Kennedy Fashion

Summary

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United States of Kennedy – "Kennedy Fashion"

Podcast: United States of Kennedy (iHeartPodcasts)
Episode Date: December 8, 2025
Hosts: George Civeris, Julia Claire
Guest: Avery Trufelman (host of Articles of Interest, creator of "American Ivy" series)

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Episode Overview

This episode dives into the enduring legacy of Kennedy family fashion—how they’ve helped shape and symbolize American style for generations. Hosts George Civeris and Julia Claire invite fashion podcast host Avery Trufelman to unpack the nuances of "preppy" fashion, how it's intertwined with American identity, and how each generation of Kennedys—from Jack and Jackie to JFK Jr. and Carolyn Bessette—helped define (or subvert) this style. The episode explores not just the style, but its class, racial, and cultural implications, wrapping up with a look at the Kennedy descendants’ approach to fashion today.

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Key Discussion Points & Insights

1. The Kennedy "Look": Preppy as American Classic

• [04:01 – 06:52]
  • The classic Kennedy look conjures images of Ivy League preppiness: khakis, button-downs, “worn in” leisurewear on Cape Cod lawns.
  • Avery: “Preppy clothes have become classic clothes. Like, when we call something timeless or classic, we're talking about preppy clothes usually… even when we look at Carolyn Bessette Kennedy and people are like, oh my God, so classic. So pared down, so elegant. It's just kind of a 90s version of preppy clothes…” [06:52]
  • Preppiness persists because it projects both comfort and respectability—what Avery calls its "undying power," despite changing trends.

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2. Preppy Fashion: Origin, Evolution, and Social Meaning

• [07:34 – 14:55]
  • Preppy style is rooted in Ivy League collegiate looks, evolving from practical sportswear to the dominant signifier of upper-middle-class “timelessness.”
  • Avery: “This is clothing that really should have gone out of style a long time ago... but for some reason it still has this power, it still has this appeal, and it truly should have gone away, at least in the 60s, but it will not die.” [07:42]
  • The style’s elitism is both celebrated and subverted by those who wear it—especially when adapted by Black artists (Vampire Weekend, Kanye West, Pharrell) or reimagined by Millennials.
  • Preppy attire can serve as “respectability politics”—projecting trustworthiness and upper-class status even in the absence of wealth or "real" establishment credentials.
  • Avery on political optics: “All George Santos had to do was dress a little preppy, and people were like, oh, I should elect this man. You know, it's. It's crazy what people will do, how. How differently they'll treat someone in a collared shirt.” [14:11]

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3. Kennedy Fashion Moments: Myths and Cultural Shifts

• [19:05 – 23:52]
  • The “hatless JFK” myth: Contrary to legend, JFK actually wore a top hat at his inauguration—yet his generally hatless style was still radical for the era and may have signaled the growing dominance of sunglasses as a cool, modern accessory.
  • Avery’s theory: “My pet theory is this is everything to do with the rise of sunglasses. Because hats and sunglasses used to serve really similar purposes. And he's kind of the first president you see in shades a lot, which also, I think, helped contribute to his cool imagery.” [20:27]
  • The Kennedy leisurewear aesthetic helped cement "preppy" as aspirational: It’s tied to inherited privilege (“your khakis are supposed to be dirty and, like, ragged at the end... you're supposed to inherit these clothes from your dad”), projecting effortless wealth and nonchalance. [23:06–23:38]

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4. Race, Respectability, and the Meaning of Shabbiness

• [23:52 – 25:57]
  • The “lived-in” preppy look—frayed sweaters, old khakis—is class-coded and, Avery argues, racially specific.
  • “So the shabbiness is a whiteness taking the world for granted.” [24:19]
  • For Black Americans and other minorities, the expectation to look tidy and presentable ("Hygiene Olympics") is often a matter of respectability and social access, not mere style.

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5. Jackie Kennedy: The Aristocratic Outlier

• [25:57 – 36:24]
  • Jackie Kennedy’s style was more overtly “cosmopolitan,” drawing on French couture and projecting an almost royal aura, in contrast to her husband’s approachable collegiate look.
  • Avery: “She kind of provided this new version of America that was so worldly and cared about fashion, so cosmopolitan... It is a move that is a little aristocratic.” [26:26]
  • The rise of off-the-rack clothing (via Brooks Brothers) made men’s style accessible and “democratic,” whereas women—like Jackie—were left to define and maintain their own fashion standards.
  • Factoid: Every US president since Madison (except Reagan and Carter) wore Brooks Brothers; even Trump and Obama did.

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6. Media, Gender, and Fashion's Democratization

• [32:42 – 36:01]
  • Jackie Kennedy’s impact as a fashion icon was amplified by the rise of television and the change in media—her youth and glamorous, tailored look stood out on screen.
  • “She was as approachable as JFK's style was. Her style was almost a little bit less approachable because... she had this like model-esque body and she was famous for the shift dresses... made by houses like Chanel and Christian Dior...” [33:27]
  • The male core of preppy style left women to “improvise”—Jackie found her own feminine incarnation of American aristocracy.

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7. The Kennedy Women and Gendered Preppy Style

• [42:21 – 43:54]
  • Even women's preppy fashion was "borrowed from the boys"—and early iterations (like Brooks Brothers pink shirts for women) felt almost transgressive.

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8. JFK Jr., Carolyn Bessette, and the 90s Preppy Reboot

• [43:54 – 47:40]
  • JFK Jr. and Carolyn Bessette refreshed the Kennedy brand with a “quiet luxury” that mixed borrowed American preppy and new minimalist European (especially Japanese) elements.
  • “They are... extremely 90s. Because didn’t she work at Calvin Klein?... she had one part of her fashion inspiration... classic American sportswear, and the other part was like super cool Japanese Issey Miyake.” [44:18]
  • Black clothing, oversized silhouettes, and influences from grunge and streetwear quietly modernized—without abandoning—the family ethos.

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9. Preppy Style’s International Echoes (Especially in Japan)

• [51:20 – 54:05]
  • Preppy style, while iconically American, gained a cult following in Japan, as exemplified by the "Take Ivy" book—which was originally meant to show Japanese youth how to wear Ivy League style properly, challenging the perception that these were “beggar clothes.”
  • This cross-cultural exchange contributed to the rise of Japanese fashion as a global force.

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10. Quiet Luxury, Tax Law, and Modern Wealth Signaling

• [54:26 – 56:50]
  • The resurgence of minimal, luxe-but-understated “quiet luxury” among the wealthy is a response to social and economic factors, including the decline of the estate tax and social media’s “microtrend” churn.
  • Avery: “I think wealthy people don't want to call attention to themselves anymore because they don't contribute to society... they are, you know, like, don't look at me like Mark Zuckerberg, you know, these wealthy people are like, don't get mad at me... Anything that could look like excess might call attention to the way they actually live.” [54:34, 54:47]

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11. Where are the Kennedys Now? Contemporary Preppy & Its Complications

• [57:15 – 61:38]
  • The Kennedy descendants continue to “cosplay” preppiness for public consumption—even self-consciously (RFK Jr. in Vineyard Vines).
  • Avery: “He can put on this Kennedy costume and he can do it very well.” [58:35]
  • Preppy style retains its strong associations with WASP-iness/whiteness (“Vineyard Vines and Lily Pulitzer feels vaguely white supremacist to me” – Julia [59:59]), even as its history is also shaped by Jewish, Black, and Japanese creators and adopters.

