JFK vs. GHWB: Vote For America’s Preppiest President


The day has finally arrived! Yes Ivy Style readers, it’s your chance to vote on who was America’s preppiest president.

Here are the candidates and their qualifications:


John F. Kennedy

Spee Club
Family compound: Hyannis Port, Cape Cod
Hobby: sailing
Clothier: Chipp
Style signatures: sunglasses, no socks, Nantucket Reds


George HW Bush

Skull & Bones
Family compound: Kennebunkport, Maine
Hobby: tennis
Clothier: Norman Hilton
Style signatures: striped watch bands, boat shoes, madras

Now cast your vote! America’s past depends on it!— CC

[yop_poll id=”1″]

Patriotic bow tie by R. Hanauer.

54 Comments on "JFK vs. GHWB: Vote For America’s Preppiest President"

  1. Well apparently they both liked Shaggy Dog sweaters.

  2. Chewco L.P. (master) | November 7, 2016 at 5:55 pm |

    You just put up a post about how GHWB was indeed the preppiest prez and now look at the results.

    This vote is clearly rigged!

  3. Boy this is going to be a tough decision for me.

  4. I wanted to vote JFK but Bush is just naturally prep. There was an article on here, I believe, that explained that Jackie honed her husband’s style. Long live 41!

  5. If anyone is so magnanimously disinterested as to cast his vote against his party affiliation, I say to him “You, sir, are a gentleman and scholar”!

  6. This is tough, because as a Catholic I feel like I ought to vote for JFK, but on the other hand GWB has far stronger old money credentials.

  7. Like both of their styles. However, as a true Conservative, I personally don’t like the Bush family, but he was all around much more Ivy then JFK.

  8. GHWB for sure.

  9. @Dennis I had the same qualm but for this vote, the true WASP needs your vote.

  10. I voted Bush for two specific things that, beyond the listed “cred” they shared, Kennedy just didn’t have:

    – first, for all his athletic and military exploits, Bush had that somewhat ‘bumbling’ demeanor that’s born only of old money and true privilege (recall his bewilderment at how a supermarket checkout scanner worked); and

    – second, the large brood of offspring that includes not only public-minded high achievers, but also the embarrassing ne’er-do-well.

  11. Good rationale, Paul, and you got me thinking about Whit Stillman’s movie “Metropolitan” and the exchange about WASPs (or UHBs) being doomed to irrelevance.

    JFK represented optimism and the New Frontier, whereas GHWB, a generation later, represented the old WASP establishment, but at the time of its twilight.

    Kennedy, personally, was the tragedy of a noontime sun forced into blackout. Bush was a setting sun.

    So if one holds a fatalistic view of society, from the point of view of 2016, one could say Bush was “preppier” for representing not a beginning but an end.

    Then again, “preppiness” is characterized not only by tradition, but bright optimism. Which is why being a melancholy poet isn’t very preppy, but wearing pink and green is.

  12. I have a predilection for GHWB. His bumbling is for much the same reason as mine. When the 1st word that comes to mind is asseverate, gadarene, irenic, vituperative etc. you often find yourself seeking a less imperious or seigneurial word in order to not be judged or impunged. JFK’s acute satyriasis is dinstinctly antithetical to WASP/Preppy nature. I agree with Paul; the athletic and Naval background make this poll result fait accompli GHWB (Yale, S&B, CIA). Finally, I cannot hear GHWB’s mother pushing him to the same striving, rodomontade that Joe was constantly filling his kid’s heads with.

  13. Well, Bill, let’s not forget JFK served in the Navy also, exhibiting lots of derring-do in the PT109. But you’re also right correct that, over JFK’s shoulder, was always the spectre of Joe Sr.’s ambition. Very un-prep.

  14. I feel you Dennis, but GHWB definitely takes the preppy cake.

  15. I think that America’s love of the Kennedy family stems from the fact that they appeared to have fun. They were private but more public than the Bushes who, as WASPs, are naturally private. Also, the Kennedy brothers had movie-star looks and JFK’s literally being shot down in his prime truly secured his place in history. Along with this, he was fairly “preppy” in that he adopted and embodied an American lifestyle but was not to the manner born. If one really analyzes JFK, it is visible that he was not overly preppy. His wardrobe is due in part to where he vacationed (the laid-back sailing life of Cape Cod that he adopted) and to a lesser extent his schooling. Again, Jackie is also credited as having helped him become more sartorially sound. It is an interesting case study of how an immigrant family truly became a prominent, American family. The difference between the Bushes and Kennedys is, in one way, that one family got here before the other.

