Jack and John: The Sartorial Dichotomy of JFK

Was John F. Kennedy the most Ivy of US presidents, or did the most important man in the country actually encourage American men not to follow the Ivy League Look?

That depends on whether you’re talking about President Kennedy the nation’s leader, or Jack Kennedy relaxing among friends and family in Hyannis Port.

On assignment for the latest issue of The Rake, I examined the split between Kennedy’s public and private life, and how this was reflected in his wardrobe.

The text of the article is below, or you can download a printable PDF.

Setting the President: John F. Kennedy’s dress sense was central to his public persona, forming no small part of this truly modern president’s enduring iconography
By Christian Chensvold
The Rake, Issue 7

Photographs of John F. Kennedy generally fall into two categories. In the first, we see him at his family’s Cape Cod retreat, sleeves rolled up, wearing khakis grass-stained from touch football, or clad in Nantucket Reds and sunglasses sailing the sea. In the second, his presidential kit, we see another man altogether. Kennedy’s dark suits hang with a certain awkwardness, the shoulders large and high, his two chest buttons both fastened.

Though both are equally iconic, these two images of JFK reveal the sartorial differences between the man’s public and private lives. Privately he was the Choate and Harvard-educated scion of a patrician American dynasty, while publicly he was a progressive young Democrat, commander on the frontlines of the Cold War, and careful crafter of a public image in the new age of television.

This schism makes JFK both the ultimate preppy president — his administration reigned at the height of the Ivy League Look — and an ironic hastener of the look’s decline, undermining the very style he so perfectly embodied. Though Kennedy could hide neither his Catholic faith nor brahmin accent, this first great image crafter of the TV age could strengthen his broad appeal with two sartorial gestures: He would wear two-button suits instead of three-button sack models, and he would eschew buttondown collars. The result, noted LIFE Magazine in 1961, was that the president’s clothes “fail to conform to current Ivy League fashion.”


Before becoming a style setter, Kennedy started out as a ragamuffin. “As a young man he was notorious for his personal disorder,” writes Neil Steinberg in “Hatless Jack: The President, the Fedora, and the History of American Style.” “His boarding-school roommates complained of his messiness, particularly with clothes. He would show up with his shirt untucked, or without socks, or wearing a rag of a necktie.”

Before his marriage to Jacqueline Bouvier in 1953, “Kennedy had been a sloppy dresser who favored baggy suits, clashing shirts and ties, and ratty tennis shoes,” according to historian Thurston Clarke.

With Jackie’s guidance, Kennedy’s style evolved into a paragon of simplicity and understatement. His casual weekend mufti was collegiate and Northeastern — Shetland crewnecks, penny loafers sans socks, white t-shirts, polo shirts and chinos, with a notable absence of pattern. His suits were solids or light stripes, shirts almost always white with a short straight collar, his ties discrete reps and clubs. Like Steve McQueen, another charismatic public figure with subdued taste, Kennedy gave his clothes style, rather than the other way around, a testament to the idea that clothes should never upstage their wearer.

Sartorial simplicity suited Kennedy best because he had star quality, an air of innate dignity, recalled his physician Janet Travell, “that was the product of personal reserve, self-respect, style and a distaste for ostentation.” But there was something else. With his sunglasses and convertibles, ironic wit and military heroics, Kennedy had something no American leader had ever had before: cool.

Much of Kennedy’s cool came from his hair, a Samson’s mane of potent charisma and something Kennedy famously avoided covering with headwear. “In a hat he looked far older and almost unrecognizably ugly,” writes Steinberg. “And he knew it.”

Kennedy’s effect on American taste was palpable. “Kennedy sets the style, taste and temper of Washington,” wrote GQ in 1961. “Cigar sales have soared (Jack smokes them). Hat sales have fallen (Jack does not wear them). Dark suits, well shined shoes, avoid button down shirts (Jack says they are out of style).”

As GQ points out, Kennedy set styles as much for what he negated as for what he advocated, and he stood in favor of two-button suits as much as he stood against buttondown collars. Historians have suggested that Kennedy preferred two-button suits because they better accommodated his back brace. Paul Winston, however, who made suits for Kennedy while working at his family’s legendary clothing company Chipp, recalls Kennedy wearing a brace during fittings at New York’s Carlyle Hotel, but says the button stance would not have mattered.

What is more likely is that Kennedy felt that while he couldn’t hide his privileged background in a television age that required mainstream appeal, he could at least obviate his image sartorially by wearing suits less redolent of the Eastern Elite and more becoming a man in the limelight of international affairs. When asked if suits for the newly elected president would be two-button, tailor Sam Harris said, “Certainly, two button. We don’t follow Ivy League or beatniks. We make gentlemen’s clothes.”