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Notable Quotes & Memorable Moments

• On the persistence of preppy style:
  Avery Trufelman: “It truly should have gone away, at least in the 60s, but it will not die. It simply will not die. This old antiquated look that like really almost doesn't fit our lifestyles anymore.” [07:42]

• On respectability and the power of a collared shirt:
  Avery: “All George Santos had to do was dress a little preppy, and people were like, oh, I should elect this man.” [14:11]

• On the meaning of shabbiness and racial codes:
  Avery: “The shabbiness is a whiteness taking the world for granted.” [24:19]

• On Jackie’s cosmopolitanism vs. American preppiness:
  Avery: “She kind of provided this new version of America that was so worldly and cared about fashion, so cosmopolitan... It's very different than how Americans are quote, unquote, supposed to be. It's almost like this Edith Wharton throwback.” [26:26]

• On Brooks Brothers and democracy:
  Avery: “Alexandre de Tocqueville was like, this is amazing. You kind of can't tell who's rich and who's poor in this society. It's an extremely middle class society. Everybody is just walking around in these suits. You know, back in Europe, it was like the kings wore jewels and the paupers wore rags. And in America, we all just sort of wear suits.” [29:20]

• On the inescapable imagery of the Kennedys:
  George Taveras: “The Kennedy family is a strong enough brand that you always picture something like some kind of guy. And yet each generation, it has changed so much...” [61:52]

• On modern quiet luxury:
  Avery: “People don't want to show off their wealth, I really do think is like directly related to the negligence of Congress to regulate the tax code and how much everybody hates rich people now…” [55:16]

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Key Timestamps

| Time | Segment | |-----------|--------------------------------------| | 04:01 | Introduction to Kennedy fashion | | 06:52 | Evolution of preppy fashion | | 14:11 | Preppy as respectability politics | | 20:27 | Sunglasses replacing hats—JFK’s coolness | | 23:06 | Preppy lived-in look & inheritance | | 24:19 | Shabbiness, whiteness, and respectability | | 26:26 | Jackie O’s cosmopolitan fashion | | 29:20 | Brooks Brothers & democratic fashion | | 33:27 | Jackie as the first modern style icon| | 36:24 | Gender and preppy style for women | | 43:54 | JFK Jr., Carolyn Bessette, and 90s style | | 51:20 | Preppy’s journey to Japan ("Take Ivy") | | 54:34 | Quiet luxury, social class, and tax avoidance | | 57:15 | Contemporary Kennedys: RFK Jr. and Jack Schlossberg | | 61:52 | Preppy style as Kennedy brand metaphor|

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Final Thoughts

The episode wittily and insightfully traces how Kennedy fashion morphs across decades, merging pop culture, political optics, class dynamics, race, and gender to shape what Americans see as “timeless.” It demystifies preppy’s rise from privileged outlier to default American classic—while remaining (ironically) an ever-evolving costume. Through the Kennedys, style is shown as both symbol and mask—at once aspirational, approachable, and indelibly loaded with meaning.

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For listeners: The episode blends deep historical context, sharp commentary, and playful takes. Even if you’ve never obsessed over Kennedy style, you’ll come away seeing those khakis and button-downs—and what they mean—a little differently.

Transcript

[Avery Trufelman]

This is an iHeart podcast.

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[Avery Trufelman]

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[Avery Trufelman]

I just want to entertain people and.

[George Taveras]

Make a living From Focus Features they.

[Avery Trufelman]

Had a dream I want to sing.

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I want to dance. I want to garden.

[Avery Trufelman]

I want a cat.

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[George Taveras]

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[Avery Trufelman]

So good.

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[George Taveras]

I'm George Severis.

[Julia Claire]

And I'm Julia Claire and this is.

[George Taveras]

United States of Kennedy, a podcast about our cultural fascination with the Kennedy dynasty. Every week we go into one aspect of the Kennedys story and today we are talking about the Kennedys relationship with fashion.

[Julia Claire]

Jackie's pink Chanel suit and pillbox hat. Jack's defiantly hatless presidency. JFK Jr. S 90s baggy pants and backwards baseball caps. And of course RFK Jr. Weightlifting and rock climbing in only tight jeans.

[George Taveras]

Fashion legend but the type of fashion the Kennedys are most known for is the kind of worn in khaki driven New England look that you're under undoubtedly already picturing. Imagine all the Kennedy boys throwing around the pigskin at the compound. In a word, preppiness.

[Julia Claire]

So we thought who better to join us to discuss Kennedy fashion than Avery Trufelman, the host of the popular fashion podcast Articles of interest, whose 2022 series American Ivy broke down the history of preppy fashion.

[George Taveras]

Avery welcome to United States of Kennedy.

[Avery Trufelman]

Thanks for having me.

[George Taveras]

I want to start by doing something every writer loves or just quoting you back to yourself.

[Avery Trufelman]

I.

[George Taveras]

We found this Vanessa Friedman column from last year. It was about RFK Jr. Who mercifully we won't make you talk about.

[Avery Trufelman]

But oh please, I love talking about this Olivia Nutzy Ryan.

[George Taveras]

I guess that's true. We are, I will say we're recording the day that the Olivia Nuzzi book is coming out, so it is especially relevant.

[Avery Trufelman]

Let's go that to you, Bobby.

[Julia Claire]

And you know what? Happy pub day to her.

[George Taveras]

Shout out to Olivia.

[Avery Trufelman]

I have been really enjoying the drama. I'm sorry, Olivia.

[George Taveras]

No, I have, too. And I have to say no. She is. And in moral way. I know. I can't. I can't get into my complex feelings about her, but I'm. I'm. I'm. I'm both horrified and also like, you go, girl.

[Avery Trufelman]

But.

[George Taveras]

But not really. Don't quote me on that.

[Avery Trufelman]

No, no, it's terrible. It's all awful. But it is just like. I don't know. I think everybody in journalism is like, oh, my God, journalism's alive and well. Look at these journals. I know. Battling it out on this giant public forum.

[George Taveras]

Yeah. It really seems very. The 2025 version of people having sort of a back and forth via essay writing on the New York Review of Books or something.

[Julia Claire]

Yeah.

[Avery Trufelman]

It feels like no one does this anymore. Yeah.

[Julia Claire]

I think it would only be better if everyone involved adopted transatlantic accents. 100% to be talking about this.

[George Taveras]

True. Yes.

[Avery Trufelman]

Yeah. So anyway, he's not off limits as to me. I'm talking about Junior right now.

[George Taveras]

So Vanessa asked you about Bobby Kennedy Jr's sense of fashion, and you said he is cosplaying as a Kennedy. This is a quote. He's cosplaying Lou Kennedy said Avery Trufelman. And then this is not your quote. This is Vanessa's editorializing, which says doubling down on a manner of dress that is deeply associated with the Kennedy name, even though that association itself came from its own form of WASP cosplay, at this point, it has become a very powerful tool. So I think that's a great place to begin because I wanted to ask, when you hear Kennedy fashion, what do you think? What to you is the Kennedy look?

