On October 1st something began bubbling in my subconscious. Ivy Style had reached its four-year anniversary, the MFIT exhibit had recently opened, and the accompanying book had been published.

I found that after four years of trying to look at this topic as objectively as possible, and talking to the men who were actually there during the heyday — Richard Press, Bruce Boyer, Charlie Davidson and Paul Winston — something unanswered remained.

I started thinking about Brooks Brothers and the college campus, which was chosen as the focal point of the MFIT exhibit, wondering about the connection between these two things. I soon found myself asking the most fundamental question: How do we explain how the Ivy League Look came about?

It’s easy to make generalizations, but hard to precisely articulate.

I next began thinking about the interplay between clothiers and their customers, focusing on the why as much as the what. Buttondown oxfords, plain-front trousers with cuffs, rep and knit ties — these are the whats, but what are the whys behind them? The answer couldn’t be simply “because that’s what Brooks Brothers sold,” when Brooks Brothers sold so much more that never became part of the Ivy League Look.

I telephoned Charlie Davidson and told him I was working on a piece though wasn’t sure where it was going. I started by asking him, “What portion of the Ivy League Look comes from Brooks Brothers, and what comes from the culture of young men on campus?” When Charlie, who’s been selling these clothes since 1948, responded, “That’s a good question,” I knew I was on to something.

The following essay is the result of my investigation. What began as an attempt to articulate Ivy’s origins grew into an overview about the whole broad arc of Ivy, how it codified and how it shattered into the complex “post-Ivy” era we’re in today.

In it I will argue:

• The Ivy League Look was as much about styling as the ingredients. And while the ingredients were relatively fixed and admitted new items slowly, the styling came from the campus and was always in a state of flux.

• It was the casual nature of the college environment and the importance of dressing down that led men in the 1930s to prefer rougher, casual fabrics — oxford cloth shirts, brushed Shetland sweaters, Harris Tweed jackets, flannel trousers — that has been the standard of good, understated taste for men on the East Coast ever since.

• The Ivy League Look included clothes for every occasion, from resort to formalwear, from city to country. However, the country element influenced the city far more than the other way around, and remains the most lasting influence of the genre.

• The Ivy League Look can be said to go through the stages of birth, maturity and decline, corresponding to specific points on a timeline.

• Once the look in its original, purist form ceased to be fashionable on campus, it ceased to be fashionable in society as a whole.

This lengthy piece will be presented throughout the week in five parts. New installments will be added at the bottom to preserve one cohesive post and comment thread.  — CC

• • •

The Rise And Fall Of The Ivy League Look
By Christian Chensvold

Part One: The Rise

In the late 1930s a new shoe became an instant hit on the Yale campus. First seen in Palm Beach in 1936, the “Weejun” penny loafer by GH Bass & Co. was immediately embraced by the students of New Haven. By 1940, the shoe store Barrie Limited was advertising its Horween penny loafers in the Yale Daily News, saying the shoe had “taken the university by storm.”

From the moment it appeared the penny loafer was an “instant classic” for wearers of the Ivy League Look, according to Charlie Davidson, 86-year-old proprietor of The Andover Shop in Harvard Square. Yet how do we explain the shoe’s overnight success, when so many shoes had come before and so many more would come later? For a genre of clothing that was slow to develop, that is characterized by its conservatism and supposed resistance to fads, this love-at-first-sight seems odd. Stranger still, the penny loafer was no temporary trend like the raccoon coat of the ’20s or the buckle-back chino of the mid-‘50s. Its place in the genre of clothing called the Ivy League Look remains to this day. It literally was an instant classic, embraced wholeheartedly and never relinquished.

Those Yalies who first donned the penny loafer in the late ’30s must have seen something special in the shoe, an inherent attractiveness and a harmony with the clothes they got next door at J. Press. “Casual slip-on shoes of the moccasin type are by far the most popular with students,” syndicated fashion columnist Bert Bacharach would later write in his 1955 book “Right Dress,” suggesting it was the penny loafer’s casualness of design — moccasin-style with no brogueing, laces, tassels, wings, nor anything else associated with a business shoe — that accounted for its instant appeal.

One thing’s for certain, however: No manufacturer could have anticipated or dictated the Weejun’s instant success. Something more mysterious and elusive was at work, the process of taste-driven natural selection by the closed culture of Eastern Establishment students of the 1930s. Young men and their peers, not clothing brands or magazine editors, decided what was fashionable.

Though it later achieved and lost mainstream popularity, the penny loafer remains available today at a wide range of prices, supported by both lifelong wearers and a steady supply of new converts. Typically paired with argyle socks in the 1930s, penny loafers were worn with white athletic socks in the ’50s and then sockless in the ’60s, the same item worn differently with each new decade.

The Ivy League Look is not simply a tailoring style accompanied by a specific group of furnishings and accessories. It consists of much more than just sack jackets, buttondown oxfords and penny loafers. It also consists of the taste-driven ethos that led some items to be accepted into the genre while others were rejected, and of a certain way of wearing the items that developed in the various upper-middle-class communities of the East Coast in the first half of the 20th century, chief among them the college campus.

“People made things a classic, not manufacturers,” says Davidson. “It’s people who made some things accepted and not others, otherwise how do we account for all the things that failed?”

