The Philosophy of Style by Christian Chensvold

by Matthew Longcore

Ivy-Style.com founder Christian Chensvold has published a marvelous book that is a must-read for anyone who follows this page. I was pleased to discover the book at the J. Press store in Manhattan when I visited in the spring for the J. Press Icons campaign. Little did I know then that I would have the opportunity to write about the book as the new editor and publisher of this site.

In case you missed it, The Philosophy of Style is a collection of Chensvold’s finest essays. As suggested by the title, the book has a scholarly tone, and this aspect of Chensvold’s erudite writing is certainly what initially drew so many of us to Ivy-Style.com in the first place. I, for one, have been following this page since its inception. My journey through a Ph.D. program in the humanities has delved into philosophy, history, and sociology, and anthropology. Chensvold’s writing features all of this. He is at once philosophical, historical, sociological, and anthropological in his analysis of classic menswear and gentlemanly style.

If one were to teach an introductory college course on the Ivy League Look, The Philosophy of Style would surely be required reading on the syllabus, along with Take Ivy and The Official Preppy Handbook. My version of such a syllabus would include sociologist E. Digby Baltzell (The Protestant Establishment, Sporting Gentlemen), novelist F. Scott Fitzgerald (This Side of Paradise, The Great Gatsby, and photographer Slim Aarons (A Wonderful Time, Once Upon A Time). Social historians including Cleveland Amory (The Last Resorts, Who Killed Society?), Stephen Higley (The Right People, The Right Places), Nelson W. Aldrich, Jr. (Old Money, Tommy Hitchcock), and Paul Fussell (Class, Caste Marks) would also be on the list.

The final group of authors – each with a focus on clothing – would include G. Bruce Boyer (Elegance, Eminently Suitable, True Style), Maggie Bullock (Kingdom of Prep), Alan Flusser (Clothes and the Man, Style and the Man, Dressing the Man), Richard Press (Threading the Needle books I & II), the podcast from Avery Trufelman (American Ivy), and of course, the collected works of Christian Chensvold.

The Philosophy of Style contains several of Chensvold’s best essays. Perhaps his most important contribution, and my personal favorite, is the essay titled “The Rise and Fall of the Ivy League Look.” Chensvold originally posted his 9,000-word essay in 2013, and then reposted it on Ivy-Style in 2020. Alan Flusser considers this essay to be the definitive history of the Ivy League Look, and quotes from it in his biography of Ralph Lauren.

Chensvold’s book opens with “Soft Shoulders and Hard Bop” and a terrific description of high society as it was in the mid-twentieth century:

“Half a century ago, a certain social set really had its priorities in order. Life’s pursuits ran something like this: Jazz, tennis, newspapers, Yankees vs. Red Sox, Newport and Nantucket, sailing, contemporary literature, prize fights, prep schools and the Ivy League, cigarettes and cocktails, college football, Broadway shows, and New York parties that blended socialites with beatniks.” (Chensvold 2023, 19)

Muffy Aldrich of Salt Water New England has correctly described this social set as “The Thing Before Preppy”:

“For me, the origin of the style is in the 1950s, around the coast of Connecticut. A culture was codifying influenced by the wealth and access of New York; strong schools; and the culture of so many early settled New England towns with deep British roots. The clothes were often bright and casual but still substantive and well made, much of which came directly from nearby manufacturers. Towns also had shops that specialized in imported Irish woollens and tweed.” (Aldrich 2021)

Chensvold and Aldrich are both spot on. They are describing a bygone era – the generation of people like my Ivy League educated grandparents. This generation lived in places like the North Shore of Boston, the Main Line of Philadelphia, and Fairfield County, Connecticut. My grandfather, a Harvard MBA who came to Connecticut in the 1950s and commuted from his home in Westport to his office in Manhattan, spent his summers sailing on Long Island Sound. Many of us who love the Ivy League Look are nostalgic for these halcyon days.

After painting a general picture of mid-twentieth century Ivy League society, Chensvold continues in the scholarly vein of an ethnographer and a historian:

“The social history of clothing is an elusive topic, forcing the writer into the anthropological role of outside observers, removed in both space and time as he attempts to chronicle the customs of a closed caste. Nowhere is this more apparent than in charting the dress of the American Protestant Establishment in the years before preppy style became a mainstream commodity.” (Chensvold 2023, 27)

The Protestant Establishment is a phrase borrowed from sociologist E. Digby Baltzell, whose book The Protestant Establishment: Aristocracy and Caste in America was first published in 1964. Baltzell popularized the acronym WASP, a term that Chensvold also references several times in The Philosophy of Style. According to Chensvold, “the particular use of color expressed by the WASP establishment seems to have originated, or at least been codified, in the postwar heyday of the Ivy League Look, emanating from a combination of resorts, country clubs, and college campuses up and down the eastern seaboard.” (Chensvold 2023, 27)

Color makes its way into menswear thanks to the Palm Beach look of the 1930s, the iconic pink Oxford cloth button down shirt from Brooks Brothers and Nantucket Reds from Murray’s Toggery Shop “indicating years of summers spent sailing.” (Chensvold 2023, 34) Madras is the ultimate expression of Ivy colorfulness and was the right choice for the for cover of The Official Preppy Handbook. The female corollary to this, of course, is Lilly Pulitzer, the brand which firmly established hot pink and lime green as the unofficial color combination for the preppy woman.