[Avery Trufelman]

Well, there's like a platonic ideal, you know, the Camelot Kennedy look. But then there have been so many other Kennedys. That look evolves and grows on its own. In a word, it's preppy. But really. And this is my whole hill that I'll die on is like, preppy clothes have become classic clothes. Like, when we call something timeless or classic, we're talking about preppy clothes usually, which is kind of interesting. And so I think even when we look at Carolyn Bessette Kennedy and people are like, oh, my God, so classic. So pared down, so elegant. It's just kind of like a 90s version of preppy clothes, even though it is evolving and it is changing and it is different. So I'd say those classic, timeless, but ultimately preppy.

[Julia Claire]

You have almost a bit of surprise in your voice that the preppy style has become associated with. With timelessness and classic style.

[Avery Trufelman]

Well, I mean, I personally am not surprised because I did a whole series about preppy clothes. So I spent like a lot of years of my life dedicating myself to studying this. But I do think once you sort of examine where preppy clothes come from and all the different evolutions they've gone through, it is kind of weird because this is clothing that really should have gone out of style a long time ago. It's very interesting that when you look at images of someone wearing whatever, a button down shirt and khakis in the 40s, that's usually not how fashion works. It doesn't just stay. And unlike other fashion trends, it's just sort of grown and grown and grown and more and more people started wearing it. And you'd think at some point that would make it uncool or like take the meaning from it. And it didn't. You know, for some reason it still has this power, it still has this appeal, and it truly should have gone away, at least in the 60s, but it will not die. It simply will not die. This old antiquated look that like really almost doesn't fit our lifestyles anymore.

[George Taveras]

And the 60s is when obviously JFK was president and when Jackie was in the White House. Like it is. There's something about preppiness. And you know, I'm saying this purely as a hobbyist and not as a fashion expert, that it's almost so uncool that when a cool person takes on the preppy look, it almost makes them cooler because they can pull it off 100%.

[Avery Trufelman]

Like, look at backpack wrap and like Kanye and Vampire Weekend. That whole era of the extremely cool people wearing these dorky clothes, Miles Davis wearing a seersucker suit, it somehow does not get cooler than that.

[George Taveras]

And I think not to say that JFK was, you know, the epitome of cool, but I do think the point that you slash Vanessa Friedman are making, that they are doing a form of WASP cosplay is sort of part of that. It's like part of the fascination is that, oh my God, they're Catholic and Irish.

[Avery Trufelman]

Exactly.

[George Taveras]

And yet they are dressed like wasps.

[Avery Trufelman]

Well, also, you have to consider the context again, like the 60s preppy clothing has been, or, you know, before it was preppy, it was called Ivy. And it was around for a long, long time, basically the 20th century. And it seemed as though by the 60s it was like, okay, enough. This was the explosion of youth culture, the explosion of fashion culture, the explosion of advertising. It was like, these clothes are not really viable anymore. Especially because Ivy style was considered this colleg look. And when you think about it like now we think of preppy clothes as semi formal, but at the time it came from doing sports and like being on college campuses. And so you'd wear like your tennis shirt to go to whatever, your dining club and go to class and you'd wear sneakers. It was like this extremely casual style that was like built on American college campuses. And this was so massive, especially after World War II, because you get this new creature called a teenager, which kind of didn't exist anymore. You were like a child and then you were an adult and you went to war or you got a job and suddenly there's this new generation. They're these people who don't have to go to war, they don't have to get a job, but they're young. But what do you do and how do you dress for this? And so sort of de facto this college look became. There were, there were pop up stores all over the United States called like Ivy shops and like Ivy style shops. And this is where you would dress like, you know, this is like the teenage look. And then so in the 60s, there's obviously a way new teenage look. The teenager is established. Youth is. They're not just trying to look young, they're trying to actually say something. But the funny thing is, especially in the 70s, you start to see this nostalgia for preppy clothes. This is like, you know, in the 70s, it's when all these movies that take place in the 50s come out like American Graffiti and like Grease and everyone being like, oh man, remember back when the world was simple, before it was so complicated. So yeah, not only were the Kennedys being like, oh my God, he's a Catholic, but he represents this simpler time, this idealism before the world got so complicated and everyone started wearing like fringe and all these crazy patterns and everyone was gender bending. And you know, it's funny because you kind of see Zoran Mamdani doing a version of it wearing just his kind of shitty suit supply suit. Ashley Fetters Malloy in the Washington Post had this great piece that was like, you know, he's dressing like every millennial guy who needed a suit 10 years ago.

[George Taveras]

Completely.

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[Avery Trufelman]

Which is comforting. No one's intimidated by. A friend of mine just saw Zoran in a museum off duty, and that guy is stylish. Like, he does not dress like that on his own. He's, like, wearing a little baseball cap and, like, a cool jacket. Like, he is very stylish. He knows.

[Julia Claire]

Well, you saw. You see his wedding photos. He's wearing this beautiful scarf. And that is a guy who knows how to dress.

[Avery Trufelman]

He knows how to dress. He knows style and his.

[George Taveras]

And if he doesn't, his wife certainly does. And even if. Even if he didn't, she would help him. It is such a conscious choice that somehow does work. And at every, like, he. At every point, he had the opportunity to, like, quote, unquote, upgrade, and he chose not to. And I think that was so smart.

[Avery Trufelman]

It's so smart, and it makes people comfortable, and it's just a little outdated. And so that's the thing. I also think the Kennedy look was a little outdated. It was kind of the version of the Zoron look at the time. It made people really comfortable.

[Julia Claire]

I also think that for both of them, they were both so young when they.

[Avery Trufelman]

Yes.

[Julia Claire]

When they came into political prominence, that it scared a lot of older people.

[Avery Trufelman]

Totally.

[Julia Claire]

What makes older people more comfortable than seeing a young man in a suit?

Yeah.

[Avery Trufelman]

A sort of fuddy duddy suit.

[Julia Claire]

What?

[Avery Trufelman]

A respectable young man. Yeah.

[Julia Claire]

Wow. This guy can't be radical. He's wearing a kind of shitty suit.

[Avery Trufelman]

A hundred percent. One hundred percent. And I think that's why this uniform, even though, again, this preppy logic, it defies everything because it's everywhere. You can buy a version of these clothes at Kohl's or something. They don't mean anything anymore. And yet they do. All George Santos had to do was dress a little preppy, and people were like, oh, I should elect this man. You know, it's. It's crazy what people will do, how. How differently they'll treat someone in a collared shirt.

[Julia Claire]

Totally. And I just want to say I didn't think of Zoran suits as shitty until this very conversation.

[Avery Trufelman]

They're nice.

[Julia Claire]

They're nice, but there's something about the cut.

[George Taveras]

And also sometimes his ties will just be, like, a little bit thinner than it was cool, you know, in 2024 or whatever.

[Julia Claire]

Maybe this is. This is like my millennial brain. I'm like, he looks great. I think he looks very sophisticated.

[George Taveras]

I mean, he looks like you go home for Thanksgiving or something. And the son that all the other Moms are like, God, I wish he was my son. Yeah, like he's doing really well for himself.