Brooks Brothers And Ivy’s Big Bang

The Ivy League Look did not appear suddenly, but developed over time. “It was 30 or 40 years in the making without anyone knowing it would one day be called the Ivy League Look,” says Davidson. Although the clothing genre codified gradually, and while the lines that form the genre’s perimeters are debatable, there was something akin to an Ivy Big Bang, an instigating act that gave birth to this style of dress. And that is the introduction in 1895 of Brooks Brothers’ No. 1 Sack Suit.

Just as the jacket is the foundation of tailored clothing, this single item — natural shoulders, three button (after 1918, according to the Brooks Brothers book “Generations of Style,” by John William Cooke), dartless, with no waist suppression and paired with straight unpleated trousers — formed the blueprint for what would eventually become the Ivy League Look. And throughout the first half of the 20th century Brooks Brothers would continue to introduce a host of English items  — the buttondown oxford, Shetland sweater, polo coat, rep ties, argyle socks — that became staples of the Ivy genre.

But Brooks Brothers also offered countless other items — yachting and hunting regalia, double-breasted tapered suits, and other overtly English items less easily Americanized — that were never embraced into the Ivy League Look. Why? For the simple reason that they would have been out of place in a campus environment, the fertile ground where the style would codify and flourish, and where, as we’ll see, an air of casualness and nonchalance was paramount.

So while Brooks Brothers offered everything within the genre, it also offered much more. The Ivy League Look is narrower than the Brooks Brothers catalog (catalog here referring to what the company offered from roughly 1920-1970), and for this reason one could argue that Brooks Brothers’ smaller rival J. Press was a purer Ivy retailer, in that it offered a broader selection (such as in campus-oriented tweeds) within narrower perimeters. Brooks Brothers was Ivy and much more; J. Press was strictly Ivy.

England provided Brooks Brothers with many overcoats to sell to the gentlemen of America. But starting around 1910, one came to dominate the Ivy League Look above all others: the polo coat, another example of taste-driven natural selection at work.

According to Esquire’s Encyclopedia of Men’s Fashion, which draws heavily on historic articles from Apparel Arts and Men’s Wear, camel hair coats were noted for their dominance at the Yale-Princeton football game of 1929, having usurped the powerful but short-lived raccoon coat trend. Cooke writes, “This sporty camel hair garment… becomes the rage on college campuses during the Roaring Twenties.” Decades later, Bacharach would note, “Camel’s-hair polo coats are still the favorite type of outer wear among college men.”

The collegiate popularity of the raccoon coat in the 1920s, which fashion historian Deirdre Clemente has traced to Princeton, is a perfect example of a huge trend that was nevertheless selected for extinction, while the polo coat survived, indeed still available from retailers such as Brooks Brothers, J. Press, Ralph Lauren and O’Connell’s. The coat’s longevity is surely due to its sporting associations and easy ability to style informally — all things that would resonate with young men. It certainly looks more at home on the sidelines of a football field, as coach Vince Lombardi demonstrated throughout his career, and as dramatized in the movie “School Ties,” where polo coats are worn at a tailgate party for a prep school football game. Somehow a Chesterfield just wouldn’t look the same.

With the pink oxford, which rose to prominence in 1955 (the “year for pink” according to LIFE Magazine), Brooks Brothers once again introduced a new item into the Ivy genre. But it could never have anticipated the pairing a pink oxford with evening dress, as Chipp’s Paul Winston has recounted wearing, and which is, for lack of a better expression, a very Ivy thing to do (Charlie Davidson also recalls wearing a buttondown oxford with black tie, albeit a white one, which illustrates Chipp’s penchant for the “go-to-hell” look). Winston’s gesture serves as a perfect example of the styling side of things: Brooks provided the item, and the people found innovative ways of wearing it.

In summary, we can say that Brooks Brothers was the primary provider of the Ivy League Look’s raw ingredients, while the culture — meaning the world of young men competing and conforming sartorially in their WASPy East Coast environment — provided the styling. With each new decade Brooks Brothers showed what to wear, while young men, who drive fashion, showed how the items could be worn. As a wholly arbitrary fractional breakdown, we could say that 2/3 of the Ivy League Look was raw materials, which were relatively fixed and admitted new items slowly, while 1/3 was styling, which was in a constant state of flux.

Town And Country, Or Wall Street And Campus

As the Ivy League Look developed, references to Brooks Brothers increasingly focused on two specific realms: the college campus and the world of finance. In his essay on Brooks Brothers collected in the book “Elegance,” G. Bruce Boyer succinctly notes, “The Brooks Brothers suit seemed to peg a man somewhere between Wall Street and his country house, by way of the Ivy League.”

In a 1932 article, the New Yorker mentions the same two worlds: “Of course, Brooks still have their tables piled with the good old soft-roll, high-lapel sack coats that have been the accepted college and bond-salesman uniform for so long.” Presumably those bond salesmen, like Yalie Nick Carraway in “The Great Gatsby,” picked up the taste for Ivy while at school. “The novels of F. Scott Fitzgerald, for example,” writes Cooke, “are peopled with earnest heroes who hailed from the Midwest but who came to play in the racy world of New York via Princeton or Yale.”

This 1929 ad for Wallach Brothers also mentions the connection between the world of finance and the style-setting universities of Princeton and Yale:

As young men graduated from school to take their place in the world, including the financial industry, their clothing would change from country to town. Writing on Ivy League students in her 1939 book “Men Can Take It,” Elizabeth Hawes notes:

The conventional costume for all the right people is a pair of flannel or tweed trousers and a coat that does not match. When I asked them whether they were going to dress in their quite comfortable tweed for work when they left college, they responded firmly “no.” They were absolutely clear on that issue. They said they were training themselves — or being trained — to take their places in the world, and the required costume would be a neat business suit.