And when it came to shirt collars, Kennedy mocked his brother Robert in the press, telling LIFE, “He’s still wearing button-down shirts; they went out at least three years ago,” and told friend and confidant Paul Fay that his button-down collars were “too Ivy League.”

Privately preppy, publicly the leader of the free world, Kennedy was always an icon. But in the annals of sartorial history, JFK is less an example of a well dressed man than a man with tremendous charisma, and for such men understatement is always the best frame.

“Kennedy was a handsome and important man,” remembers Paul Winston. “That old saying that clothes makes the man? Not really. I think the man makes the clothing.”

Images from Time magazine’s “JFK Style.”

This article originally posted in February 2010.

27 Comments on "Jack and John: The Sartorial Dichotomy of JFK"

  1. Ralph Kinney Bennett | February 3, 2010 at 5:58 pm |

    Interesting stuff, Christian; nicely done. I’ve always found it interesting that a lot of people, who didn’t really pay attention to the finer points of the Ivy look, did not perceive the dichotomy you discuss here. They always thought of Kennedy as Ivy in style, despite the two-button suits. I can recall many people remarking on John Kennedy’s “Ivyness.”

    I had the opportunity, as a journalist to meet both the brothers, Bobby and Teddy, and I was struck by how each of the three men dressed differently, as if they were consciously or unconsciously wanting to differentiate themselves from each other. Bobby, was obviously the most rigorously Ivy. John departed from that, but not completely and there was always a vestigial whiff of the Ivy about him, which probably accounts for that perception by the “unknowing” mentioned above. Teddy made the biggest departure from the old establishment norm and from the style of his brothers. I often saw him on Capitol Hill and often noted to myself this sartorial departure (although he would occasionally pull himself together, so to speak, with a conservative navy suit and rep tie). It seemed that with each of his many bouts with his waistline his clothing tastes became more and more what I would call non-descript conventional.

    Kennedy somehow made everybody who preceded him look old or at least old- fashioned. Not to get into a chicken and egg thing, but somewhere, somehow this manifested itself in “style” becoming an issue to be observed and dissected in the press as never before. Study the old photographs of Roosevelt and they are a clinic in establishment style. Truman got razzed some for his Hawaiian shirts but he was extremely attentive to his appearance (he was partner in a men’s store, for crying out loud!) and his crisp white shirts, tightly knotted ties and impeccable double-breasted suits always projected well in a conservative mid-western way. Ike’s single and double-breasted suits were for the most part well done and gave him an authoritative look that didn’t completely register with a public whose lasting image of him was in his General’s uniform. (The paragon, to me, of Ivy/establishment style when out of uniform was General George C. Marshall, who always looked “to the manner born” in his suits, tweed sport coats and even his most casual clothes). But these things didn’t seem to matter much with press and public. It was just a given that public figures would dress properly. That changed with Kennedy I can still remember (I was in college) being rather stunned to see a little piece in Esquire regarding the cut of President Kennedy’s suits, replete with close-up photos of the details. It was very unusual at the time. Well. I guess that’s more than you wanted to hear about that! Anyway, great piece, Christian.

  2. Thanks for the kind words, Ralph, as well as for taking the time to leave such a great response. Interesting you say that Bobby was the most Ivy; Paul Winston says that while at Chipp he mainly worked with Bobby.

  3. Jackbenimble | February 4, 2010 at 1:24 pm |

    I love this piece CC. And RKB is right about Teddy – who having lived the longest – eventually adopted the contemporary globalized-politician look favored by President Obama, Tony Blair and best done by President Clinton (post-presidency) and President Sarkozy. In some ways he perhaps followed in President Kennedy’s footsteps in this way, as he attempted to conform to modern tastes publicly and kept his less-democratic kit for moments of leisure. With family & friends he was far more likely to trot out faded navy tennis shirts and rumpled khakis – especially at the helm of the Mya.

  4. Excellent post, as always.

  5. Great article, but the doctored photos that accompanied it are a bit much for my taste… especially the glaringly large Polo pony on Jack’s formerly plain blue pullover.

  6. I was waiting for someone to point that out.

  7. Great article Christian, though I disagree with your statement that JFK had a brahmin accent. His accent cannot be labeled brahmin, nor can it be described as Boston English (the accent of the working class). It is distinct to the Kennedy clan and perhaps fittingly, as they represent the reconciliation between Irish Catholics and the American aristocracy.