[Avery Trufelman]

He's not looking stylish. You never look at. You wouldn't see that guy on the street and be like, whew, wow.

[Julia Claire]

You know, maybe this is how divorced I am from style. Because I again, I think he is iconic. Oh yeah.

[Avery Trufelman]

I mean, he's also so cute.

[Julia Claire]

We'll be back with more United States of Kennedy after this break.

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[Avery Trufelman]

IBM.

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[Julia Claire]

And we're back with more United States of Kennedy.

[George Taveras]

I do want to say, you know, in terms of JFK's fashion at the time, one of the sort of funny things we came across when we were doing research for this episode is Avery, are you aware of Hatgate, which is that JFK was accused of not wearing a hat during his inauguration, which was. Oh yes, apparently everyone wore a silk top hat during their inauguration for a hundred years. And jfk, in fact Also wore one, but there was one photo where he had taken it off. And then that photo became so popular that people accused him of not wearing a top hat. So that was where the fashion conversation was at the time.

[Avery Trufelman]

Did they call it Hatgate at the time?

[George Taveras]

No, I just made that.

[Julia Claire]

That was before.

[George Taveras]

That would be amazing if they. If they predicted Watergate.

[Avery Trufelman]

Yeah, no, I had heard about that, but I didn't realize that he did actually wear the top hat. That's the greatest rebuttal.

[Julia Claire]

It's one of these things that's, like, very easily debunked. There are numerous pictures of him at his inauguration wearing said top hat. And it's funny because not only was he accused of not wearing a hat to his inauguration, he was then accused of basically ruining the hat industry. Like, he didn't wear a top hat to his inauguration, and therefore all men stopped wearing hats.

[Avery Trufelman]

Well, okay, I will say that in general, he was pretty hatless compared to his contemporaries. Beyond the inauguration, he was a pretty hatless guy.

[Julia Claire]

And there's a book called Hatless Jack.

[Avery Trufelman]

Oh, really? Okay. So my pet theory is this is everything to do with the rise of sunglasses. Because hats and sunglasses used to serve really similar purposes. And he's kind of the first president you see in shades a lot, which also, I think, helped contribute to his cool imagery. And I think it's also part of why the hat died. These sunglasses really became prominent and accepted. Cause you used to just cover your eyes with your brim from the sun. But also a big part of sunglasses were to, like, kind of, especially if you lived in a city, carve out space from other people, you know, to just like, pull your hat down and move through the crowds of people on Madison Avenue. And it just became a wider part of culture. Like, you see people just wearing sunglasses inside on the train just to, like, carve out a little space for themselves. And he was sort of living in that moment when sunglasses became ascendant. So I think that's part of it too.

[George Taveras]

I had never considered the rise of sunglasses as a real breaking point between old and contemporary. Like, if you see any sort of historical figure in sunglasses, that just makes them seem more modern. And it is true with Kennedy. He is the first president I think of as, like, obviously I was not alive then, but I think of him as like, okay, that's the era that the general era in which I was alive is the post war 60s and onwards era, 100%.

[Avery Trufelman]

And it totally adds to that. Youthful Hollywood, glamorous. And it's more outdoorsy you know, it's more active to wear sunglasses than to wear a hat when you're, like, rolling up your sleeves and playing football with the whole Kennedy family and all those, like, famous images, you know, or sailing. That's the other thing is the preppy clothing movement is also. I think the Kennedys biggest contributions were in their, like, off hour clothes. You know, when you see them, like sailing and playing football and wearing these preppy clothes that are really collegiate looking, like they look really young and they look really all American and they're just poster children.

[Julia Claire]

Yeah, it's kind of the advent of leisure wear. And I think that's where, you know, we have. Obviously there have been so many conversations in the last few years about the quiet luxury look, which is in many ways just this look that we're describing.

[Avery Trufelman]

Totally, 100%.

[Julia Claire]

But it's kind of like, do you have the money to do leisure activities?

[Avery Trufelman]

Yes.

[Julia Claire]

And also a lot of these clothes are very lived in. And there was a big conversation a few years ago when Knives out came out that the very well constructed sweater that Chris Evans is wearing in it has a lot of moth holes and it's very worn. And some people initially thought that that was unrealistic that someone who had that much money would have a sweater with a lot of holes in it, when in fact. It's exactly right.

[Avery Trufelman]

It's exactly right. Yeah. And I mean, if you read, you know, the seminal book on this, Lisa Birnbach's the Preppy Handbook, it says your khakis are supposed to be dirty and, like, ragged at the ed. Supposed to be a little worn in. And it's such a commentary on whiteness. Right. You're, like, supposed to inherit these clothes from your dad.

[Julia Claire]

Exactly.

[Avery Trufelman]

So well made. And it's also this not caringness, you know, this, like, you have nothing to prove, the world is yours.

[Julia Claire]

Nonchalance. Yeah, exactly.

[George Taveras]

Like your sweater is very, you know, it's the sweater that's in the closet of the Hamptons home. Like of. Of the Nantucket home.

[Avery Trufelman]

This thing up?

[George Taveras]

Yes, exactly. Like, it's like, oh, right, didn't this belong to Uncle Robert? And then you just put it on.

[Avery Trufelman]

And is the huge difference, I think, between the way that this style was repurposed in hip hop and especially in black fashion, especially when you see, like, Pharrell, it's all about looking clean and looking, like, fresh and looking new. And that is where racial dynamics come in. And it's. It's really fascinating. So the shabbiness is a whiteness taking the world for granted.

[Julia Claire]

That's so interesting that you say that, because there's been a big discourse online about the Hygiene Olympics or something like that. Some TikTok creators and people on Instagram talking about their hygiene routines. And then it's very often white creators being like, this is so performative. This is so crazy. When, in fact, this is the kind of the standard to which black Americans have been held for generations is that. That they had to be seen as neater and cleaner. And, you know, what is now considered, like, performative hygiene was so deeply intertwined with respectability and their ability to integrate into a white supremacist world. Yeah.

[George Taveras]

It's the fashion version of respectability politics. And especially when you look at it in terms of presidents, literally, JFK had truly, like, 15 STIs at every point. He was in the. This is like something we run into literally doing historical research for this podcast. I'm not making this up. And then now Trump is on his third marriage and has, like, a blended family, and it doesn't affect their respectability. Whereas, of course, if Obama had. Yes, exactly. If Obama so much as, you know.

[Julia Claire]

I don't know, sneezed on camera.

[George Taveras]

Yeah. Or wore, you know, God forbid, a beige suit. Not to be the. Say, you know, the beige suit. The most cliche example ever. But, yeah, the tan suit. Thank you. I want to talk. I want to sort of bring it into Jackie a little bit, because I think. Think you're absolutely right that the Kennedy fashion ethos is very sort of, like, effortless. And we're throwing around the pig skit, then we're throwing around a Frisbee, and it's very just.

[Julia Claire]

We're on the compound.

[George Taveras]

We're on the compound. It's very lived in. Whereas Jackie, the effort was clearly visible. Like, she was. She clearly was very passionate about fashion. She liked French designers, and she was wearing these super unique, bright color looks. And I think that was almost in contrast with the Kennedy vibe. As someone who studies fashion for a living, like, where does Jackie fit into American fashion historically?