  16. Just can’t help but think that the Andover-Yale-Skull & Bones trajectory is the one that all the little pre-preps want to be launched upon. I personally always ask “What Would John O’Hara Most Lust After?”

  17. H H Huntington | November 8, 2016 at 1:35 am |

    If we’re talking about style, JFK should unquestionably be the hands-down winner. Crazy socks don’t mean charisma.

  18. Bıston Bean | November 8, 2016 at 2:57 am |

    GHWB: Preppy
    JFK: Trad

  19. Mitchell S. | November 8, 2016 at 6:47 am |

    If style counts, then Truman was unquestionably America’s best-dressed President. He was the only commander-in-chief to have been a haberdasher. The National Park Service has a great slideshow of some of the many custom suits Truman wore during his tenure.

  20. Here here, Mitchell S.

    Harry Truman was unquestionably America’s best dressed President. Preppy? No. Best Dressed? Absolutely. As Margaret used to say: “Dad always looked as if he just stepped out of a band box.”

    As to the poll at hand, GHWB by a landslide.

  21. Well, they both lived in a oversized, gaudy white mansion, so neither one! 😉

    I voted GWHB, but it was close.

  22. “They were private but more public than the Bushes who, as WASPs, are naturally private.”

    The Kennedys were arguably the most scripted and polished (for public consumption) family of the 20th century. To Joe’s credit, he, with his connections to Hollywood, knew how to do it well. They were a nauseatingly public family. One wonders how much image consultants and brand-obsessed marketers/advertisers have studied the not-so-subtlte promulgation of the Kennedys. If we stick with the old mythology of WASPy reserve and penchant for privacy, a good case can be made they were the least WASPy family in public life– ever.

    As for “Preppy”– not so sure. The padded, shaped-through-the-middle 2-button suits, straight collars, and overly styled hair. No thanks. If anything, JFK’s style served as a counterpoint to the prevailing style on Ivy League and prep school campuses at the time.

    He began wearing Chipp toward the end of his life, right? Hasn’t it been well documented that Chipp, engaged in custom work, wasn’t captive to any sartorial orthodoxy?

  23. S.E., spot on, they are by no means a WASPy family but they are American.

  24. White Pinpoint | November 8, 2016 at 11:01 am |

    Both were gentlemen enough not to have claimed that the election was “rigged” if they had lost.

    By the way, I like your snazzy new “selfie” CC.

  25. Depends on how you define “gentlemen”.

  26. A Bridge Too Far | November 8, 2016 at 11:41 am |

    Given that JFK was an Irish Catholic, the debate about how WASPy he was or wasn’t seems rather inane, at best. It’s because of Mr. Bush’s bumbling nature and also because Mr. Kennedy set new sartorial standards by going hat-less that I have a greater affinity towards JFK than GHWB, but that leaning is more modest than resolute. Both were great dressers and both good presidents.

  27. I went with JFK because IMO he exhibited far more “style” in his attire. He still looks pretty to me for a man birth date was 100 years ago next May.

  28. White Pinpoint | November 8, 2016 at 12:52 pm |


    I define “gentleman” as being the opposite of a vulgar, boorish, lout.

  29. Kennedy was the original, but Bush did it best.

  30. So, Mr. White Pinpoint, if that is your real name, does being a notorious philanderer fit into your definition of a gentleman as well?

  31. GHWB is a true gentleman, JFK was more of a politician in that he knew how to cover up his lies and negative personal details.

  32. @ABTF the poll isn’t on who is WASPy-er as there is only one WASP candidate, the article’s title clear states that it’s poll on who was the preppiest president.

  33. Vern Trotter | November 8, 2016 at 4:58 pm |

    No question here that it is GHWB. However, even though the term “preppy” was not coined yet, in future consider:

    Theodore Roosevelt
    Home Schooled
    Harvard (Porcellian)
    Columbia Law (dropped out)
    Col US Army
    Rough Riders: TR personally bought uniforms at Brooks Brothers for officers and men; most officers were from Harvard, Yale and Princeton; Tiffany bought state of the art Gatling guns for unit.
    Winner Congressional Medal of Honor
    New York City Police Commissioner
    Assistant Secretary US Navy
    Gov State of New York
    Vice President USA
    Youngest President of USA
    Winner Nobel Peace Prize

    Franklin D. Roosevelt
    Harvard (Fly Club; blackballed at Porcellian, biggest disappointment of life.)
    Columbia Law
    Assistant Secretary US Navy
    Gov State of New York
    President of USA–Elected Four Times; President during WW2

  34. A Bridge Too Far | November 8, 2016 at 5:02 pm |

    @GS – You think the definition of a politician is knowing how to cover up lies and negative personal details? LOL. Both GHWB and GWB were consummate politicians. I never got the sense that either was a deliberate liar nor worked hard at covering up personal negatives.