Although it was based in New York, Brooks Brothers specifically merchandised for the college man and sold to him via an army of traveling salesmen who frequented the prep schools and colleges of the Northeast. An 1898 Princeton football program includes an advertisement from Brooks Brothers, with copy reading, “Our stock for the present season continues, we believe, to show improvement, and will be found complete in all the little particulars that go to make the well-dressed man.”

This Brooks Brothers ad appeared in the University of Pennsylvania’s 1926 yearbook:

Brooks Brothers continuously revamped its youth-targeted line throughout the 20th century, adding its University Shop in 1957 and replacing that with Brooksgate in 1974. It’s current Flatiron shop is merely the latest incarnation of a century-long catering to young men as well as their fathers.

The Ivy League Look was for both town and country, Wall Street and campus, but, as we’ll learn, the campus element proved to be the more lasting influence of the two.

The New Guard

Although Charlie Davidson is the oldest-living, still-working purveyor of the genre, he doesn’t consider himself old guard. The Ivy League Look was in full bloom in the 1930s, he notes, well before his founding of The Andover Shop in 1948. At the time Davidson considered himself to be offering clothing within an already established genre, yet targeted at the local geography. This sentiment is echoed by Richard Press, who says that J. Press’ locations outside of New York were meant to provide Brooks Brothers items in areas with an Ivy League campus (Cambridge, Princeton), but no Brooks; only Columbia had that.

As George Frazier put it in 1960, “Around the turn of the century, Arthur Rosenberg, then the foremost tailor in New Haven, began to exploit this [Brooks Brothers] style among Yale undergraduates, and, not long afterwards, J. Press, also of New Haven, fell into line.”

These smaller retailers outside New York took the Brooks Brothers template and focused more on the country side of the genre rather than town. And yet all these other players who used the ingredients that Brooks Brothers had provided felt that taste and small differences distinguished them. “We all thought our taste was better than our competitors,” says Davidson. “Norman Hilton, for example, had exquisite taste, and when you get to the commercialization of the Ivy League Look, he’s at the forefront.”

The most important and lasting clothier providing Brooks-based style for college towns was J. Press. Press’ difference from Brooks is summed up by Episcopal Archbishop of New York Paul Moore, Jr., who writes that Jacobi Press’ “tweeds were a little softer and flashier than Brooks Brothers tweed, his ties a little brighter.”

Richard Press, former J. Press president and grandson of the founder, has also stressed Press’ emphasis on country rather than town. “I think that one of the major differences between Brooks Brothers and J. Press,” he states in his 2011 Q&A with Ivy-Style.com, “beyond the obvious size, was that we were known as a campus store, whereas Brooks Brothers was much more urban.” Indeed, the merchandise for J. Press’ New York store was less purist than its campus shops. “If you look at our brochures,” says Press, “you’ll see that the two-button darted suit was sold only in the New York store, and it probably represented 40 percent of our suit sales there.”

While Brooks Brothers, originator of the Ivy League Look’s ingredients, was based in New York, New Haven is the top candidate for Ivy’s spiritual home. In a 2004 article entitled “The Yale Man,” the New York Times writes, “‘Natural shoulder’ was what men’s magazines called the Yale look, and for decades the clothing stores near campus at Elm and York Streets in New Haven were the natural-shoulder capital of the universe.”

Style setting also thrived in New Haven. “Students and their professors enunciated a new style,” says Press, “with their dirty white bucks, horn rimmed glasses, Owl Shop pipes, raccoon coats, J. Press snap brim hats, stuff that was too informal and sporty for Brooks. Big difference between city and campus wear and Brooks pushed the former, the rest the latter.”

Finally there was the issue of price: “Perhaps most important issue for the proliferation of Ivy,” says Press, “Brooks was too expensive. J. Press and competitors adapted to the more restricted allowances of the campus population and worked below Brooks price points.”

Although these new-guard clothiers used the template created by Brooks Brothers, they did so in the cultural environment where the Ivy League Look’s styling was at its most fertile: the campus. And because these clothiers and the student body were part of the same community, they had a close, symbiotic relationship. Students needed the clothiers to get what they wanted (and to want things they’d never seen before), and clothiers needed to find out what was popular. As a result, Ivy clothiers never left their eye off college men. In 1962, Sports Illustrated notes, “Representatives of the New Haven tailoring establishments—J. Press, Fenn-Feinstein, Chipp, Arthur Rosenberg, et al.—entrain for Cambridge to render biennial obeisance and to see what the young gentlemen are wearing.”

Earlier, in a 1938 article entitled “Princeton Boys Dress In Uniform,” LIFE Magazine writes, “The fact of the matter is that tailors and haberdashers watch Princeton students closely [and] admit they are style leaders.”

Clothiers also made sure college men knew they cared deeply about student tastes. This ad by Irv Lewis, a clothier serving Cornell, explicitly elucidates the relationship:

“The key element of successful campus shops,” Richard Press summarizes, “was their ability to establish personal relationships with students, faculty, coaches and administration. Brooks Brothers in New York and Boston was too diffused, and while each top customer had his clothing man, it changed from floor to floor, from furnishings to shoe department.”

