Trinity’s Preppy Culture Defined

Trinity College Chapel on Reunion Weekend 2024

by Matthew Longcore, Trinity class of ’94

This article originally appeared in the December 7, 2010 issue of The Trinity Tripod.

It is official: Trinity is the preppiest college in New England. This proclamation was made by none other than Lisa Birnbach, author of the 1980 tongue-in-cheek bestseller The Official Preppy Handbook and co-author (with Chip Kidd) of the recently released follow up, True Prep. In the original Preppy Handbook, Trinity was listed among the top 20 preppy colleges in America. For True Prep, however, Birnbach decided not to create such a list, instead giving Hampden-Sydney College in Virginia the honor of being “the preppiest in America.” When yours truly asked Lisa on the Facebook fan page for True Prep why Trinity was not accorded this honor, she replied: “I have to stand by my decision. I’m willing to say that Trinity is the preppiest school in New England. For a small college, Trinity alumni are EVERYWHERE.”

The Pipes, Trinity’s oldest a capella group, formed in 1938. The group started as a quartet of four St. Anthony Hall brothers and by the mid-1960s had implemented instruments into their performances. Encyclopedia Trinitiana

Birnbach later validated Trinity’s preppy status at an event held at the New Canaan Library in the preppy hamlet of Fairfield County, Connecticut. This event included a fashion show featuring clothes from the super preppy brand J. McLaughlin. When asked (again by yours truly) if she was willing to stand by her Facebook proclamation, Birnbach replied that yes, indeed, Trinity is the preppiest college in New England. She described Trinity as “a hot school that everyone wants to go to.”

Montage of album covers. Photo credit: Watkinson Library – Virtual Museum. Encyclopedia Trinitania

Trinity’s longstanding reputation as a preppy school predates the Preppy Handbook by many years. In 1963, Gene Hawes published an article in the Saturday Review titled “The Colleges of America’s Upper Class” in which he provided statistical data about the alma maters of men listed in the Social Register. Trinity came in fifth place behind Yale, Harvard, Princeton, and Pennsylvania but well ahead of much larger institutions such as Brown, Columbia, Cornell, and Dartmouth. This article was published in what is now known as “the Mad Men era” when Trinity and several of the Ivy League schools were still all-male bastions. A decade later, coeducation had swept Trinity and its peers.

Trinity College Women’s Rowing

By the 1970s, a fictional Trinity preppy made his silver screen debut (albeit a brief cameo appearance) in the movie Jaws. In the opening sequence of the film, the male character Cassidy (dressed in a blue oxford button down shirt and khakis) mentions that he attends Trinity. When police chief asks, “Do you live here?” (“here” being the preppy summer resort of Martha’s Vineyard) Cassidy replies, “Na, Hartford, I go to Trinity. My folks live in Greenwich.” Greenwich, as preppies know well, is very preppy indeed.

The Trinity Ivy is the college’s student-run yearbook published from 1873 to 2019.

Fast forward to 1980 and by this time Trinity men and women had earned their rightful place in The Official Preppy Handbook, which describes the student body as follows: “Universally Preppier, students here embody good-looking devil-may-care-ism.” The “Fraternal Instincts” section of the Preppy Handbook also seems Trinity-inspired in its description of Greek life on preppy campuses: “There are some nationally established Preppy frats, where most of the members are from Darien and almost all went to Prep school in Massachusetts – Psi U and St. Anthony Hall fit this mold most consistently.”

Built in 1878, St. Anthony Hall is the house of the Epsilon Chapter of Delta Psi fraternity. Encyclopedia Trinitiana

The Preppy Handbook’s list of the top 20 preppy colleges in America includes over half of the 11 schools of the NESCAC (Amherst, Colby, Connecticut College, Hamilton, Trinity, and Williams) but only one member (Princeton) of the eight schools in the Ivy League, despite the public perception of the Ivies as “the preppiest” of schools. The logic behind this is explained in a section called “The Ivy League Dilemma” which states that “the pink-and-green scale tips in favor of the more homogeneous smaller schools.” Tailgate culture at preppy colleges, in which the actual game is ignored in favor of socializing over Bloodies and Whiskey Sours, is also described in the Preppy Handbook. The “Discovering Prep” section of the book highlights “some crucial points of the Prep Ethos” which include favoring “fake college football (Williams vs. Amherst)” as opposed to “real college football (Michigan vs. Ohio State).”

