What was the Ivy League Look? The past tense is necessary, because the phrase is almost certain to draw a blank. There’s no longer any distinctive mode of dress associated with America’s most famous colleges. Students there dress much like students everywhere in the world: a utilitarian combination of sneakers, denim, and hooded sweatshirts. “Preppy” is more likely to activate some visual and cultural associations. The term was brought to national attention by the 1970 novel and film Love Story, and came to denote a patrician combination of tweed, flannel, and warmly burnished leather. The hero, Oliver Barrett IV, defies his family to marry the working class woman he loves. Against the rapidly degenerating standards of the period, though, the film’s Oliver (played by Ryan O’Neal) looked like an old man, thickly bundled up for a winter of discontent rather than disrobed for a summer of love.

A few decades later, the term became both more commonplace and more polarizing. For buyers of how-to guides such as The Official Preppy Handbook, it was an invitation to a form of consumer activity that was simultaneously conservative and aspirational. Even more garish versions of what Oliver Barrett might have worn on winter break in Palm Beach were now available at every mall in America. For the audiences of the period’s exultant teen comedies, on the other hand, the preppy—or the diminutive “prep”—had become a stock villain. Rather than defying the expectations of his elders, he sought to impose them on everyone else. The fame of James Spader and other actors who specialized in portraying this character has long since receded. But the clothes they wore have never shaken that unpleasant reputation.

It’s a curious career for a look that began, essentially, as a gimmick. In 1902, Jacobi Press, a Jewish immigrant from Latvia, opened a tailoring and haberdashery business in New Haven. He was eager to differentiate himself from many rivals for the Yale student trade and specialized in clothes that were a touch softer and brighter than his competitors’ wares. This is how the Ivy League Look was born, although it didn’t coalesce aesthetically until the 1930s or break out of the college and boarding school market until the 1950s.

More than half a century after its heyday, the Ivy Look has become a historical curiosity. And it has fallen to Jacobi Press’s grandson Richard to recount its rise and fall. Although he has no managerial role in the company, which was sold to a Japanese conglomerate in 1986, Press has re-emerged as an in-house elder statesman, historian, and brand ambassador. The two volumes of Threading the Needle combine Press’s recollections of family and his own career in the shmatte business, shopping advice, and social commentary (often elegiac in character). Of course, since the books are by a salesman descended from generations of salesmen, they’re also advertising.

The interest of Threading the Needle lies partly in its careful and appropriately unsystematic dissection of the Ivy League aesthetic. For different reasons, the American handbook writers and the Japanese customers who embraced the Look after it passed out of fashion in its native habitat both treat it as a formula. It’s simple: combine, say, a navy blazer, a “rep” striped tie, and flat-front chinos—and the Look is complete. This is a touch anachronistic, actually, because a certain eclecticism had previously been a distinguishing feature of Ivy style. The principle of this manner of dressing, reduced to a slogan, could be expressed as “layered separates.” In other words, the ideal outfit is composed of pieces that do not match in material, color, pattern, or texture yet magically create a coherent effect. Ralph Lauren, a one-time Brooks Brothers salesman and eventually tycoon of prep, would develop this skill to virtuosic and sometimes ludicrous heights.

The eclectic quality of Ivy League dressing extends to its cultural and geographic sources. The basic elements were largely imported from England, reflecting the dominance of men’s fashion first established by Beau Brummell. But the pioneers of Ivy also took inspiration from Norway (loafers), the remote North Atlantic (fishermen’s rough sweaters), and India (madras). Part of the Look’s original appeal was that it was slightly cosmopolitan at a time when international travel was more difficult and expensive than it is today.

Finally, the Look combined formal and casual elements in ways that are hard to recognize today, when neckties are disappearing even at weddings and funerals. At the outset, though, Ivy League essentials including patterned tweeds, button-down collars, and soft flannel trousers were all considered sportswear, literally unsuited for town and business settings. There was something a bit rebellious about the way Yale and Princeton men continued to wear these things in their post-graduate lives. (Despite its role in Love Story, Harvard was not considered a stylish campus). This subtle insouciance helped distinguish Ivy style as purveyed by J. Press from comparable offerings at Brooks, which had a more urbane and professional quality.

The result was a cousin of what the menswear writer Bruce Boyer calls the “English country house look,” still recognizable in The Crown and other period dramas. But it was more youthful, sportier, and lacked the whiff of generational decay. In short, the Ivy League Look was American. Along with cowboy outfits and the protective gear once favored by aviators and motorcyclists, it remains among our few original contributions to the menswear canon. You’d still be stylishly dressed today by combining the definitive piece from each genre: a pair of blue jeans, an Oxford cloth shirt with a button-down collar, and a simple leather jacket or pair of sunglasses.