[Avery Trufelman]

Yeah, I mean, that's the funny thing is she kind of provided this new version of America that was so worldly and cared about fashion, so cosmopolitan, you know, and to be so literate in all these designers and to enjoy them, and it is a move that is a little aristocratic. It's very different than how Americans are quote, unquote, supposed to be. It's almost like this Edith Wharton throwback. You know, I, like, go to France to get my couture clothes. And then come back. And I. And I do think she's, like, balanced out by the, like, all American preppiness of her husband. But it gives her this permission to be the cosmopolitan European. You know, she was a writer, she spoke French. She was kind of this queenly figure that she was able to be. You know, the interesting thing is I just want to talk about, like, Brooks Brothers really quickly, because Brooks Brothers is super duper important to talking about, like, how American presidents dress and how Americans dress and the origins of this preppy look. Today, Brooks Brothers is the oldest clothing company in the United States, which is incredible. Like, they weren't the first, but they are the one that has lasted until today, which is. Is extraordinary. Their history is out of control. Like, they were among the first generation of clothing companies that invented ready to wear clothes. Like, that's an American invention that you could buy clothes off the rack. Like, you used to buy cloth, and you'd bring it to your tailor and be like, make me a suit. Or probably you'd like, bring it to your wife and be like, make me a suit. But Brooks Brothers and many other companies. But Brooks Brothers was really, like, among this cohort, they were like, what if we just made the shirts already in a bunch of different sizes? And it totally changed the shopping experience because now people could try things on, you know, and it turned shopping into this activity that was this third space. You know, you could walk into these stores. It wasn't like a chore, like, going to buy, you know, buying fabric used to be like, oh, I gotta go buy milk. Now it became this, like, pleasurable thing. You could, like, try on these skins. And they were already there and they were already made, but they only existed for men. There were no ready to wear clothes for women. And it was considered a thing. Like, men, you are too busy to have to think about your clothes. We've already thought about it for you. Just come into our store and you can buy your clothes already. Women were shit out of luck. They had to keep up with the trends themselves. You know, they had to usually make their own clothes or get their own clothes made. And it fed into this idea that, like, oh, women are so obsessed with fashion because they kind of had to be. They didn't have an option. They didn't have somewhere to just opt out and have someone think about it for them. But for Brooks Brothers, it was this really. It was considered this all American invention because these suits were relatively affordable. At one point, Brooks Brothers had two locations. One was like, downtown by the docks for like the workers. And one was sort of uptown and fancy and everybody was kind of wearing these ready to made suits. And it was this shocking thing. Alexandre de Tocqueville was like, this is amazing. You kind of can't tell who's rich and who's poor in this society. It's an extremely middle class society. Everybody is just walking around in these suits. You know, back in Europe, it was like the kings wore jewels and the paupers wore rags. And in America, we all just sort of wear suits. Suits. And this was the whole point of democracy. Right? Like, we want to blend in. We want to be the medium. We want to, like, rely on each other. And so it was seen as this point of pride that like the President wore Brooks Brothers. You know, the President also blended in. He wasn't a king.

He was just one of the people. And okay, Brooks Brothers wasn't around to clothe the first four presidents, but they've clothed all the other presidents since, with the exception of two. Do you want to guess who they were? This is just a fun fact. Oh, the two presidents who didn't wear.

[George Taveras]

Brooks Brothers, are they older or more contemporary? I mean, I assume Trump did not wear Brooks Brothers.

[Avery Trufelman]

He does. There's a picture of Trump and Obama wearing Brooks Brothers suits standing next to each other.

[George Taveras]

Wow.

[Avery Trufelman]

Different ties. Yeah.

[George Taveras]

I mean, Reagan.

[Avery Trufelman]

Yeah, Reagan was one because he was like a Hollywood star. And his suit's custom made. It was too.

[George Taveras]

Correct me if I'm wrong, I'm going. But so we read this Women's Wear Daily Daily article that was talking about how Brooks Brothers at the time designed a suit with a slimmer outline, and that's the one that was then sort of popularized by jfk. Yeah, But I feel like then to your point, about fashion, especially men's fashion, becoming democratized, from what I understand, there was sort of a response to that. Where then with the advent of European and even Japanese fashion coming to America, then men did start caring about fashion a little later, like in the 80s and 90s. And then it became lame to wear Brooks Brothers. So it makes sense to me that Reagan during his era would want something more interesting.

[Avery Trufelman]

Reagan wanted something more interesting. And the other one who didn't want to wear it because he thought it was too fancy was Carter.

[George Taveras]

I was like, oh, that makes sense.

[Avery Trufelman]

Wear these old things that I found somewhere. But it was all just to say there is this precedent of the president even.

[Julia Claire]

That's the thing.

[Avery Trufelman]

Even Donald Trump, for all his pomp and circumstance, wears this kind of like plain looking suit. And so it's really up to like the wife to show the style. And so Jackie was the one who was allowed to be, you know, Melania is the one who's allowed to be like dripping in diamonds.

[Julia Claire]

And thank God for that.

[Avery Trufelman]

And thank God for that.

[George Taveras]

And she looks fabulous.

[Julia Claire]

I love.

[George Taveras]

And we're also actually we're recording this during the weeks long promo cycle of Michelle Obama's new book specifically about her fashion looks.

[Avery Trufelman]

Exactly.

[George Taveras]

But I wonder if have an insight into like to me, Jackie is the one that ushered in the era of like the fashionable first lady or even the press paying attention. And I might be completely wrong, but from what I remember like watching movies and reading things growing up, I know of Jackie as a fashion icon and then since then we have commented on how first ladies dress. Do you have any, any concept of what first lady fashion and first lady fashion expectations were like pre Jackie and post Jackie?

[Avery Trufelman]

I mean, not really. But the other thing is the media was so different.

[George Taveras]

True.

[Avery Trufelman]

You know what I mean? It's like there were images of her everywhere and she was so beautiful and she was so young. And while I'm sure there were like whatever daguerreotypes of different first ladies before I, it's just like a different order of magnitude. You know, the fact that she was like on TV like talking and moving and at 31, you know, that's the other thing is you don't have to dress that well to look good at 31 compared to other first ladies. You know what I mean? She just like naturally looked great in everything. So I think that was the other thing is like the media was really different and people had a different attitude. They wanted to relate to her.

[Julia Claire]

Right. And it was, you know, JFK's inauguration was the first to be televised and that was another big change. And it wasn't just that you were seeing photos of the first lady, you were seeing how she moved in the clothes as well. And she has such a natural elegance. She has this very willowy figure and clothes look incredible on her. And she was also wearing, to your point about the kind of royal aspect to her, she was as approachable as JFK's style was. Her style was almost a little bit less approachable because one, she had this like model esque body and she was famous for the shift dresses and all of these kind of figure hugging clothes that were made by houses like Chanel and Christian Dior and then later Halston and things like that. And yeah, there was something really aspirational and unapproachable about her style that every American woman at the time really aspired to. But, yeah, to your point, she was also young and wasn't wearing these very, like, matronly clothes of first lady's past. And then the ones that succeeded her.