College Students, “The Best-Dressed Men To Be Found Anywhere”

Bert Bachrach states that before World War II many clothing experts considered college students “the best-dressed men to be found anywhere.” The following passage, from a 1933 Apparel Arts article entitled “Clothes For College,” is a prewar reference to this very thing:

Today the college man is looked upon as a leader of fashion, a man who dresses inconspicuously and correctly for all occasions, thanks to the leadership of smart Eastern Universities, which have a metropolitan feeling, or at least are near enough to metropolitan areas for the students to feel all the influences of sophisticated living. We can thank the present-day “collegiate” element for the return to popularity of the tail coat, for the white buckskin shoes, for the gray flannel slacks with odd jackets, and for various other smart fashions which are typical of university men today.

For on-campus wear there is a general acceptance of country clothes in the typical British manner, such as odd slacks and tweed jackets, country brogues and felt hats. This is the way the undergraduates at smart Universities and prep schools dress today during classes.

Another Apparel Arts article from the same year shows that the Eastern Establishment virtues of being dressed down from a formal perspective and dressed up from a casual one most likely have their origin in the collegiate approach to dress that reached fruition in the ’30s. The article includes the quote “a perfect example of the studied negligence that is taken as the standard of good taste among college men,” and goes on to say:

The American University man is justly famed for representing, as a class, a high standard of excellence in personal appearance. Much of the secret of this distinction lies in the fact that the first thing the freshman learns is the importance of never looking “dressed up,” while always looking well dressed. Recently the tendency toward an effect of “careful carelessness” has been emphasized through the trend toward rough, almost shaggy, fabrics for town and campus wear.

The Ivy League Look’s emphasis on rough, hearty fabrics comes from students’ penchant for rustic, country clothes over more starched and pressed town clothes:

There’s a trend toward rougher suitings on all the eastern campuses. Early last fall fashion observers reported the growing popularity, particularly at Princeton and Yale, of rough tweedy type fabrics for all general knock-about campus wear — in fact for all except strictly town purposes. Worn smartly with either flannel, gabardine or other type of slacks, these rough fabrics of the Shetland or Harris variety showed a considerably increased acceptance on the part of the fashion leaders during the Palm Beach season.

Writing in the Saturday Evening Post in the 1930s, Arthur van Vlissingen states that trends aren’t dictated by manufacturers, who couldn’t afford to gamble on a fad that may fail, and that men only embraced a new item once they saw other men wearing it. These style setters were often found “at the places where the country’s leisured and socially prominent loaf, such places as Palm Beach and Newport” (coincidentally Brooks Brothers’ first two locations outside New York), and the college campus. “The fashions in clothing worn by our male population, between the ages of 14 and perhaps 25,” he writes, “usually get their start at Princeton.”

Vlissingen proceeds with the following sartorial breakdown of the Ivy League’s Big Three:

Harvard is a very large university, in a great city which influences the students’ styles heavily. [But] it holds to a tradition of careless dress—well-made clothes seldom dry-cleaned and never pressed. Yale is more compact and more finicky, but New Haven is also a large city. Princeton is in a smaller town, off by itself where it 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.

As these passages illustrate, if college men of the 1930s — the fortunate few able to afford school in the midst of the Great Depression — were among the nation’s best dressed, they achieved this status despite an insistence on never looking too dressed up by the standards of their time. Elements of the Ivy League Look, such as the penny loafer and polo coat, were embraced into the genre because compared to other footwear and outerwear options they were relatively casual. This certainly holds true for the buttondown shirt, which Bachrach calls the shirt of choice for college men because “the construction of the shirt, which allows the collar to roll rather than lie flat, provides the casual touch which young men like.”

In regards to tailored clothing, Bachrach suggests that the prized Ivy color of charcoal was embraced for its ability to take a beating without looking dirty:

The most important style set by the colleges in recent years has been suits and slacks in charcoal, a gray so dark in tone that it approaches black. This color has become almost a uniform at Harvard, Yale and Princeton. It is practical for a suit since it rarely shows dirt or signs of wear.

If men at Ivy’s Big Three were style setters for the whole nation, that can hardly be said of Columbia, the most interesting sartorial case among the Ancient Eight. 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.

This passage from Tobias Wolff’s novel “Old School,” set at a prep school in 1960, serves as a dramatization of how Columbia was viewed compared to the other Ivies:

I wanted out. That was partly why I’d chosen Columbia. I liked how the city seethed up against the school, mocking its theoretical seclusion with hustle and noise, the din of people going and getting and making. Things that mattered at Princeton or Yale couldn’t possibly withstand this battering of raw, unironic life. You didn’t go to eating clubs at Columbia, you went to jazz clubs. You had a girlfriend — no, a lover — with psychiatric problems, and friends with foreign accents. You read newspapers on the subway and looked at tourists with a cool, anthropological gaze. You said cross town express. You said the Village. You ate weird food. No other boy in my class would be going there.

In contrast, “Princeton was especially isolated and characterized by a particularly fervent and insular culture,” writes Patricia Mears in “Ivy Style: Radical Conformists.” Princeton also had the most affluent student body, with 80 percent coming from private schools during the inter-war years. “Although it lay part way between New York City and Philadelphia, Princeton was more geographically isolated than its rivals Harvard and Yale. Its campus was situated in a rural environment, surrounded by acres of bucolic farmland. As such, Princeton relied more intensely on its internally crafted society. The blend of wealth, manners, and aristocratic social construct proved to be the breeding ground for the creation of the elegant Ivy style.”