Trinity College rower John Graves. Rowing Blazers

Trinity’s preppy reputation has endured into the 21st century. A 2007 article in The New York Times titled “Pink Shirts Welcome” describes the uber-preppy crowd at Bar Martignetti in Manhattan’s SoHo district. The article quotes the bar’s owner, Trinity alumnus Anthony Martignetti ’02, as stating, “I went to Trinity, which is the epicenter of preppy partying in the Northeast.” The Insider’s Guide to the Colleges, which is published annually by The Yale Daily News, includes Trinity on its “Top Ten Preppiest Student Bodies” list along with such schools as Princeton and UVA. In June of this year, The Huffington Post published a similar list – the “Top Ten Preppy Colleges” – and once again Trinity made the cut, coming in at a respectable #3 behind #2 Princeton and…yup, you guessed it, #1 Hampden-Sydney College.

Downes Memorial Clock Tower

Though the Bantams lost out to Hampden-Sydney as “America’s preppiest college” in True Prep, Trinity College is actually mentioned several times in the book. Two of the fictitious preps featured in the books are described as Trinity graduates: English teacher “Mrs. Radcliffe” (page 66) and well-dressed post-grad “Anderson Flatto” (page 112). Among the many elements of Anderson’s preppy wardrobe is a CK Bradley embroidered belt which holds up his cords embroidered with whales. CK Bradley, as many Trinity preps know, is a preppy brand of clothing designed by Trinity alumna Camilla Bradley ’99, who started the line during her college years by making ribbon belts for her classmates. True Prep concludes with a timeline of preppy-related events which have taken place in the last 30 years since the publication of The Official Preppy Handbook. Trinity is mentioned twice in this chronology. The first mention is the February 21, 2010 victory of the Trinity men’s squash team which marked the team’s 12th consecutive national championship. According to True Prep, team members were “compared to preppy rock stars.” The second mention in the timeline is September 2, 2010 when the “full-time, First-year students’ meal plan begins with dinner at Trinity College.” Why exactly this particular date is mentioned, no one but the authors can know for sure.

Trinity College rowing blazer on display at The Andover Shop

10 Comments on "Trinity’s Preppy Culture Defined"

  1. The post was both interesting and well-written, in my opinion. Much obliged for the excellent material!

  2. Trinity College is among the preppiest of all schools that preppy students attend. There is much for the fan of prep style to enjoy, from clothing to architecture and beyond. If there is a college that preppy fans enjoy, it is sure to be Trinity.

  3. Richard E. Press | July 29, 2024 at 8:57 am |

    Alumnus Tucker Carlson candidate for Trinity Prep Hall of Fame?

    • Matthew Longcore | July 29, 2024 at 4:58 pm |

      Trinity Prep Hall of Fame would include Julia Hoyt Amory (founder of clothing line Julia Amory), Katherine Gage Boulud (brand ambassador at The Dinex Group – Daniel Boulud), Camilla Kerr Bradley (founder of clothing line CK Bradley), Lily Baker Hottensen (travel operations at Indagare), and George F. Will (Pulitzer Prize winning writer).

    • Didn’t know that. I remember seeing a picture of him wearing a tweed jacket smoking a cigar on this site. Good stuff.

  4. whiskeydent | July 29, 2024 at 10:46 am |

    I’m doing my best to get over my dislike for the term preppy. The G&T’s help.

    • I gave up trying to “get over the dislike.” Too much effort. I still much, much prefer “Natural Shoulder(ed)” in reference to the style in general, and “Ivy” on occasion when talking specifics.

  5. Hardbopper | July 29, 2024 at 3:01 pm |

    Great read, thanks. “We” need to make Men’s Glee Clubs great again. The Women’s Rowing Team looks terrific.

  6. Interesting. I’m well familiar with Trinity (campus, vibes, several alums). There is a vibe to/of/about the place, to be sure — difficult to describe. Very “Vineyard Vines” and “pipeline-to-Wall Street” (and eventually private equity). Not necessarily a criticism, but certainly distinct from (even dissimilar to) the more genteel, patrician(ish) college cultures like Washington & Lee, Rhodes, Sewanee, Elon, Furman, and Davidson, where, a friend correctly observes, “Southern Democrats abide.” University of Richmond and Wake Forest have become so obsessively pre-professional (not unlike Duke and Vandy) that courtly, polished gentility has been, well, lost. Or, more accurately, intentionally discarded.

    If Mr. Press is astute in calling to attention to Mr. Carlson as a primary ambassador for Trinity, then, as something of a counterpoint, I’ll suggest the great Linwood Holton as the embodiment of an equally gracious-and-graceful Southern couth — still alive-and-well at W&L.

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