[Avery Trufelman]

Yeah, I feel like they were just a perfect one, two punch. He was the college boy and she was the refined, you know, international queen. And they both helped get taken seriously by different demographics. It was this interesting sort of like, divide conquer thing. But of course, it's like, I don't. I wonder what my grandma thought of that. I wish I could ask someone who was, like, really considering voting for them what they thought. I was just watching Mad Men for the first time, and I don't know if you remember this or if you've seen it, but they were like, oh, no one's gonna vote for her. They're gonna hate her. They're gonna be jealous of her. And so I'm sure a lot of people thought that her look was, like, uppity. I'm sure it played everybody.

[George Taveras]

Yeah, I think for people that were viewing it in a more optimistic lens, it was sort of aspirational. And then for people who were already primed to hate her, it was like, why is she in a costume? You know, when there's inequality.

[Avery Trufelman]

Yeah, exactly.

[Julia Claire]

And to go back to the sunglasses of it all, she became so famous for her oversized movie star sunglasses. And again, it really does contrast the rest of the Kennedy style, which is very lived in. Her clothing was always so pristine, so fitted. Not a wrinkle to be seen. Cause I had always thought of the two styles as very complimentary, and I guess they are. But it's interesting that hers really was very individualistic.

[Avery Trufelman]

Yeah, Preppy's style is very much a male style. Even though there are, like, female versions of it. It's really menswear, by and large. And so she was kind of improvising her own version of it. Like, if preppy clothes are sort of the American version of aristocracy, she kind of had no choice but to go like aristocracy. Aristocracy kind of go, like, European completely.

[Julia Claire]

We're going to take a short break. Stay with us.

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[Steffi from Famous Footwear]

Hey, I'm Steffi. You may know me from your social feed. I go big for the holidays so I'm going to Famous Footwork because the best gifts are giving. Famous My friends and family are gonna love all these styles from Nike, Adidas, Crocs, New Balance, Skechers and more. With over 800 stores, you're never far from the perfect gift. So make your list and make it famous. Come in today for buy one pair. Get one half off at your local famous footwear or famous.com some exclusions apply.

[George Taveras]

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[Avery Trufelman]

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[George Taveras]

Hola.

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[Julia Claire]

And we're back with more United States of Kennedy.

[George Taveras]

Do you have any Jackie looks? Not to now become, you know, a. A gay fashion podcast, but do you have any, like, Jackie looks that are sort of. Of iconic to you? Like, for me, we talked about the Parker Posey movie the House of Yes, the other week, and the COVID of that movie at Blockbuster is, I think, where I first saw, like, the pink Chanel suit and the pillbox hat. But did you grow up thinking, I don't know, as someone who had a budding interest in fashion, did you think Jackie was cool or did you think she was lame?

[Avery Trufelman]

It's just so not like, you know, that's like a costume. Like, you see it and you're like, that's chic. But it's not like, I'm gonna go buy a pillbox hat and wear it. Which is also the funny thing. Right. We talked about how, like, Jack was so known for being hatless, and she's so known for her hats. They're so, like, her style is not really one for the ages. I mean, her vibe is maybe one for the ages, but it's fun to look at pictures of it, but it doesn't really feel applicable. There's never anything that I'm like, ooh, I'm gonna use that.

[George Taveras]

Yeah. It is funny that it could so easily make a sort of. Of nostalgic comeback, or, like, you could imagine a world in which just one little thing went a little left field, and suddenly Zara was making knockoff pillbox hats, but it just has never happened. Like, of all the things that could come back in a nostalgic way, that really is stuck in the 60s.

[Avery Trufelman]

Yeah. We just live a life that isn't conducive to hats anymore. I mean, look, we're all wearing headphones. Can you imagine?

[George Taveras]

We're all podcasting.

[Avery Trufelman]

Everybody's podcasting. How's anyone supposed to wear a hat? But, I mean, it's just a different.

[Julia Claire]

Yeah, it's just a different world for. For listeners at home. Obviously, you can't see me, but I am wearing a pillbox hat right now.

[George Taveras]

And it looks fabulous.

[Avery Trufelman]

Original hallways, your outfit.

[Julia Claire]

Thank you.

[George Taveras]

Because we mentioned JFK's lack of a hat, I do want to say there's another misremembered part of the inauguration that has to do with Jackie, which is that people remember her in this baby blue skirt suit. And in fact, it was more of a tan color and There was one Life Magaz photograph that was sort of color corrected in a specific way that made it look light blue, but in the same issue, like in the same package. You see other photographs and she's wearing sort of like a beige.

[Avery Trufelman]

Well, that's so interesting because Melania had that suit. Everyone's like, she's being Jackie O and it's all a lie.

[George Taveras]

Yeah, no, it is. It really is the one photo that was popularized of her. And color photography was also like still new at the time. And so people took it and ran with it. But yes, it was in fact sort of a neutral, like gray, beige color.

[Avery Trufelman]

Wow.

[George Taveras]

Wow.

[Avery Trufelman]

Funny.

[Julia Claire]

Yeah. That suit is currently housed at the JFK Presidential Library. And a lot of people are shocked when they see it in person because it's kind of iconically remembered as a robin's egg blue. And it's not.

[Avery Trufelman]

Wow.

[Julia Claire]

Yeah. I think the thing you said about preppy style being predominantly menswear is really interesting. Yeah.

[Avery Trufelman]

I think even when it's supposed to be worn by women, like even in the preppy handbook, they talk about it being like a very androgynous total style. And when I talked to women who were sort of encountering the preppy look for the first time at women's colleges, it was kind of amazing because it was this way that they were able to dress practically. You know, these were schools where you had to like check into your dormitory before 8pm and you'd wear pantyhose on Sunday. Like, horrible. A horrible world. But with the invention of the Ivy look, they were like, oh my God, we could wear sneakers. And one woman I talked to was like, let me send you a picture of me and my friend. And it's wild. Cause they just look like they're in boys. I mean, now they just look like they're in what we would call clothes. But at the time it really must have looked like drag. It must have looked really shocking. They were just wearing, you know, Brooks Brothers made a version of their classic button down oxford in pink. Because women used to go in and they'd go to the kids section and buy stuff. And when they made a version with like a Peter Pan collar that came in pink for women, everybody lost it. It was like on the COVID of Life magazine and the COVID of Vogue magazine. It was like finally, you know, something for women. But it was always supposed to be like borrowed from the boys was the look of preppy. And even though there are versions, it's like, you know, there's like a Lily Pulitzer version. And There are versions that are a little bit more like Southern cotillion coded. I think Jackie really had to like find her own way to be feminine within this framework.

[George Taveras]

Speaking of women that look amazing in button down shirts, I thought we could sort of transition into the next generation and talk a little bit about JFK Jr. And Carolyn Bessette. And I want to get into the intersection of preppiness on the one hand and, sorry to use this TikTok term, but quiet luxury on the other. How would you situate JFK Jr. And Carolyn Bessette within the general like fashion environment and fashion ecosystem of the 90s?

[Avery Trufelman]

Well, they are very 90s. They're like extremely 90s. Because didn't she work at Calvin Klein?

