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)

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.

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.

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]

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]

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.

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.

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.

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.

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.

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.

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]

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.

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]

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|

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.

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.