  8. Interesting, Lane, and thanks for the correction.

  9. Jack Gormley | February 9, 2010 at 5:57 pm |

    Fascinating article, Christian.

    I read somewhere years ago that JFK only (reluctantly) gave up button-down collars when Jackie Bouvier (sic) told him they looked sophomoric and unprofessional. Did you come across anything along these lines in your research?

    Thanks for a great read!

  10. Thanks, Jack.

    Didn’t come across that Jackie anecdote; if I had, it would’ve been in there.

  11. Evidently Harry Winston in New York made JFK’s suits. His son still operates the business. I read somewhere that he threw out the patterns that his father had made for JFK after his death and now regrets it big time. I imagine so

    Any comments on this?

  12. See here:


    Harry Winston may have made things for JFK, but they wouldn’t have been suits.

  13. Bud Rupert | May 26, 2011 at 1:38 pm |

    Well, when I spoke with Paul Winston he said his father did indeed make his suitings. If you have other information please share.

  14. I always wondered if JFK was really 6 feet tall. I saw where his measurements for his suits were 34 inch sleeves, which seems too long. His waist was a 32, which seems about right for a man his weight. Any info on his suit stats?

  15. Only one thing wrong with the article — Jack did not have a Brahmin accent. Anyone from Boston could tell you he was obviously either from Dorcester or Milton, just by listening to him. I grew listening to Ted Kennedy giving speeches, and he was proud of that accent — but he’d roll over in his grave if you accused him of having an Irish-hating, anti-busing, Beacon Hill republican accent.

  16. Christian | July 28, 2011 at 8:21 pm |

    Leave it to a Californian transplanted in New York to mess that one up.

    But what do Brahmins have against busses? Surely the poor must get around somehow.

  17. Christian- the “busing” issue that E.B. was referring to was opposition in Boston to integration of Boston-area schools in predominantly white areas with black students.

    E.B – Beacon Hill…Republican?!?! Hah! No way. Elitist, moneyed Democrat “progressives” who probably supported the school integration [long overdue, anyways]. Didn’t really matter to them in any event- their kids went to Milton Academy or Choate. And anti-Irish? Wow- that was a LONG time ago [about 100 years] in Boston and definitely overhyped in service to the myth of Camelot.

  18. Anyone know where Jack kennedy got his shirts made?

  19. karl anglin | January 24, 2013 at 5:16 pm |

    JFK had his shirts made by Charvet in Paris ,France.
    He would then have the labels cut out of the shirts.

  20. In the PDF of this article, there’s a picture of Jack with Caroline and he seems to be wearing a navy Polo zip-up. If you look at other pictures, he’s clearly wearing a plain, shawl collar cardigan that’s probably not from Ralph Lauren. The zip and Polo logo were clearly photoshopped into the picture. What gives?

  21. Read the captions of the photos. The Rake put modern clothes on the vintage photos.

  22. I’ve read articles in the past that said JFK preferred the English drape style and once had the chance to ask Paul Winston about this. Paul said that Kennedy’s suits were simply a more highly fitted version of the standard Chipp suit. A lot of people point out that Kennedy preferred a 2 button stance, but in reality there’s very little difference between a 2 button stance and a 3 Roll 2 (the standard Ivy League look). The lapel roll is the same, you just don’t have the unused button and buttonhole showing.

  23. All those modern clothes they put on JFK look awful, but I don’t think it was done so as to show us that clothes were nicer in the past.

  24. E.B. is absolutely correct. Kennedy’s was definitely not a Brahmin accent. And I certainly wouldn’t call him patrician either. Not in Boston or any other northeast city. The family was more generally dubbed ‘lace curtain Irish’.

    “And this is good old Boston,
    The home of the bean and the cod,
    Where the Lowells talk only to Cabots,
    And the Cabots talk only to God.”

    On the bussing question, please look up Louise Day Hicks.

    A salesman at Brooks once told me that their slim, two button Fitzgerald fit was named for JFK. That’s the only time I have heard that. Does anyone know if it is true?

  25. Poem for the day:

    President JFK
    In a 1960
    Mercury Monterey

  26. Vern Trotter | November 16, 2016 at 3:52 pm |

    “Lace curtain Irish.” In West Roxbury, they were known as “Two toilet Irish.”

  27. aquitaine | May 11, 2017 at 6:17 pm |

    Anyone know why Kennedy invariably and incorrectly worre his suit jackets with both buttons done up ?
    Here in UK/France this is considered rather uncouth & naff. I admire and like Ivy league style sack sports coats & suit jackets and, as we all know, they are buttoned up at the second (effectively top) button only.

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