A couple of weeks ago we put up a tongue-in-cheek post about the difference between Ivy and preppy. That got us thinking around the virtual office, and so we present a double-shot of ruminations on the topic. First up is Ivy Style founder Christian Chensvold, while in our next post “Golden Years” columnist Richard Press will share his thoughts on style and semantics.

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When I founded Ivy Style, my editorial plan was to cover both the Ivy League Look as well as prepdom, seeing them as inextricably intertwined. Viewing Ivy and preppy as separate from each other seemed to me just as silly as the dubious assertion that there is in fact a legitimate genre of clothing (with a concomitant set of lifestyle values) called “trad,” or that the Ivy League Look was “all about marketing” rather than an expression of the tastes and culture of a certain segment of American society, another tired canard I’ve read on the Internet.

It always seemed to me that what we’re dealing with is hardly two things opposed to each other, but branches from the same tree, or to be more specific, different stages in the growth of the same branch across a timeline that reflects the ever-changing nature of fashion and society.

But let’s explore the topic further. First off, no remarks on any supposed differences between Ivy and preppy mean anything until the speaker first explains how he is using the terms. “Preppy” specifically has become both watered down by misuse as well as weighed down by the baggage of accumulated connotations. There’s little subjectivity involved in what the Ivy League Look refers to, so for expediency’s sake I’ll leave that one alone. But “preppy” today is a highly loaded term, and the way I see it its useage generally falls into one of three categories which correspond to different points in time over the last several decades.

The most watered-down useage of “preppy” is the current version. “Preppy” today is routinely used by the fashion industry and media to mean anything clean and classic, however tangential its relation to what was considered preppy a generation before. As I’ve mentioned previously, there’s a documentary called “People Like Us” in which a poor white kid from the Midwest uses the word “preppy” to refer to the moderately clean-cut Abercrombie-clad popular kids at his school. This is a far less specific usage of the word than in the book and film “Love Story,” in which it’s used by someone who knows whereof she speaks to refer to a rich Harvard student with a roman numeral after his name who actually attended a prep school.

The second common usage of “preppy” is in the post-“Official Preppy Handbook” sense of the word, when the look — much more connected to the ethos from which it springs — achieved national popularity in the early 1980s. The 1984 prepsloitation film “Making The Grade” is the perfect zeitgeisty example of this kind of preppy. The clothing consists of simple basics such as khakis, penny loafers and blazers, combined with Technicolor sportswear, and the movie is set at an all-boys prep school whose alpha preps are all to-the-manner born.

Finally we come to the sense of the word when it first entered the popular lexicon via the 1970 movie “Love Story,” culminating 10 years later with the publication of “The Official Preppy Handbook,” which, from what I can tell by having read about this topic, met a few old-school preps, and having chatted several times with Lisa Birnbach, is a pretty accurate representation of prepdom at the time.

“The Official Preppy Handbook” extols Brooks Brothers and J. Press, the chief purveyors of the Ivy League Look, so the difference between ’70s preppy and the ’60s Ivy that preceded it is pretty negligible. “Preppy” in the ’70s sense was essentially the same clothing that had been sold by the same Ivy League clothiers as sportswear or resort wear. As I reported in the go-to-hell story for The Rake, bright colors had been a part of the WASP establishment’s leisure wardrobe for quite some time. The pink Shetlands and madras pants we think of as “preppy” had been sold by Ivy clothiers long before the preppy era, and Ivy League staples such as natural-shouldered jackets, oxford-cloth buttondowns, plain-front khakis and penny loafers continued to be worn in the early ’80s under the name “preppy” when WASPy clothing again became popular.

The Ivy League Look fell as a popular style in 1967. “Preppy” came to replace the “Ivy League Look” as the ascendant term for what was more or less same style; the term was also used to describe the tastes, behaviors and values of prepdom’s chief arbiters, the upper middle class of the East Coast. In 1925 Fred Waring And His Pennsylvanians sang about being “Collegiate;” in 1960 Jan & Dean sang about their girlfriend being so “Ivy League” because her canvas sneakers were filthy; and in 1984 pop singer Cheryl Lynn released an album called “Preppie.” Nobody in the disco-duck ’70s or day-glo ’80s would call somebody “Ivy League” because he wore buttondowns and natural-shouldered jackets. The term had become passé.

The exceptions, of course, were in England and Japan, where a retro sensibility kept the term “Ivy” current among a small group of followers. But it was largely a backwards-looking style, especially in England. The Japanese worship vintage American Ivy clothing, but are also happy to produce their own updated Ivy-with-a-twist versions. The English also worship American vintage, but being orthodox Ivy adherents, their contemporary versions are copies of vintage specimens. There is no such thing in England as Ivy with a modern twist.

Now have a look at the photo below. Does this shot of J. Press in 1980 depict “Ivy” or “preppy”? We all agree that J. Press was one of the chief purveyors of the Ivy League Look, and yet the clothes in the photo are so… loud. Does that make them “preppy”? If so, and a single retailer could sell the same clothing referred to by different names in popular nomenclature, then perhaps they’re in fact the same clothes, with the different words used to describe them chalked up to changes in fashion and society.

But it wasn’t just the terminology that had changed. American dress had begun its long, seemingly bottomless descent from the formal to the casual, best exemplified by the approach to dressing for airline travel, which used to involve wearing your best clothes and now seems to encourage wearing your worst. An even more extreme occurred on college campuses. Jackets and ties were common up until ’67 or so and then all but disappeared, and college students today are one of the worst-dressed groups in society — one notch above the homeless and one notch below the guests of amusement parks. If a typical ’70s preppy outfit — khakis, penny loafers, bright polo and bright sweater — is more casual than a typical ’60s Ivy outfit — khakis, penny loafers, knit tie and herringbone jacket — it’s because it was a more casual decade for society as a whole.

Of course brands such as Brooks Brothers and J. Press resisted “preppy” as a description of their clothing just as they’d remained mum on “Ivy League” before and would likely chuckle today at the reference to their clothing as “trad.” They’ve been around long enough to see themselves as above the latest buzzword, and no doubt always will. — CHRISTIAN CHENSVOLD