The Way You Wear Your Hat

The popular term employed during its heyday, the Ivy League Look, is interesting for its inclusion of the word “look.” While there are references to “an Ivy League suit” from the period, the popular term was “look,” not “tailoring” or “clothes.” This broader term suggests that there is more than just clothing involved, but also a proper haircut, and if not a particular social context, then at least all-American good looks. In the 1964 film “Ride The Wild Surf,” Barbara Eden’s character refers to her love interest as “Mr. Ivy League” for his handsomeness, poise and “scrubbed” appearance as much as his conservative clothing.

“Look” is also broad enough to encapsulate how the items are worn, since that is as much a part of dressing in a certain style as the components themselves. This illustration from a 1926 Vanity Fair article on collegiate dress includes a caption stating that Harvard men had their own way of pushing their hats “into a shape never conceived by hat manufacturers”:

Hawes includes several passages attesting to Harvard men’s predilection for an affected Old Money look:

At Harvard they have something called “white-shoe boys.” I gather it is okay to be one if you feel that way. It appears to be the Harvard idea carried to its furthest extreme. These are the sloppiest and worst-dressed of all the Harvard men, I was told. They wear dirty black and white shoes which turn up at the toes, black or white socks and gray flannels, very unpressed, tweed coats — and collars and ties, of course… The thing that distinguishes a “white-shoe boy” is his shoes — and the fact he has the guts to wear them and still feel okay socially.

In 1869 Harvard challenged Oxford to the first of its boat races, and it’s possible that the English influence on Harvard goes back to these sporting competitions. Hawes continues:

The coat should have leather pads on the elbows. These are often put right onto new coats. This is because the country gentlemen of old England have a habit of preserving their tweed coats for generations, mending them from time to time with leather pads and what not. The Harvard boys, not to be outdone by old English exponents of the finer things in life, are going them one better.

After noting that Yale students are much better dressed, Hawes adds, “I think the superiority complex of Harvard probably led them originally into the oldest clothes as a form of snobbishness.” Nevertheless, “I might add that the [men’s wear] trade does not consider Harvard as any source of style ideas at all.”

Russell Lynes’ 1953 Esquire article on the “shoe hierarchy” at Yale further emphasizes how much of the Ivy League Look came down to the elusive qualities of attitude:

… the social smoothies — butterflies in button-down collars — short haired, unbespectacled and with unextinguishable but slightly bored smiles. They wear the current college uniform, Ivy League version, but they wear it with an air of studied casualness, as though they would be at home and socially acceptable anywhere in whatever they had on. The uniform, of course, is the familiar khaki pants, white bucks, or possibly dirty white sneakers, a slightly frayed blue or white button-down Oxford shirt, no necktie, and a grey sweater which the wearer expects you to assume was knitted for him by a girl. On occasions that demand a gesture of formality, dark grey flannels without pleats supplant the khaki pants, a necktie (either regimental stripes or club tie) is worn, and so is a tweed jacket with vent, pocket flaps, ticket pocket, and three buttons. For bucks substitute well-shined cordovan in season. For city wear the uniform is a dark grey flannel suit; the haberdashery stays much the same.

Charlie Davidson also stresses what he calls the “attitude” long associated with wearers of the Ivy League Look, which he describes as a nonchalant approach to dress combined with poise and an air of self-assurance. Whether this poise is real or feigned is up for debate. “The Ivy League Look was a way of life more than anyone has been able to put a finger on,” he says. “In the beginning it was a very closed kind of thing, and so much of it was the attitude of not caring too much and being very assured of their station — and of having the right clothes.”

From the codifying period of the ’30s to the heyday of the ’50s and ’60s, the styling component of the Ivy League Look was constantly changing with each new group of classmen. For a young man to be considered well dressed by his peers in the ’30s or cool in the ’50s, it wasn’t enough just to choose the right items. They also had to be worn in the way that was then fashionable. And what was fashionable was always shifting, and emanated from campus culture.

For example, on page 59 of the 1965 book “Take Ivy,” a student strolls the Princeton campus wearing olive-colored shorts, penny loafers with no socks, and a buttondown oxford with the sleeves down, all topped by the neat haircut that epitomizes the era. He has used the ingredients the genre but put them together in a way that expresses both his personal whims as well as the style of his era, and nothing in the image suggests that a retailer, manufacturer or fashion editor told him to put together his outfit this way.

For a cinematic dramatization, the 1956 film “Tea And Sympathy” shows students styled uniformly in a combination of buckle-back khakis, white canvas sneakers, blue oxford shirts and gray crewneck sweatshirts. For that group of students in that particular location at that particular time, the juxtaposition of a dress shirt with a piece of athletic wear was evidently a style imperative.

This leads us to yet one more inexplicable preference in the Ivy clothing genre worth mentioning: The crewneck sweater. While V-necks and cardigans were always offered by Ivy clothiers, somehow the crewneck became the standard cut, even when worn with a necktie, as the Yale student below demonstrates:

It was something the youngsters picked up early; this outfit is also notable for how the components are put together as much as the items themselves:

It should come as no surprise that the preference for the crewneck can also be traced to style setting at Princeton, where a freshman orientation guide, for reasons unexplained, admonished the younglings not to wear V-neck sweaters. Much later, in his 1983 book “Class,” Paul Fussell would wryly explain why the crewneck is upper middle and the V-neck merely middle.

The Ivy League Look should not be thought of as merely a collection of ingredients. Equally important are the cultural forces that led certain ingredients to be embraced into the genre over others, even though this importance is difficult to trace, clouded as it is in the mists of fashion. Then there’s the element of how the items were worn, an equally vital element of the Ivy League Look. All the elements are a reflection of the tastes and cultural values of the Eastern Establishment, and the tastes and values, specifically, of college men during the interwar years.