[George Taveras]

Yeah, she was sort of discuss. She like worked at Calvin Klein. Then he put her in charge of their VIP program. And so then she would be doing like fittings for VIP clients. And that's how she met Jon Jon, who I know we're not. You know, no one actually called him Jon Jon according to the Real Housewives. But yeah, she worked at Calvin Klein. But I feel like she had one part of her fashion inspiration was like classic American sportswear, and then the other part was like super cool Japanese Issey Miyaki.

[Avery Trufelman]

Yeah, yeah.

[George Taveras]

And I feel like it's almost the combination of those two that like produces the kind of quiet luxury, like the row vibe that we now think of as cool.

[Avery Trufelman]

Well, I do think it's like the introduction of black is really important. You know, the idea of wearing stuff that is black is not very preppy on the surface. Black is for funerals and black is for funerals. And then that was the whole thing. You know, in the 80s when Yoji Yamamoto burst on the scene making clothes that were like almost entirely in black. Some were white, but mostly black. And Rei Kawakubo emerged as what was the horrible racist thing they were calling it? Like here is Chicago. Chicago like it was supposed to be. And I believe at the time the people who wore comme des garcons in Japan were known as the crows because they were all just like wearing black. So I do think the introduction of international Japanese style really made black a very chic thing, because it was very shocking at first when they emerged with these like really kind of violent, dark, morose Runway shows, you know, as opposed to the French or the Italians who were having these like twirly big skirts. And then the Japanese had like holes in their, in their garments. So I think that's the biggest thing is that a lot of the styles really ultimately look the same. And the other thing is that Carolyn is leaning into this borrowed from the boys look. Her clothes do look oversized. They look like menswear. She's not trying to look. If she does wear a dress, it's like a very simple dress. It's not very femme at all, which is very preppy. But I do think the introduction of black is the big thing that she does.

[Julia Claire]

And to your point that you said earlier about what we now conceive of as preppy style should have gone out of style many times throughout the last hundred years and has been. I think what you see with JFK Jr. And Carolyn Bessette in the 90s, especially JFK Jr. Is kind of almost an injection of a little bit of grunge into preppy style, which is so interesting because grunge was like the antithesis of preppy style. The only similarity is the androgyny of it. I think it was like men and women were wearing who were, you know, had that grunge aesthetic, were wearing the same sorts of clothes. But you see JFK Jr. A lot of his silhouettes were less fitted than his father's. And I don't know, there were just certain. I look at pictures of him and there were. It was like grunge and streetwear mixed with preppy style. And I thought that was so interesting.

[Avery Trufelman]

Well, yeah, I think you're really hitting on this thing that we were getting at earlier with our, like, Zoran JFK discussion is like, these are people who are not. Not necessarily trying to get votes in their immediate future. And they are following trends. You know, they are dressing trendily. They are following a little bit of grunge, a little bit of hip hop, like, a little. They are moving with the styles of their time, even while keeping sort of whatever the family Kennedy look. They're not trying to look outdated in the way that might have been more politically savvy.

[George Taveras]

We'll be back with more United States of Kennedy after this break.

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[Avery Trufelman]

Me Sierra muna resena de quesoy un camino de fisil roccoso y empinado ques perada.

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[George Taveras]

And we're back with United States of Kennedy.

[Julia Claire]

One of the things that I keep coming back to that is so interesting about preppy style is that in every generation in which it has been popular, it is kind of a nostalgic choice. And it harkens back to the greatest generation, whatever you think that is. In the 60s, as you were saying, it should have died out because of the counterculture and youth culture. And then in the 70s and 80s, it became a nostalgic reach for the 60s. And then in the 80s again, it happened because obviously, like, the explosion of preppy culture really happened in the 80s, and it's just kept evolving. And it's interesting that you. You mentioned Japanese style being a big injection into fashion in the 90s, because since then, preppy fashion, which is this iconically American look, is very popular in Japan as well. And this book, Take Ivy, which is like a coffee table book that has all these iconic pictures from Ivy League schools picturing this classic American preppy style. And its authors are both Japanese.

[Avery Trufelman]

Do you know the story behind that book?

[Julia Claire]

No.

[Avery Trufelman]

So, okay, I did this series called American Ivy, and it threads the story of that book in with the history of preppy clothes. But long, long, long story short, that was just a book that was meant to accompany a film that was being shot at American college campuses to show people in Japan how Americans were wearing these clothes. Because in Japan, they thought that they were beggar clothes. They thought Ivy meant beggar. And because they had, like, holes in them, they thought they were super disrespectful. Like, kids were getting arrested for wearing preppy clothes in Japan. And so the founder of this store that had started replicating preppy clothes in Japan was like, I have to set this straight. And he set out to make a movie that he then wanted to show to various preppers, police precincts, to be like, this is how it's worn in America. You guys don't understand. It's, like, super duper different. But by the time he went to American college campuses to make this movie, and the book is just sort of like a side product, by the time they got there, it was like 1968, and it was, like, a little late. Basically, it was like a movie to show people in Japan who were afraid of getting arrested how Americans wear preppy clothes. But the whole story of how this look got appropriated in Japan, and, I mean, the preppy clothing is kind of responsible for. I don't want to say solely responsible, but it gave a huge jumpstart to Japanese fashion. And I don't know if we would have, like, Ryoji Yamamoto without it. I mean, there's so much more to the story.

[George Taveras]

But yeah, so I think for Carolyn Bessette, she, along with like Gwyneth and Kate Moss and various other sort of like skinny blonde women in the 90s, popularized a certain kind of effortless look. Oversized button down shirts, tailored pants, whatever. Why do you think that is kind of like making a comeback now?

[Avery Trufelman]

Honestly, I think a lot of it. I mean, this is kind of a longer answer than I think you were hoping for, but I do think a lot of it has to do with tax law.

[Julia Claire]

Sure.

[Avery Trufelman]

I think it's because the estate tax is all but dead. And I think wealthy people don't want to call attention to themselves anymore because they don't. They don't contribute to society.

They really, they really don't. Most of them don't make a taxable income and so they don't pay income tax. And so I think it's like very different than the wealth of the Gilded Age when people wanted to like wear little tiaras and show it off. They are, you know, like, don't look at me like Mark Zuckerberg, you know, these wealthy people are like, don't get mad at me. Don't look at me. Anything that could look like X us might call attention to the way they actually live.

[Julia Claire]

Yeah. Mark Zuckerberg, to your point, looks like he looks terrible. And he is. I would not even call what he's doing quiet luxury. I would call what he's doing like MMA podcast guy, cosplay.

[Avery Trufelman]

But I mean, the way that people are doing it now, you know, he has like these watches that cost.

[George Taveras]

Yeah.

[Avery Trufelman]

Ungodly, you know, these, like little things. You know, it's not about wearing like a nice suit. This is the quiet luxury bit of it. And I think that while this was already afoot in the 90s, it's only gotten worse and worse. And so I do think, you know, ever since the era of the preppy handbook, this idea of not showing off your wealth has been a thing. But I think this phenomenon, this like TikTok phenomenon of quiet luxury and this way that people don't want to show off their wealth, I really do think is like directly related to the negligence of Congress to regulate the tax code and how much everybody hates rich people now when they shouldn't. Like rich people should be contributing to society and it should be great.