  35. A Bridge Too Far | November 8, 2016 at 5:07 pm |

    @Vern Trotter – Theodore Roosevelt was a great president (as was FDR). He was probably a little too athletic to be a preppy, though? Nevertheless, one of the all-time greats. What did he win the Nobel Prize for?

  36. @A Bridge Too Far – Nobel Peace Prize 1906

  37. A Bridge Too Far
    I think the Bushes are pikers compared to JFK. The man was in constant rut mode. The Bushes never had the human centipede that is the MSM covering for them. The Kennedys have always been reckless.

  38. @ABTF, being a liar is almost a requirement to be a politician. See Hillary Clinton, case and point.

  39. A Bridge Too Far | November 8, 2016 at 6:59 pm |

    @GS – Of course, Mr. Trump has the largest schnazz in the history of politics and he says he isn’t even a politician! Being a liar is a requirement of being a politician — you’ve gotten inebriated on the old kool-aid, there bud. Oh, yes, Lincoln, Eisenhower, Truman, Reagan, Coolidge, Jefferson and, of course, Washington — all first cousins of Pinocchio. Bloody liars, every last one of them!

  40. @ABTF I said it’s almost a requirement, meaning that not all politicians are but most are that is common knowledge. Also, Lincoln, Jefferson and Washington were not politicians in the modern sense at all. Eisenhower was an army man who loved his country, and Coolidge is only seen as a good president because he didn’t do very much. As for Truman, he was one of the good politicians as he wasn’t in it for the money, like Hillary and unlike Trump, as he owned a menswear shop. Hillary is an opportunist, she needs the job to live Trump doesn’t.

  41. @ABTF, funny how we’ve strayed from my original comment calling you out for misunderstanding the poll. I see Hillary has taught you how to pivot well.

  42. Ain’t democracy great?

  43. P Rainscott | November 9, 2016 at 2:27 am |


    It sure is. For the next four years, it looks like we’ll be able to choose black shirts or white sheets 🙁

  44. Looking back, a lot of 60s era Democrats had great Ivy style. If Christian or another Ivy Style writer/poster can find them, I’m sure there’s a goldmine of pictures of, for instance, Governor Endicott “Chub” Peabody and “Sarge” Reynolds of Virginia.

  45. Looks like navy suits with longer jackets will be in style for the next four years at least…

  46. Bradford Macmillan | November 9, 2016 at 11:14 am |

    @P Rainscott:

    And mourning bands for the rest of us.

  47. To say that Truman was not without political sin and just a haberdasher is to ignore his history in Kansas City prior to his appearance in DC. He was the Pendergast machine hand picked man to run the Jackson county, the county KC resides in. He was also a member of the KKK for political reasons. He often gets credit for his steering county contracts away from the machine, but that was only after Pendergast was busted. Truman was part of a political machine with connections to the mob and why since his time in Kansas City the state of Missouri runs the police dept. to this day instead of local control. Kansas City was the most wide open city at one time.

    That said he was a good president, but be careful of believing these heliographs of these politicians.

  48. Vern Trotter | November 9, 2016 at 4:54 pm |

    Of course, there is always Teddy Roosevelt’s son:

    Theodore Roosevelt lll
    Asst Secr US Navy
    Gov Puerto Rico
    Gov General The Phillipines
    Brigadier General US Army
    Winner Medal Of Honor for heroism on DDay and the Normandy Invasion

    As far as I know, the only father/son Medal Of Honor recipients.

  49. Vern Trotter | November 9, 2016 at 5:23 pm |

    Sorry, I forgot the subject was US Presidents. Got carried away with the MOH subject. The son is buried in Normandy next to his brother, Quentin, a WWl pilot killed in a dogfight with German pilots. Rumor had it that he was shot down by the Red Baron. Always denied by the RB. An amazing family that should be remembered this Veterans Day!

  50. Yes indeed–there’s Chub!

  51. Carmelo Pugliatti | November 18, 2016 at 5:48 pm |

    For me Bush is the preppiest (but i like JFK more).

  52. Carmelo Pugliatti | November 18, 2016 at 5:50 pm |

    Navy is more preppy/Ivy than Army or Air Force?

  53. Evan Everhart | March 12, 2018 at 4:28 pm |

    I prefer the nationalism of JFK to the Globalism of GHWB, but, based purely upon the points noted above, I must concur that GHWB is the “Most Preppy/Preppiest President”, his credentials are all in order, and his extremely old money WASP pedigree only serves to underscore the rest.

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