Words & Images from Preppy: Cultivating Ivy Style

Nine years ago Jeffrey Banks and Doria de La Chapelle presented me with a copy of their book, “Preppy: Cultivating Ivy Style.” It was an honor as a couple of my Q&As for Ivy Style are cited in the credits, as is W. David Marx’s article on the Miyuki-zoku, plus work from early Ivy Style contributor Deirdre Clemente.

While “Preppy: Cultivating Ivy Style” didn’t boast groundbreaking research, it’s a solid overview well timed for a new trend and new generation. Perhaps a quarter to a third of the book may seem extraneous (fashion writers, like literary scholars, feel they must cite sources they feel are related but which often feel tangential). However the bulk of it is devoted to precisely the origins of this style — prep and college students in the Northeast and the WASP establishment — while still taking an inclusive approach apropos for the year 2011. That may not entirely be the case nearly a decade later.

So here the authors with a terse summary of the style:

Preppy has always been acknowledged as an inherently American phenomenon, a fashion — or anti-fashion as some have called it — whose imagery perpetually connects us to idyllic college days, sport, and the spirit and vitality of youth. Preppy’s origins are rooted in the grounds of the elite Ivy League universities of the 1920s, where young, WASPy and wealthy gentlemen invented a relaxed new way for collegians to dress by co-opting athletic clothes form the playing fields, mixing them with genteel classics, and decking themselves out with caps, ties, pins and other regalia to signify membership in a prestigious club or sport. They then embellished the look with the best possible accessory: an air of complete and utter nonchalance.

But you can’t feign nonchalance until you nail the details:

In the elite, insular and often snobbish collegiate world, one’s identity was in the details: what a man wore, how his tie was tied, where his hair was parted and what club he joined were of paramount importance. Among the reasons behind Ivy League style’s resounding popularity with college students was the immense peer pressure to conform and its close relative, the deep need to belong.

And speaking of conformity, here’s Banks and de La Chappelle the Ivy heyday:

It didn’t take [postwar, college-educated men] long to learn that “working in corporate America demanded a knowledge of certain codes, many of which were embedded in the corporate uniform.” America had become more and more politically conservative, and Ivy League clothes — with their inherently understated quality and ability to blend in — were the perfect expression of the new “buttoned-down” philosophy. Ivy college graduates, well schooled in conformity, went to work uncomplainingly in their narrow-lapeled sack suits with skinny ties, while older alums, inspired by the slimmer, more youthful-seeming style, also joined the growing band of sack-suited men.

Some of the photos will be familiar, while others are fresh. Here is a handful of images I liked, which Rizzoli was kind enough to provide. Above is a scene from the film adaptation of Philip Roth’s “Goodbye, Columbus.” Below, Groton students, from the graduating class of ’67, in madras jackets:

More madras, with the classic pairing of white buttondown and solid tie. This is co-author de La Chappelle’s brother, Gary Martinelli:

And finally some more students at Groton. — CC

Images provided by Rizzoli. Photo credits: 1, The Everett Collection; 5, Corbis Images

52 Comments on "Words & Images from Preppy: Cultivating Ivy Style"

  1. Urban Haute Bourgeois | October 18, 2011 at 11:06 am |

    The photo entitled “More Deerfield Students” nails it. It’s like visual evidence of the Hegelian/Marxist dictum that each establishment has within it the seeds of its own destruction. WASP non-chalance is just so damned evident in this picture (I love the kid with the necktie turned around the wrong way and the droopy socks). But it’s the guy on the left with the sandals and socks lets the viewer know: And After Us, the Deluge.

    If this picture was not taken in 1965 or 1966, I will eat your Shaggy Dog sweater.

    It’s the end of WASPdom, but never did WASPdom look better.

  2. Urban Haute Bourgeois | October 18, 2011 at 11:09 am |

    Hold on to your sweater. Now that I look at it, I’ll say 1968. Like the peach at its sweetest. Rotting concurrently.

  3. WFB is a trad god. If you get a chance, check out the pics in his book “Atlantic High,” about one of his sailboat voyages. Legendary. (He has other sailing books too, and I’m sure they all feature outstanding shots, but “Atlantic” is the one I have at hand.)

  4. Simply mahvelous. Absolutely top drawer commentary!

  5. You guys are making me feel bad about my rather harsh (scathing?) review of the book.

  6. I was into this until you dropped the Buckley picture in there. It was like eating a delicious meal and then suddenly having someone come over and pee on your plate.

  7. that sandals and sox guy, bottom picture, far left, i think he turned out to be Lawrence Summers-jw

  8. Ulysses,

    Now you know how I feel when I see pictures of any of the Kennedys.

    Except that I don’t experience it in scatological terms.