Chensvold returns to the topic of Brooks Brothers versus J. Press:

“Brooks Brothers’ smaller rival J. Press was a purer Ivy retailer in that it offered a broader selection (such as campus-oriented tweeds) within narrower perimeters. Brooks Brothers was Ivy and much more; J. Press was strictly Ivy.” (Chensvold 2023, 53)

This sentiment is echoed by The Official Preppy Handbook which describes Brooks Brothers as “the Oldest Preppy Store Still Alive” and J. Press as a store catering to “the ultra-conservatives of the old guard.” While Brooks Brothers became associated with businessmen working in New York or Boston, J. Press was more of a collegiate store with only a handful of stores next to Ivy League campuses. The J. Press stores located in New Haven near the Yale campus and at the Yale Club of New York City remain hallowed ground for Ivy style to this day.

As Chensvold writes, “New Haven is the top candidate for Ivy’s spiritual home.” (Chensvold 2023, 58) Princeton, however, may in fact be the true originator of the Ivy League Look. An article in LIFE Magazine from 1938 titled “Princeton Boys Dress in Uniform” established Princeton as the style leaders of America. Another article from the 1930s, written by Arthur van Vlissingen for The Saturday Evening Post, credited the resort towns of Newport and Palm Beach (the first two Brooks Brothers locations outside of New York) and the campus of Princeton as the epicenters of style. Here is his breakdown of the Big Three of the Ivy League:

“Harvard is a very large university in a great city which influences the student’s styles heavily…Yale is more compact and more finicky, but New Haven is also a large city. Princeton is a smaller town, off by itself where is can incubate a style effectively. Practically every Princeton student is well-dressed, whereas only one-third or so of the Yale men can qualify by our standards.” (Chensvold 2023, 62)

Chensvold continues this line of collegiate analysis by describing the lack of Ivy style at Columbia University:

“For despite its location in the city of Brooks Brothers, Columbia is seldom if ever mentioned for style reasons. As a commuter school, Columbia’s student body differed from the other schools, but one can also conclude that a certain amount of distance from the metropolis was necessary for the styling side of the Ivy League look to flourish.” (Chensvold 2023, 63)

This line of reasoning makes perfect sense, and has been echoed by F. Scott Fitzgerald, E. Digby Baltzell, and Lisa Birnbach.

This Side of Paradise, the first novel from F. Scott Fitzgerald who was a member of the Princeton class of 1917, compares the Big Three of the Ivy League as follows:

“I want to go to Princeton…I don’t know why, but I think of all Harvard men as sissies, like I used to be, and all Yale men as wearing big blue sweaters and smoking pipes…I think of Princeton as being lazy and good-looking and aristocratic—you know, like a spring day. Harvard seems sort of indoors.” (Fitzgerald 1920)

In The Protestant Establishment Revisited, Baltzell writes, “By the turn of the (twentieth) century, the college of New Jersey, which had recently changed its name to Princeton was far more homogeneously upper class than Yale…In contrast to Princeton, and even Yale, Harvard has always been guided by the ideal of diversity.” (Baltzell 1987, 131-132)

The Official Preppy Handbook provides a list of the top twenty preppy schools. Princeton is the only Ivy League university among the ancient eight to make this list. Regardless of the percentage of prep school educated students at Princeton, according to the handbook, “By graduation it feels more like 100%.” Columbia is relegated to the “Out of the League” list for having a distinctly anti-preppy culture. The handbook also lists over half (Amherst, Colby, Connecticut College, Hamilton, Trinity, and Williams) of the eleven schools in the New England Small College Athletic Conference (NESCAC). The handbook also features a section titled “The Ivy League Dilemma” which states that “the pink-and-green scale tips in favor of the more homogeneous smaller schools.”

So we are left with the world of the Ivy League Look as a something of a continuum. Small campus haberdashers like J. Press and The Andover Shop are more exclusively Ivy than large urban retailers like Brooks Brothers and J. Crew, which are Ivy plus a whole lot more. Similarly, smaller schools like Trinity and Princeton which focus on teaching a residential population of undergraduates are more homogeneously preppy than larger urban universities like Columbia and Penn which educate commuter students and focus on graduate education and research.

In the fourth chapter of his book, Chensvold ponders the Anglo-American concept of the gentleman:

“The notion that it takes three generations to make a gentleman is clearly an American one. Only a culture bred from democracy and capitalism would suggest that this lofty moniker does not require a hereditary title and a fox-hunting outfit. The difference between the English and the American gentleman is one of being vs. one of becoming. However, even in America, a country built by the self-made man, it is understood that one doesn’t become a gentlemen, to borrow from another adage, merely through one good guess on the stock market.” (Chensvold 2023, 111)

E. Digby Baltzell – perhaps the only sociologist to use the term “gentlemen” in the title of two books (Philadelphia Gentlemen and Sporting Gentlemen) – illustrates the concept of “three generations to make a gentleman” using the self-made Abraham Lincoln and his aristocratic descendants as a case study in “The Lincoln Family: How American Aristocrats are Made” (The Protestant Establishment).

Chensvold touches upon the concept of education, writing that “a gentleman is never a specialist and always a generalist, and a four-year liberal education is preferable to a PhD in the mating habits of Amazonian beetles.” (Chensvold 2023, 112)

As a person working in academia, I found myself chuckling as I read this, and agreeing with the sentiment. I hold a firm belief in the value of a well-rounded liberal arts education and that led me to pursue an interdisciplinary doctorate in the humanities. Which brings me finally to the title of Chensvold’s book – The Philosophy of Style. This is the perfect title for the book.

This is a book about the world of ideas, and about the cultural underpinnings of style. All too often people conflate the term “style” as synonymous with “superficial.” Trends and trendiness are superficial; style and stylishness are not. In fact, the classics – whether we are taking about Plato and Aristotle, or the navy blazer and the regimental tie – are timeless. Chensvold reminds us that the classics are worthy of study, and his founding of Ivy-Style.com is a testament to that.

Pick up a copy of The Philosophy of Style. It is an excellent read, and it belongs in the pantheon of “Great Books” in the Ivy curriculum.