The Legacy Of The Heyday

The 1959 movie “The Young Philadelphians” provides a helpful dramatic illustration of one character’s transition from country to town, or from campus to law firm, while still dressing within the confines of the Ivy League Look.

In campus scenes the protagonist, played by Paul Newman, wears a boxy corduroy sack jacket, slim flood-length khakis, white socks and penny loafers. Once he becomes a practicing lawyer, he dons a conservative gray suit, rep tie, pinned-collar shirt and lace-up shoes. While both jackets are undarted and natural shoulder, and all his clothes could have come from the same place, stylistically — in the simplest terms — he’s gone from the campus side of the genre to the Brooks Brothers side, or more from the styling-driven side to the product-driven side, or from an emphasis on how to wear the items correctly to how to select them correctly.

The book “Generations Of Style” includes a Brooks Brothers timeline, and while the listing for 1961 is oversimplified, it nevertheless makes the point that the campus-oriented side of the genre is the more lasting and influential: “A new style of casual, conservative dress defines the country: khakis, Shetland crewnecks, and button-down shirts set the tone… Campus style predominates, with the corporate ‘Man in the Gray Flannel Suit’ now being replaced by the more casual dress: penny loafers, Argyle socks, and tartan plaid sportcoats and shirts.”

Today, when a man passes you today on Madison Avenue and you notice how “Ivy/preppy/trad/whatever” he looks, he’s probably wearing loafers, flannels, a three-button sportcoat, buttondown oxford, and conservative necktie. You’re far more likely to see a man dressed this way than in the far more anachronistic business ensemble of worsted gray sack suit, white pinned club collar and longwings, and if you did, you’d be more likely to say “how IBM” or “how ‘Mad Men'” than “how Ivy League.”

The association of the Ivy League Look with the campus is so strong that even in the downfall year of 1967 an arch-sybarite like Hugh Hefner would remind his biographer of a dapper undergrad:

Black-haired, intense, slightly under six feet, he looks, in his often-photographed costume of white button-down shirt, orange cardigan sweater, slacks, loafers and pipe, like a college senior on his way to class.

Men who wear this genre of clothing today — by whatever name they call it — owe an equal debt to the illustrious firm of Brooks Brothers for introducing so many of the raw elements, and to the countless anonymous college men from the first half of the 20th century who codified the components of the Ivy League Look for future generations.

Part Two: The Fall

From Young Men’s Clothes To Old Men’s

In “Decline of the West,” Oswald Spengler argues that all cultural expressions go through the organic stages of birth, maturity and decadence. The Ivy League Look is certainly an expression of culture, and for it I’d suggest a birth of 1895, a golden age in the 1930s when the style was limited and aristocratic, a democratic silver age during the ‘50s and ‘60s when it was popular, and an end to the silver age in 1967, followed by a gradual decline into our present postmodern era.

This decline was expressed in a variety of ways, and the legacy of the genre is characterized by a range of conflicting manifestations, from the irrelevance of contemporary J. Press and the sack suit, to the generic “timelessness” of blazers, khakis, buttondowns and striped ties available from retailers as mundane as Lands’ End, and to fashion industry pastiche exemplified by some of the more outré items by Thom Browne, Ralph Lauren Rugby, and various neo-prep brands.

If the Ivy League Look didn’t die, then certainly a kind of descent into decadence occurred, which is attested by the mere fact that Brooks Brothers, instigators of Ivy’s big bang with its No. 1 Sack Suit, no longer offers the very item that gave birth to the entire genre, but instead sells a fashion novelty version called the Cambridge.

Furthermore, Brooks Brothers and J. Press long ago changed owners and merchandising strategies and can no longer be counted on to reliably provide what were once genre-distinguishing traits such as natural shoulder and collar roll.

But the death of Ivy can’t be blamed entirely on manufacturers, who simply cater to the needs of the culture as expressed in the marketplace. The Ivy League Look was once a vibrant, dynamic style that was an expression of the values of the Eastern Establishment. Later it was good, smart, current taste for a larger portion of the population. If Ivy is no longer available today in its original form, it is because fashion, which reflects society, has changed. The inversion of values that took place during the cultural revolution of the late ’60s, a topic that has been explored exhaustively by cultural historians and which is too big to discuss here, created a new cultural engine that drove fashion from the bottom up rather than top down.

While in the ’50s and early ’60s many actors and pop singers wore the Ivy League Look as a smart and current style, this was no longer the case after the upheaval of the late ’60s. When pop singers did take up a version of the look, as Dexys Midnight Runners did in 1985, it was the preppier version of the look then current. It was also the temporary costume of entertainers who had radically different looks before and after. In the 1950s and ’60s, pop icons could wear white bucks, buttondowns, neckties and soft-shouldered jackets and come across as sharp and with it. But with contemporary music groups such as Vampire Weekend, or in the films of Wes Anderson, Ivy staples come across as irony.

A glance through “Take 8 Ivy,” the sequel to “Take Ivy,” shows Ivy League students of the 1970s wearing the same plebeian sneakers, jeans and t-shirts worn by every other young person in America.