Press’s loving accounts of the invention, production, and marketing of the Ivy inventory will delight the sartorially inclined, some of whom may find themselves compulsively browsing the J. Press website as a result. More casual readers may prefer the cultural history that his reminiscences document. As the origin story of J. Press indicates, the Ivy League Look was a coincidence between the business interests of immigrant, largely Jewish entrepreneurs and the social prerogatives of their upper class customers. Relations between these groups were not so happy as their aesthetic connection. Although he’s proud of his grandfather’s and father’s brushes with luminaries of the Protestant establishment, Press also notes the subtle and not-so-subtle condescension and anti-Semitism they faced. Clothiers, after all, are tradesmen. And tradesmen are not gentlemen, no matter how tasteful the goods they supply.

The story of the Ivy League Look is also a story of technological change. Before World War II, a good suit was cut to measure and constructed largely by hand. By the mid-century, however, mass production had become the norm for all but the most demanding customers.

On the one hand, standardized inventory was good for business. Once a single tailoring shop, J. Press became a minor chain, with stores in New Haven, New York, Cambridge, Princeton, and San Francisco. This expansion paralleled a national fad driven by the growth of higher education, the corresponding shift to white collar employment, and the 
ubiquity of television, which tended to standardize consumer tastes across classes and regions. Not everyone could afford J. Press or lived near its retail outlets or road shows. But for a while you could buy reasonable approximations of their products at any one of the thousands of independent men’s stores that were then fixtures of American downtowns.

On the other hand, the mass marketization of the Ivy League Look undermined its cachet. Status is linked to scarcity—of knowledge as well as of physical objects. The transformation of the Look from an aesthetic code understood by graduates of a few schools and universities and obtainable from a handful of merchants into a widely accessible uniform meant it no longer differentiated the right sort of fellows—described as “shoe” at Yale, reflecting their intentionally perverse habit of wearing white buckskins in all weathers—from the rubes.

To help students from newly diverse backgrounds, by the 1950s colleges were distributing lists of recommended clothing that were simplified versions of the J. Press catalog. Even without the wave of informality that continues to swamp us, that spelled the end of the association between the Look and high fashion. You can observe the shift in the historically meticulous costumes in the film adaptation of The Talented Mr. Ripley, set around 1955. Ripley, who only pretends that he attended Princeton, wears the heavy fabrics and muted colors to suit a New England autumn. His beau ideal Dickie Greenleaf, who is to the manner born and relishes the Mediterranean sun, prefers pastel beachwear and the Roman tailor Battistoni.

Japan’s fascination with the Ivy League Look began during the postwar occupation, when Americans personified modern democracy. But when a team of Japanese fashion photographers toured Ivy League campuses in 1965, they were horrified to discover that students wore shorts or corduroy jeans, untucked shirts, and anoraks or windbreakers on all but the most regimented occasions. They produced the photo book Take Ivy, which documented the trends of the time. The volume has since become something of a fetish object for menswear enthusiasts, and it captured the continuing practice of integrating casual and activewear. But the results were very different from the expected pastiche of Anglophilia and varsity sports.

Contrary to all expectations, though, the Look did not die. One lineage culminates in the brand of “prep” that reconstructed Ivy in lightweight materials and shocking colors. Another mutated into the dismal ubiquity of business casual, which extracted the most utilitarian aspects of the Look and offered them in the cheapest and least distinctive possible versions. A third branch, diminishing but extremely stubborn, refuses to change anything whatsoever, facing the Biden administration in garb unaltered from the Eisenhower years. None of these constituencies is especially appealing, either as a financial proposition or aesthetically. There’s a reason why the bulk of J. Press’s sales are in Japan (there are only two locations left in the United States).

Still, because it was so casual to begin with, Ivy remains the most wearable form of traditional clothing. While the sharp lines of classical tailoring have begun to seem anachronistic, the gentle slope of a J. Press shoulder is still inconspicuous. It helps that tweed, corduroy, and the other rugged materials that were central to the Ivy League Look work well with the denim, cotton flannel, and suede of haute grunge. J. Crew, whose very name is an implicit tribute to Press, has built a weakened but surviving empire on that liaison.

Ivy also remains appealing to new generations of clothing enthusiasts. In addition to aging diehards, younger men with the taste and wallets to buy good clothes continue to adopt the Look. Richard Press’s role at the company that bears his name is partly an effort to appeal to these customers, who are intrigued by the history but weren’t brought by fathers or grandfathers to the old York Street store to buy their first suits. His efforts are probably helped by other writers and publicists who remind their audiences that Ivy was never just for the Ivies. The recent book Black Ivy: A Revolt in Style by Jason Jules and the podcast series Articles of Interest by the broadcaster Avery Trufelman are two examples. The British firm Drake’s and other concerns have also found a niche selling lightly updated versions of Ivy staples.

Above all, though, Ivy remains a plausible answer to one of the minor but recurring dilemmas of modern life. What can I wear to look stylish, even elegant, but not like a jerk? The sleazy confections of the Seventies look bizarre, and the bold fashions of the Eighties have become ludicrous. Now that the infamy of the prep has receded, no one is likely to object to the old classics, pretty much as Oliver Barrett wore them. The situation is nowhere near the mass market of the middle twentieth century, but it is perhaps not so different from the specialized service for a demanding customer with which the Look began.

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