  9. The Buckley picture is fantastic, and that is coming from a liberal Democrat!

  10. Does anybody find it odd that WFB was not from the East or from any branch of the Establishment, but he is accepted as an exemplar of preppiness, etc., while Christian can’t even write a blog post without getting called out as an imposter?

  11. Yes, the photos are great!
    Hey, is that Gore Vidal’s yacht behind
    pursuing at ramming speed!?!

  12. Button-Down Mind Strikes Back | October 22, 2011 at 5:13 pm |


    Ironically enough, the people who seem to obsessively attack CC as a “fake” are from LA or the UK. Go figure.

    Methinks some people are a bit insecure.

  13. I guess the Buckley picture gave me bad juju because he represents everything that’s historically awful about the ivy/trad lifestyle w/r/t/ classism, racism, sexism, etc. Those things need to be lived down, not celebrated.

    i like the clothes from an aesthetic perspective, but let’s not forgot that the politics that came with them were (and don’t forget still are) often downright vile.

  14. Ulysses, I think just as many lefties as righties wore and continue to wear tweed jackets, oxford-cloth buttondowns, rep ties, flannels and Weejuns.

  15. What Ulysses is saying is that having a point of view that is different from his own is unacceptable. He’s saying that the American nation as it historically existed was “downright vile.”

    Ulysses, your leftism, and its intolerance of all that is not of the left, is showing.

  16. @Christian: You’re statement above is accurate. But I think Ulysses is saying that Buckley specifically is an icon of the “righties” who wore the style, and Ulysses is accurate, I think, that Buckley stood for ideas that many people on the left, the center and the moderate right would find disturbing or worse. Still, I think that picture is fantastic and wish I wore my clothes with that much nonchalance.

    @Button-Down Mind Strikes Back: You, too, too make a good point that these knee-jerk critics of CC appear to be no more Eastern than he.

    @Henry: I don’t think Ulysses is saying that every view besides his own is unacceptable. I think he’s just saying he doesn’t like WFB’s politics. Lots of people don’t. It’s no big deal. I think Ulysses is merely making a personal statement about his own discomfort with WFB. I don’t think he requires you to agree with him. However, some things about American history are pretty “vile.” As good stewards of our nation, we can be candid and critical about how we think we can continue to improve. People all over the political spectrum want that.

  17. omg *Your. My high school grammar teacher is staring daggers at me right now!

  18. Gabe,

    With respect, I disagree, Ulysses is engaging in the all-too-common modern practice of reviling the actual, historical, existing America. He is identifying the people who are most representative of those who founded and built America with “classism, racism, sexism, etc.”

    This is unacceptable.

    Now, I grant you that America has suffered, to a greater or lesser extent, from those ills. This is as remarkable as saying that the sun rises in the east, because all societies everywhere and throughout history have “suffered” from these maladies. However, the modern leftist (who often calls himself a liberal, or, disingenuously, a “progressive”) believes that Western culture is uniquely guilty of these shortcomings, and that the only way to overcome them is to overthrow the guilty societies and replace them with something “better.”

    To limit myself to clothing alone, the Ivy style in its heyday was not the exclusive domain of the WASPs, but was, as has been well-documented here, worn by a broad swath of Americans, including blacks, and often influenced by Jewish clothiers. “Racist” and “classist” indeed! However, in our modern “enlightened” world, where most people have thrown off the allegedly oppressive yoke of The Man’s suit and tie, people have been released from decorum, and are free to wear sweats and flip-flops in public. They are free to bathe our eyes in the visual pollution of their guts hanging out from underneath their ad-festooned T-shirts, to assault our vision with their body piercings and facial tattoos. Improvement it is not.

    Unlike most, I believe that we can only achieve our highest potential when we suppress, not indulge, our every urge. Modest, tasteful clothing. clothes that demonstrate respect for others and whatever situation we find ourselves in, are far more conducive to this goal than our modern self-indulgent “aesthetic.”

  19. @Henry

    what a load of complete and utter bullshit…

  20. Henry,

    You speak too much,… and remove all doubt.

  21. J.,

    Welcome to the world of adult discourse! That is the first thing you’ve written here that manages to be critical without being gratuitously offensive. I hope you can continue with it.

  22. Lovely book. Fabulous photographs and great to study for style indicators for any one seeking to get the right twist in their wardrobe.

  23. Richard Meyer | January 18, 2012 at 4:20 am |

    I enjoy the old pictures a lot, but the Hilfiger ads and some of the new stuff not at all. “The Hilfigers”- yuck. The old Polo ads by Anthony Edgeworth were the best.

  24. I’ve been here for the last six months, so I’m still reading older articles. But, I must say reading the ill informed opinions of WFB are amusing. One wonders if any of them have met him , talked to him, or read any of his serious writings, I doubt it. WFB a catholic, with a liberal ivy league education, he rejected Rand, went to war with the Birchers, never tolerated racist and defended the rule of law in our constitutional republic. He always treated his adversaries on the left with respect, while usually intellectually skull fucking them.