In assigning an arbitrary date for the end of Ivy, I suggest the year 1967. The change that occurred that year — the year of the infamous “Summer of Love” — is summed up tersely and dramatically in the following passage from “The Final Club” by Geoffrey Wolff (Princeton, ’59). The year 1967 witnessed a sartorial dismantling that was complete by 1968, when a new era was in full flower-child bloom:

Lining the second-floor hall were group portraits of Ivy members, and Nathaniel paused to examine them. Till 1967 the club sections were photographed indoors, in the billiard room; dress was uniform — dark suits, white shirts, Ivy ties. In 1967 a white suit was added here, an open collar there. In 1968 the insolent, smirking group moved outside, and was tricked out in zippered paramilitary kit, paratroop boots, tie-dye shirts, shoulder-length locks, and not a necktie in view.

Although the broader culture was changing rapidly and the hippie movement was spreading, the new open admissions standards at elite universities were changing the student body. Style-setting schools such as Princeton and Yale were no longer populated predominantly by kids who had gone to prep school, where they were forced to wear a jacket and tie every day and maintain a neat haircut. Schools were also dropping their jacket-and-tie dining hall dress codes. It’s impossible to underestimate the pace of social change in the late ’60s; the Ivy League Look, in its original guise, was slated for extinction, and the name attached to it during its popular silver age would fall into almost immediate archaism.

But what’s most important here is that once the Ivy League Look ceased to be fashionable on campus, it ceased to be fashionable period. More specifically, one could argue that once guys at Princeton stopped wearing it, it was over. The campus had always been the stronghold of the look, the place where it flourished for six decades, and was necessary for the look’s broader cultural relevance. Smart young men from the middle class and above had wanted to dress this way for 50 years. Originally it was a small number; later it was larger. Now suddenly no young people wanted to dress this way.

Other symbolically interesting things also occurred in 1967. Brooks Brothers’ president left the company after serving 21 years, all throughout the Ivy heyday, and Ralph Lauren goes into business. These two events are like two sides of the same coin. The man who helmed Brooks Brothers throughout its glorious postwar heyday retires, while Ralph Lauren launches his career. It’s an eerie foreshadowing of the role reversal that would happen over the ensuing decades, during which so much of Lauren’s merchandise would be closer in spirit, style and quality to classic Brooks Brothers than Brooks Brothers’ contemporary merchandise.

Within a few years of 1967 the UPI was calling the look dead, as in this story from 1971:

The Ivy League look as it used to be called died in the recent fashion revolution and the slope-shouldered, three-button jacket is almost a thing of the past. The suits and sports jackets being worn are strictly for special occasions.

Once it was no longer fashionable, the Ivy League Look, to return to the big bang metaphor, experienced a kind of supernova that shattered it into parts, which varied depending on wearer and context.

J. Press and Brooks Brothers continued, yet their clientele would gradually grow older as the look ossified from being young and current to being old and stodgy. J. Press stayed truer to the look, but as society changed rapidly around it, J. Press experienced a complete inversion in its relation to the broader culture, becoming what most would consider a provider of old men’s clothes, when from its founding in 1902 until 1967 it catered largely to young men.

The Twilight Of Ivy And Dawn Of Preppy

Some young people did continue to shop at the same clothiers and wear much of the genre’s items, but fashion was changing rapidly and the new version of youthful, Eastern Establishment style came to be known as preppy. The new generation had a much more casual approach to dress, reflecting changes in society as a whole. This passage from Alison Lurie’s “The Language Of Clothes” from 1979 shows how many of the Ivy League Look’s sportier items were being worn with a new attitude:

What distinguished the Preppie Look from the country-club styles of the 1950s was the range of its wearers. These casual garments were now being worn not only by adolescents in boarding schools and Ivy League colleges, but by people in their thirties and forties, many of whom would have considered such styles dreary rather than chic a few years earlier. Moreover, the Preppie Look was now visible in places and on occasions that in the 1950s would have demanded more formal clothing. Preppies of both sexes in madras check shirts and chino pants and Shetland sweaters could be seen eating lunch in elegant restaurants, in the offices of large corporations and at evening parties-as well as in class and on the tennis courts.

During the preppy ’70s, just as it had been previously, styling and the items themselves were equally important. Lurie notes that the preppy look was distinguished as much by its items as by their combinations, which included novel layering tricks such as jersey turtlenecks or polo shirts worn under oxford buttondowns, accented by a sweater draped around the neck.

As WASPs were gradually losing their stranglehold on power and influence, becoming shameful reminders of the old boys’ club elitism, their taste and lifestyle was beginning to be fetishized and marketed. In 1980 Lisa Birnbach released her detailed look into the culture of the preppy Northeastern upper-middle class, “The Official Preppy Handbook,” and the book so fascinated the nation it became a best-seller. At the same time the rise continued for Ralph Lauren, the doppelganger figure who can be seen as both saving the Ivy League Look from extinction by keeping alive the taste for it, albeit repackaged as fashion, and as commodifying totems of what were once expressions of culture. In “Taste: The Secret Meaning Of Things,” Stephen Bayley suggests that some kind of cultural line had been crossed following the fall of the Ivy League Look and the advent of postmodern, post-Ivy consumerism:

Ralph Lauren was after what Brooks Brothers once had, but packaged it more effectively so as to anticipate, appeal to and satisfy hitherto unrecognized longings among consumers. Interestingly, his critics (easily outnumbered by his happy customers) invoke arguments against him which echo the sumptuary laws of Renaissance Florence and England: “How does a working-class Jew from Mosholu Parkway dare pass off the tribal costumes of the Ivy League as if he owned them?”

