not exist in nature, a dress that does not require a girdle, and she looks wildly inappropriate for a country club. Which is exactly why everyone could not stop staring. This is Lily Pulitzer. I have the fucking chills. She is our girl. I just like had a moment...

129.361 - 148.095 Claire Donald

but a dream you could say where I was just like, let's like, I feel like she's really preppy and you know, like sorority girls are obsessed with her. She was kind of big in the fifties and sixties. And then during research, I was like, there's so much connection to Jackie Kennedy and royalty. And I was like, she's so ram coded and let's cover her. Let's do it.

148.075 - 173.565 Tess Bellomo

I'm so excited because I think I will be surprised by the end of this episode because I have my preconceived notions about who she is because of what her legacy has kind of become. Well, what are your preconceived notions? Well, with Love and Light, like, I do imagine, like, very basic sorority girlies that are, like, prim and proper and probably with, like, not vibe with Ram.

173.585 - 175.247 Tess Bellomo

And that's putting women in a box, right?

175.43 - 191.575 Claire Donald

Look, I got some Lilly Pulitzer folders and pencils, I think, when I was a, because I was like, it's not my style for the clothing. But I was like, I will get some of the accessories. And she did, I mean, there were so many sorority accessories, like for every chapter, for every, it was crazy.

Chapter 2: How did Lilly Pulitzer's designs challenge 1950s fashion norms?

317.895 - 336.066 Claire Donald

Okay, so Lily Jr., Lily Jr., you could say. We love when this happens. I know, it is so cute. So her great-grandfather was this guy named Jabez A. Boswick, who was a Standard Oil partner. And we are talking...

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336.046 - 359.742 Claire Donald

like he was one of the original american oil tycoons he was a founding partner of standard oil do you have chills i literally have the chills i literally have the chills test oh my god i'm in wow full body chills no there is just something about this time where like you know if you're wealthy it's a very chic time if you're well you know if you're wealthy and white you're probably just sailing on through the 50s and 60s without a care in the world

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359.857 - 363.283 Tess Bellomo

Wealthy white and a man, like what problems do you have?

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363.424 - 364.405 Claire Donald

Very privileged.

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364.425 - 377.209 Tess Bellomo

And they're doing just fine. And it's obviously just like, it's just fun to hear stories about this because we just talk about so much struggle in history. So sometimes it's nice to like just take a break because we don't live in that world to be like, wow.

377.53 - 382.359 Claire Donald

A hundred percent. Yeah. We have to sometimes do episodes where you're just like, everything went perfectly right.

382.98 - 383.08

Yeah.

383.06 - 404.528 Claire Donald

It's just nice. And this woman was just drinking and living her best life, which all of us can wish for that and hopefully get that. I agree. So you know John D. Rockefeller? Yes. So he was the face of Standard Oil, and her great-grandfather was the brains and bankrolls behind it.

404.508 - 407.851 Tess Bellomo

He was a bankrolls behind it. Oh, my God. Oh, my God.

Chapter 3: What influence did Jackie Kennedy have on Lilly Pulitzer's brand?

479.854 - 492.692 Claire Donald

She has the fucking chills. Sylvia Plath, Rachel Lambert Mellon, who was a billionaire philanthropist, the daughters of Rockefeller, Vanderbilt, Morgan, and Boswick families all went to this school.

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493.113 - 496.698 Tess Bellomo

I didn't realize Sylvia Plath was rich.

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496.858 - 502.446 Claire Donald

I've tried to get into Sylvia Plath before, and then sometimes I'm like, I get overwhelmed, but we should cover.

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503.087 - 514.488 Tess Bellomo

We definitely should cover. Is the H silent? In what? Sylvia Platt. Is it Platt? Oh, is it? Or Platt? I don't know. We will do an episode on her. I read the bell jar once.

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515.43 - 517.214 Claire Donald

We will discover soon how to pronounce her last name.

517.435 - 518.417 Tess Bellomo

Yeah, I'm so sorry, you guys.

518.532 - 541.182 Claire Donald

it was plath but you know i don't know it very well could be one of us is right and that's great exactly that's why there's two of us yeah exactly um so this school was like on another level of course it was like one of the most famous and powerful girls schools in american history i saw this quote that was like it was the ivy league for girls before women were allowed into ivy leagues

541.82 - 547.614 Claire Donald

And it wasn't just a prep school. It was essentially a finishing school for future queens of money, politics, and culture.

548.155 - 558.888 Tess Bellomo

So was it training these women to be like the wives? It wasn't like... educating, making sure they have a huge education to run a company. It was like to run a household basically.

Chapter 4: How did Lilly Pulitzer's personal struggles shape her fashion career?

909.991 - 921.829 Claire Donald

Like, it's nice. Like, we're by the beach. Like, we're drinking, like, Miami Vices, whatever the fuck we're doing. And they were like, let's get pregnant and have a kid and just, like, start being a little, like, all-American dream.

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922.129 - 923.191 Tess Bellomo

So they're living there full time?

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923.511 - 924.432 Claire Donald

They're living there full time.

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924.452 - 925.594 Tess Bellomo

Okay. Got it. Got it.

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926.198 - 945.122 Claire Donald

And a quote from her business partner, this guy, his last name is Stolman. We'll figure out his first name soon. I did not write down his first name, but he worked with her for a long time in the brand. He said this about her, quote, she was a very, very good mother. Because she was born into wealth, she had the luxury of being eccentric.

945.482 - 951.97 Claire Donald

She didn't have the typical worries that a lot of people have of paying a mortgage, but she was also very sensitive to inequality.

953.215 - 962.65 Tess Bellomo

Well, the sensitive to inequality is huge. I mean, it's just so true. I know people say that money can't buy you happiness, but it really can help.

962.67 - 974.73 Claire Donald

Absolutely. What were we talking about? Oh, George Clooney the other day and Amal being like, what do they fight about? And it's like, of course they fight, but they're probably fighting a lot less than most couples that have been together that long.

975.13 - 980.978 Tess Bellomo

Financial stress is... I mean, yeah, it just puts so much stress on you.

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