  25. I see by some comments that some people need to learn that buying clothes does not make you Preppy.

  26. Vern Trotter | February 6, 2018 at 8:50 pm |


    What a great riposte; all of them.

  27. Vern Trotter | February 6, 2018 at 9:07 pm |

    My closest friend was friendly with Bill Buckley. Many of his witticisms were said tongue in cheek. Like a tattoo on the butt of AIDS victims or asking for a recount if he won the NYC mayoral race or annexing Israel. He was not ill informed about anything of which he published comments.

  28. For this repost — as many of the older posts need reformatting — I removed the now well known WFB picture and just stuck with the old black and whites.

    Only then did I see that he sparked much of the discussion in the comments….

  29. http://www.ivy-style.com/from-the-ends-of-the-earth-international-elements-of-the-ivy-preppy-wardrobe.html

    Above is a 2017 post which demonstrates that preppy/Ivy style is hardly an “inherently American phenomenon”. Preppy’s origins span the globe.

  30. MacMcConnell | November 24, 2020 at 2:10 pm |

    That’s my post above by MAC. I did get to meet WFB after a Firing Line filming in of all places Topeka, Kansas at Washburn University. He was a hoot to talk to, very dry humor. He in some ways reminded me of Bob Dole’s humor.

    The look was originated at Ivy League universities long ago, but it spread nationally after 1950. It’s how most of my cohorts dressed everywhere I’ve lived, Mississippi, Texas, Kansas and Missouri, at least in college towns and urban areas. I’m 69.

  31. That’s Ali McGaw (as Brenda Patimkin) and Richard Benjamin (as Neil Klugman) in photo up top from film version of Philip Roth’s novel “Goodbye Columbus.” In real life, she attended Wellesley, he Northwestern, and the author Bucknell. Not Ivy’s, but all darn good schools in their own right.

  32. Trevor Jones | November 24, 2020 at 5:22 pm |

    @Mitchell, it is inherently American, in part, because of its diverse, international background. It plucks items from all over the globe and puts them together in a cohesive style that makes sense — something only an American style could do. That’s not to say its origins don’t lie elsewhere (as with most everything in America), but the creature it became is most certainly American.

  33. @Trevor Jones

    Nothing is “inherently American” about preppy/Ivy Style. The equivalent in France, for example, is called “BCBG”. Lots of Lacoste polos (France), Barbour jackets (U.K.), and penny loafers (Norway).

    Speaking of polo (the sport, not the shirt), preppies from India were the inspiration for camel hair polo coats, polo sweaters (turtlenecks), and button-down shirts-which Brooks Brothers calls “the original polo shirt”.

  34. Nine years, wow. I remember meeting the authors at a book signing at J. McLaughlin on Charles Street in Boston before the shop was expanded. It’s definitely a snapshot of a time, Lilly Pulitzer was still alive and Rugby RL was open. A good photo book for reference.

  35. Trevor Jones | November 24, 2020 at 8:43 pm |

    @Mitchell, that’s like saying a Jaguar isn’t inherently British because automobiles were invented in Germany, not England. Just because something has it’s origins and influences from somewhere else doesn’t mean that it is then impossible for it to be part of the culture of that place.
    The Brits took the concept of an automobile and made a version that was very unique to them; the origins of the car are in Germany, but a Jaguar is undoubtedly British. The Americans took the concept of classic menswear, incorporating elements from the world over, and made a version — that included those eclectic elements and influences — that is uniquely American.

  36. Vern Trotter | November 25, 2020 at 2:36 am |

    A couple of comments here require correction:

    1) The above photo shown first is of Richard Benjamin with his wife, Paula Prentiss, not Ali McGraw. They sat in front of me at Fenway Park one summer.

    2) Most egregious is the comment that the great William F. Buckley Jr. was racist. All his positions and opinions came from his solid base of logic and facts. Any who knew him and most who did not will attest to this.

  37. @Berkeley Breathes:

    I beg to differ. Maybe you should read the comments from the post cited in the first comment above.

    Ivy/preppy style has never been an “inherently American” (or even British) phenomenon. It is a global phenomenon.

    Let’s take your example of the 3/2 jacket. This is a feature of the No. 1 sack suit sold by Brooks Brothers in its heyday. Is it
    “uniquely American”? No. The Neapolitans developed this style and became a part of the soft-shouldered “giaca (sp.?) Neapolitana”

    Case closed.

  38. Trevor Jones | November 25, 2020 at 8:25 am |

    @Mitchell, tea is not an integral part of British culture because it’s grown in Asia and drank all over the world.
    Wait a minute….

