I have to tell you, I’ve never seen a genre of clothing so contentious as prep and its related cousin, Ivy League style. In just the past week three articles have posted that wrestle with the now-problematic legacy of traditional American clothing.
In a feature on J. Crew from the current issue, Vanity Fair addresses the brand’s original upper-middle class image, and links its financial troubles to veering away from this original vision:
J. Crew was born in 1983, three years after Lisa Birnbach crystallized the world of boarding school, Top-Siders, and pearl-wearing Muffys in her seminal Official Preppy Handbook. Founder Arthur Cinader conceived J. Crew as a chicer women’s alternative to newly successful cataloguers Lands’ End and L. L. Bean—that would sell the Ralph Lauren look at half the price. Ralph had already laid claim to the landed-gentry sport of polo, so Cinader settled for crew, added a J for flourish, and shot the first catalogue at Harvard’s Weld Boathouse, home of the women’s crew team. J. Crew has always been about context, and viewed in the bosom of casual privilege, simple roll-neck sweaters, weathered chinos, and rough-hewn barn jackets spoke to Ivy Leaguers and aspirants alike. The brand became, as The New York Observer once noted, a “proselytizer for the sun-splashed, ruddy-cheeked American Dream”—in an America that extended precisely, according to a 1989 catalogue, from “Kennebunk to Nantucket, Narragansett Bay to Amagansett, and points South and West.” (South and West being, presumably, Connecticut.)
Over the years, countless style tribes have adopted, deconstructed, and reconstituted whatever “preppy” means, but at its core, J. Crew has always implied collegiate, polished, privileged. The narrowness of the world the company first opened a window to is now, thankfully, a thing of the past. There is no one way to look or dress “American.” So how do you resuscitate a brand built on this definition? And is there still room for it?
Then this week Esquire announced that preppy is back “but completely different than you remember,” which suggests that if it’s completely different, it’s probably something else. In fact, Esquire all but says as much:
Say the word “preppy” and it’ll very likely conjure images of John F. Kennedy, early aughts Vampire Weekend, and maybe your favorite Vineyard Vines-bedecked finance bro. Preppy is, after all, short for preparatory, as in school, as in East Coast WASP factories churning out Wall Street bankers and ‘80s teen movie villains. But while the word may come laden with more than a few negative connotations (at least for some), the style itself has exploded well beyond its elitist past.
Over the last few years, a smattering of savvy menswear brands have taken what was once the provenance of Ivy League schools and East Coast regattas, and infused it with strains of skate, punk, hip-hop, and downtown grunge to create something far cooler, and far more inclusive. Not that prep style hasn’t pushed beyond its WASP borders before. But this time, things are much more ambitious. This is more than just the appropriation of a rugby shirt. This is a full scale re-imagining of what prep means. It’s prep for the people—all people—where navy blazers and popped polo collars are just as likely to appear alongside dreadlocks and hyped-up sneakers as rowing teams, polo clubs, and guys named Hoyt. It’s two pairs of boat shoes coexisting on two very different sides of the prep continuum.
Since the middle of the 20th century, Ivy-prep has served as a cosmos in miniature for America’s culture wars. Originally developed by the WASP establishment, it was later adopted as the uniform of a middle-class everyman, then cast off by hippies, rediscovered in the age of Reagan, and has sped through several iterations over the past two decades. The latest issue of contention centers around “authenticity,” which seems to be a euphemism for the fact that it was WASPs who developed both the style and the institutions — Ivy League colleges, prep schools — for which the genre of clothing is named. Authenticity has emerged as the watchword for new fashions: the more of it you have the better it will sell. Unfortunately, “authentic” can also carry all the problmatic baggage of the past.
Derek Guy, contributing writer at Put This On, recently addressed the problem of authenticity in prep clothing and seems to imagine that a battle is emerging over who is entitled to wear tradition, which may be primarily a reflection his own personal issues. In “Prep’s Perps: A Look At Prep’s Issues With Authenticity,” he argues that some nefarious preppies are appropriating the style. The vitriol behind the piece actually caught me off guard, and I began to wonder if something more might not be going on. A search of prep and Ivy related articles on Put This On and Guy’s personal site, Die, Workwear, reveals a clotheshorse who is appreciative of preppy style, but, since the 2016 election, is increasingly haunted by the idea that this style he admires is being worn by the bad guys.
In fact, his concerns are not surprising when properly put into context. Starting in the late 1960s, Ivy Style clothing was viewed by campus radicals as the purview of conservatives alone. In a recent podcast for The Hogtown Rake, G. Bruce Boyer recounted his experiences as a well dressed young college man in the era of Vietnam and the Civil Rights Movement. He was interested in New Left ideologies, but inspired fear and resentment from his fellow students for wearing what they perceived as the clothing of the establishment. It was believed by young leftists then that clothing signaled one’s political orientation, and tailored clothing meant conservative, whether or not Boyer himself belies that assumption. It would seem that, at least to campus radicals in the ’60s, clothes really do make the man — and whether he wants to be made or not.
The association between the Northeastern elite and prep lives firmly in a semi-mythical past. Prep and Ivy have been the American uniform for varied classes and races since it first emerged as a fashion trend in 1954. The items comprising the Ivy League Look didn’t have to change in order for African Americans to wish to wear them. So rather than the privileged tribal identifier that Guy believes them to be in 2019, prep and Ivy clothing have served as a democratizing element available to anyone with the taste for wearing them. The question of whether we should be authentic to an era of inequality is shown to be tendentious. White presidents, black musicians, office workers, and college students of all races could be found in Ivy and prep clothing during the heyday, and associating the look with a few bigots of past or present is pure guilt by association. Thus the culture war in which Guy seems to believe prep is yet another battleground — with Jack Carlson versus Tucker Carlson —is in fact far subtler than he might have been imagined. It isn’t merely a conflict between ideologies, ideas, and the bounds of appropriateness, but a conflict over the meaning of things that we all agree we want. Guy’s peculiar disdain for the often conservative, and occasionally backwards, remarks among Ivy Style’s 49,000 approved comments reveals him to be a partisan in this supposed battle, fighting for control over the meaning of the clothes he enjoys. Except that this battle largely exists only in Guy’s Trumped-up imagination.
A friend of mine once remarked to me that prep is “just clothes.” The more I look into the past of Ivy-prep, the more I see the truth of that claim. The style is, in fact, not solely the product of privilege. It might not even be primarily the product of privilege, unless you think every guy who burns in the sun is privileged. It could never have become a fashion trend if it had been. Fashion needs the approval of middle-class dollars to become trendy. But perhaps for Guy all stench of impurity must be expunged in order for him to enjoy prep, lest one become guilty by association with old guard elitism. One wonders what opinions might pop up in Put This On’s comments section, if it had one. — PANI M.