[Julia Claire]

This is something that George and I were talking about off mic as well. It also seems like a direct response to the micro trend economy and how TikTok and other Social media platforms have created the. These trends that come at warp speed.

[George Taveras]

That it's just easier to be like, I'll stick to the classics and, you know, then remember, like, what length my shorts are supposed to be and how wide my pants are supposed to be and whether or not I should be wearing sambas versus, you know, gazelles or whatever.

[Avery Trufelman]

Yeah, yeah. Well, I also think in an era where we sort of live in this omnivorous world where you could zoom with anyone at any time or meet anyone at any time, it is also a way to, like, dress for the the most people. You know, it's this very, like, approachable, friendly look that's always a little professional and a little cool. It just kind of works for the ways that our lives are lived.

[George Taveras]

I want to end on the Kennedys that are currently in the news because it's always sort of funny to think about where this family is now. The two most high profile Kennedys right now are Jack Schlossberg and RFK Jr. Who's obviously, you know, in the Trump administration. Jack Schlossberg is sort of, I would say, fashion wise, wants to kind of have it both ways. Wants to both reference his background as a Kennedy while also being kind of like, cool and, you know, have, like, floppy hair and be shirtless, dancing on Tick tock, whatever. And then RFK Jr. There's a sort of combination of like, preppiness, but mixed with, like, roided out gym bro or something. What do you think about. You know, you can take your pick. Like, what do you think about either of them in terms of their fashion and in terms of where they fit into their family's legacy?

[Avery Trufelman]

Yeah, I just think RFK is really leaning into the cosplay of it. I think he's going like, old school preppy, you know, I mean, I'm not looking at pictures of him right now, but I just imagine him wearing like, little vineyard vines ties, you know, like, he's not.

[Julia Claire]

Well, Vineyard vines in and of itself feels like preppy cosplay because it is taken up such a notch.

[Avery Trufelman]

Exactly. Yeah. I just feel like he is kind of, again, it's this idea of being a little purposefully untrendy, and I think he's leaning into that. It's not a cool look and it's. So, as you said, he's like half roided out. Jim, bro, you can tell that's not really how he dresses in his life, but he can put on this Kennedy costume and he can do it very well.

[George Taveras]

Yeah, yeah. He can work out with jeans in the morning and then put on a crisp collared shirt in the evening. It's funny how Cheryl Hines has also occasionally, like, whipped out the more Jackie O silhouettes when it's time to, you know, make a public appearance. Because to me, she's so. I mean, not only is she a Hollywood actress, she's like a comedy person. I mean, she was like a Second City improviser. Like, she's not, you know, a sophisticated first lady. No offense. You know, I love her on carb, but it's just, you know, fact or fact. And it is funny to see her with this simple silhouette with a thin belt, and it's like baby blue or something. And they're going to some event that's like, you know, banning vaccines in Puerto Rico or something.

[Avery Trufelman]

Oh, God. Yeah. That's the thing that's really scary. I mean, there's a reason that, you know, in the Unite the Right march in Charlottesville, everybody wanted to wear collared shirts. It's as well, being like, we're your neighbors, we're approachable. It's a very powerful costume. And again, it shouldn't be. We all have access to this stuff. It shouldn't mean anything. And yet it does.

[Julia Claire]

And then again, going back to what we were talking about earlier, that's so inextricably linked to whiteness and a very particular. I think that, like, Vineyard minds. Lily Pulitzer feels vaguely white supremacist to me.

[Avery Trufelman]

Although, you know, it's really complicated also, because obviously the high priest of it is Ralph Lauren, and one of the earlier practitioners of preppy clothes was Jay Press, who was also a Jewish tailor. Like, there's a huge Jewish history to it. This Japanese history, this black history to it. Like, it really is not so. That's the other thing. It, like, takes on so many dimensions, and it's such a rich history, and yet it can still be diluted. People still can read it as this thing. It still means nice white neighbors.

[George Taveras]

And I think, like, young kids, not to sound old. Young kids that now are trying to dress preppy in, like, a cool streetwear way way, are more so emulating, you know, Tyler the creator, than they are.

[Avery Trufelman]

Exactly.

[George Taveras]

I don't know, people doing dressage or something.

[Avery Trufelman]

100%.

[Julia Claire]

100% human dressage, I like.

[George Taveras]

That's right.

This was very fun, and I feel like I'm ready to start a Pinterest.

[Julia Claire]

Well, I feel like I could talk about this forever. I think the first show, many different generations, it has meant a return to American glory, which is really funny. And I don't know, I just. I think it's really interesting how it's this iconic style that won't die.

[Avery Trufelman]

Yeah.

[Julia Claire]

And is really resistant to change, but also not as, you know, as we were talking about, with the way that, like, black celebrities have taken up the mantle of this style. It's endlessly modern as well.

[George Taveras]

I think that is something that is, you know, not to paint with too broad a brush, but that's in some ways how it's similar to the Kennedy family writ large. It's like the Kennedy family is a strong enough brand that you always picture something like some kind of guy. And yet each generation, it has changed so much and sort of like, evolved, like JFK and then JFK Jr. And now Jack Schlossberg. Like, they all clearly have the same DNA visually, but each one of them has, like, the twist, the 90s twist, the 20s twist, and it's sort of like an aesthetic that evolves along with American culture.

[Avery Trufelman]

Exactly. Exactly. Exactly.

[George Taveras]

Well, Avery, thank you so much. This was really fun, and thank you for taking the time to explain preppiness to us.

[Avery Trufelman]

It's fascinating. Thank you so much.

[Julia Claire]

So that's it for this week's episode.

[George Taveras]

Subscribe and follow United States of Kennedy for all things Kennedy.

[Julia Claire]

Every week, United States of Kennedy is hosted by me, Julia, Claire, and George Taveras.

[George Taveras]

Original music by Joshua Topolsky.

[Julia Claire]

Editing by Graham Gibson.

[George Taveras]

Mixing and mastering by Doug Boehm.

[Julia Claire]

Research by Dave Ruse and Austin Thompson.

[George Taveras]

Our producer is Carmen Laurent.

[Julia Claire]

Our executive producer is Jenna Cagle.

[George Taveras]

Created by Lyra Smith.

[Julia Claire]

United States of Kennedy is a production of I Heart Podcasts.

[George Taveras]

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[Avery Trufelman]

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[Avery Trufelman]

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[Avery Trufelman]

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[Julia Claire]

Get ready for your next TV obsession. All's feature Starring Kim Kardashian, Naomi Watts, Niecy Nash, Betts, Teyana Taylor. With Sarah Paulson and Glenn Close. A team of fierce female divorce attorneys leave a male dominated firm to start their own. Filled with scandalous secrets and shifting allegiances both in the courtroom and within their own ranks, these ladies know that Lawyers are a girl's best friend. Don't miss the two part season finale of All's Fair on December 9th on Hulu and Hulu on Disney. For bundle subscribers. Terms apply.

[Avery Trufelman]

This is an iHeart podcast. Guaranteed humor.