Each fall season Ralph Lauren continues to pay tribute to the Ivy heyday with a few retro replicas. These typically tweed sportcoats come with such distinguishing Ivy details as natural shoulders, 3/2 rolls, patch pockets, swelled edges and lapped seams. However, they differ considerably from the kind of quotidian mufti once available at the Yale Co-op in that they have darted chests and carry a $1,300 price tag.

The other fragments that resulted from Ivy’s supernova are the category of vintage clothing anachronism, in which guys with hip sensibilities seek out heyday specimens prized for their authenticity, and the postmodern parody category, in which fashion designers (not haberdashers or merchandisers, the previous creators of the products) take the classic grey sack suit and turn it into a cartoonish gimmick, as in the case of Thom Browne.

Ivy-Style.com’s readership reflects this broad range of motivations for wearing the style, from the J. Press-clad fuddy duddy to the updated traditionalist in Ralph Lauren tweeds and flannels, and from the prep-with-a-twist fashion guy in Gant to the midcentury retro-eccentric dressed head to toe in vintage. It’s a perfectly postmodern incohesive mishmash of taste, temperament and social background all able to find in this genre of clothing something that resonates.

A Rose By Any Other Name

As the Ivy League Look fell into its death throes of cultural relevance, its name became immediately old fashioned. Originally it doesn’t seem to have had a name. “Natural shoulder” seems to have been the closest actually used by clothiers and their customers. The assiduous reporting by the media in the 1930s of what guys at Princeton were wearing is noteworthy for the detailed descriptions of the clothing combined with the complete lack of any attempt to give the style a name. “University fashions” was a typical headline for Apparel Arts, or “campus wear.”

The term “Ivy League Look” came into popularity in the ’50s, perhaps entering the popular lexicon as the result of LIFE Magazine’s 1954 story “The Ivy Look Heads Across US.” After 1967, once the clothes ceased to be fashionable, the term certainly became archaic. Fortunately a new word — for the broader culture — arrived at at just the right time to describe the latest version of the youthful Northeastern upper-middle-class look. “Preppy,” which entered the popular vocabulary in 1970 via the hit film “Love Story,” had a fresh ring to it.

Since its fashion moment in the ’80s, the term “preppy” has become gradually watered down to the point of meaninglessness, with almost no connection to the style and values of the people it described in 1970. Yet despite the efforts of the MFIT’s “Ivy Style” book and exhibit, not to mention Ivy-Style.com, preppy remains closer to the tongue, however bitter it tastes, than “Ivy League” when describing this genre of clothing. If you see someone walking down the street dressed head to toe in J. Press, says Charlie Davidson, “you wouldn’t even say he looks very Ivy, you’d say he looks very preppy, or something like that.”

The struggle for just what to call the post-Ivy remnants of the genre in a way that doesn’t sound girly, as preppy does today, or archaic and elitist, as does the Ivy League Look, accounts for the adoption in certain quarters of the term “trad.” On the surface trad sounds like a snappy and contemporary replacement, but with no historical tradition behind the term, trad quickly became a futile exercise on Internet message boards with endless debates about what qualified as trad and what didn’t, and with each opinion more subjective than the last.

It’s worth noting that in Japan and England, where the clothes were not an expression of their own dynamic and changing cultures, the clothes continued to be called “Ivy,” and much of the styling remained frozen in its heyday form.

With the Ivy League Look reaching full fruition in the 1930s and ending as a current and relevant fashion in 1967, its full flowering spans just three decades. Indeed, there are more years that have passed since the end of the heyday than the years from codification to heyday’s end.

The golden age was the 1930s, when the look was only available from a small number of clothiers and worn by a relatively small number of men. By 1957, in the middle of the silver age of widespread popularity, the look was already considered to be in decline by the old guard. In the April 7, 1957 edition of Town Topics, Princeton’s community newspaper, Princeton-based clothiers lamented a slide in formality among the student body. “You’ve got more of a cross section now,” concluded Joseph Cox of Douglas MacDaid, “not so many rich kids.”

The mass popularity of Ivy during heyday, with all of the department store knock-offs that Richard Press likes to dismiss as “Main Street Ivy,” actually holds within it the seeds of the look’s demise. For fashion is fickle, and Ivy fell from mainstream popularity into irrelevance practically overnight. While it’s true that the establishment was abandoning the look, at least among the younger members, it’s also the case that the middle class no longer had the desire to ape the establishment, at least not overtly. Brooks Brothers and J. Press stuck to their guns as much as possible and for as long as possible, watching their clientele slowly ossify, and Main Street clothiers quickly changed with the winds of fashion.

However, the silver age also cemented Ivy’s legacy in the “classic” and “timeless” sense. It continues — by whatever name and in iterations that conform with contemporary style — to be worn by anyone with the taste for it. And good taste should be available to anyone with the sensibility to appreciate it.
 Natural-shouldered tweed jackets, grey flannel trousers, oxford-cloth buttondowns, rep and knit ties, argyle socks, tassel and penny loafers, polo coats, Shetland sweaters, side-parted haircuts and horn-rimmed glasses still carry all the baggage, good and bad, that this Northeastern, upper-middle-class, “Ivy/preppy/trad/whatever” look will always have.

The farther you go into postmodern parody, of course, the less baggage the look carries, because in this case it’s just fashion, which is another way of saying it doesn’t mean much. But the straight-up wearer of the Ivy League Look, who projects his natural shoulder and rolled collar with utmost earnestness, gets all the prestige and all the squareness that comes from being dressed traditional.