  39. @Trevor Jones:

    I’m not going to beat a dead horse, but I think we agree that the origins of Ivy/preppy style extend much further than the hallowed halls of academia.

    For his next book, I wish Mr. Chensvold would write a coffee table guide to international men’s fashion: “From the Ends of the Earth; International Elements of the Ivy/Preppy Wardrobe”. It could be part travel diary, and part guide to men’s fashion, kind of like Alan Flusser’s international men’s shopping guide at the end of “Style and the Man”, except with photos.

  40. Trevor Jones | November 25, 2020 at 9:45 am |

    @Mitchell, not sure where academia came into it. That was never in question. The question was whether Ivy is inherently American, which it is, the same way tea is inherently part of British culture.

  41. @ Berkley Breathes

    Thank you for the link making it clear where Buckley stood. Regardless of the apologists muttering that he was of his time, you have done a useful job in emphasising that there is more to a man than a button-down collar.

  42. Well, if it was published in The Intercept it just has to be true.


  43. @ sacksuit

    What are you implying?

    Buckley’s editorial, ‘Why the South Must Prevail’ is downloadable.

  44. I said it must be true.


  45. Buckley’s views on many things, including race changed over the years. Belief systems do not exist in a vacuum. Intelligent people evolve.

    “When the conservative editor and intellectual William F. Buckley, Jr., ran for mayor of New York in 1965, he may have been the first conservative to endorse affirmative action, or, as he called it, “the kind of special treatment [of African Americans] that might make up for centuries of oppression.” He also promised to crack down on labor unions that discriminated against minorities, a cause even his liberal opponents were unwilling to embrace.”

  46. In our recent post on poets, I said I’d like to get back to writing poetry. Well here’s one:

    It is unacceptable
    To have ever held
    An unacceptable view
    However true
    And this means you

  47. @Berkeley, believe or not it’s possible to admire a person’s style without agreeing with their politics. Your apparent distain for Buckley has seemingly blinded you to this fact. I’m not quite sure why you would conflate those two topics into one post though.

    I will agree with you that Buckley was complex. I certainly didn’t agree with all of his views.

    Joe Biden was complicit in passing legislation responsible for putting non violent drug offenders in jail for a very long time; a disproportionate amount of them young black men.
    I don’t agree with much of Biden’s political ideology, but I voted for him; the first democrat I have ever voted for in my life. I am not a young man. Life is messy.

    Happy Thanksgiving

  48. Curious the attempt to gin up a calumny on bigotry of WFB on this site. I would guess the vast majority of readers here could care less about him. But I imagine that is true everywhere. One’s efforts would be better rewarded, say, by trying the subject on Abraham Lincoln, the Roosevelt’s, (FDR and Eleanor) and of course there is always Woodrow Wilson, if the subject has not been exhausted there.

    Ernest van den Haag was kept around by Bill because he was a former communist operative, not because he was a bigot. He could have found those anywhere. Likely also for some of the same reasons he (EvdH) was on the faculty for decades at Fordham Law, State University of New York, NYU, The New School, others.

    Bill had noted for years that he and his magazine had been wrong about civil rights in earlier days. “ People who are otherwise good, and even whole societies, can be wrong about matters of moral import. …. A few…have implied that hostility to the aspirations of American blacks was one of his animating impulses, which is a CALUMNY.” —NR Obit Edition, March 24, 2008.

    Abraham Lincoln, the Roosevelts, (FDR and Eleanor) and always there is of course Woodrow Wilson.

  49. Vern Trotter | November 28, 2020 at 7:40 pm |

    Like wrangles with an old girlfriend of mine, I forget what exactly was the point. At least the back and forth has not degenerated into churlishness as sometimes happens here. Enjoyed the discourse.

    Oh, add LBJ to my list. A more classic bigot would be hard to find and he was a killer too; his own sister and his boss, a sitting president, done in by hit men, now alleged by several.

  50. Henry Contestwinner | December 2, 2020 at 7:53 pm |

    Yeah, that Buckley guy sure showed of his raaaaycist bona fides by having people such as Noam Chomsky, Milton Friedman, Allen Ginsburg, Jesse Jackson, Vernon Jordan, Henry Kissinger, Huey Newton, Thomas Sowell, and Walter Williams (RIP) as guests on his show.

    Criminy. There seems to be no shorter route to the complete extinguishing of all critical thinking than the application of the sub-moronic racist epithet.

  51. Vern Trotter | December 5, 2020 at 4:51 pm |

    His show, Firing Line, ran for 33 years and over 1500 episodes. The longest in TV history at the time if not still. Nary a charge of bias.

  52. Vern Trotter | November 25, 2020 at 2:36 am |

    Nothing here needs correction. Richard Benjamin must have been cheating on wife Paul Prentiss with his “Goodbye Columbus” co-star Ali McGraw at Fenway that day.

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