The Prep Gets the Last Laugh

Forget what you think you know about whale belts and popped collars. Why now more than ever New England's singular sartorial aesthetic is the style for our times.

Illustration by Heather Burke

Let your mind’s eye wander for a moment. Let it come to rest on the prep, that venerable fashion icon who favors ribbon belts and bow ties; that Bostonian done up in tweed or seersucker. Doubtless you can envision this character, perhaps in his natural habitat on Beacon Hill, perched, perchance, at the bar at 75 Chestnut, in a striped button-down or a polo shirt with the collar casually popped. Maybe, in your mind’s eye, you see him greet a fellow prep with the ritual handshake of an ancient secret society, see them reminisce over ancient squash games partaken, no doubt, on the grounds of some ancient summer home. The prep’s pastel clothing, his Clinton-era Saab, his disdain for socks—it’s all so easy to mock.

But what if you looked closer, past the stereotypes and the gaudiest pink-sweatered goofballs? What you’d find is a lifestyle that belies the pompousness that’s so repugnant to so many. Because though it was long ago co-opted to sell marked-up madras to the wannabe masses, the prep culture invented in New England—real prep culture—is at its core driven by good old-fashioned Yankee thrift. It’s about patching rather than replacing, about worn-in rather than shiny-new as status marker. Which is to say that, as our economy continues to sputter and we grasp desperately for what’s familiar and comfortable, maybe the prep had it right all along.


The origins of the distinct aesthetic we call “prep” might be summarized thus: For generations, well-off denizens of the Northeast passed family money down through long-held investments, padding it with lucrative careers in lawyering, doctoring, and investment banker-ing. When members of this prosperous caste married and bore children, they sent their young to the same preparatory schools they themselves had attended. These schools had dress codes, and said codes involved, for boys, a uniform of coat, tie, and khakis. To distinguish yourself, you wore your clothes decidedly broken-in, the faded fabric of your trousers or blazer suggesting you were wizened and all-knowing. Alternatively, if you were sufficiently brazen, you made yourself noticeable by donning colors that seem out of place in normal life: pinks or purples or bright greens. These made you “fun” and “crazy” and “interesting,” without your actually having to be any of those things. After graduation, the young prep would take his well-honed sartorial sensibility to college, where he was given alcohol and, by senior year, an in for a job in Boston (on occasion he and his brethren would wash up in Connecticut or the WASPier regions of Long Island, too). He’d go on to marry and sire a brood of preppy kids. That was just how such things went.

By the time of the Reagan administration, Lacoste polos had become a mainstream look. The hoi polloi had decided they wanted inside the prep bubble. In 1980, The Preppy Handbook, a slender, whimsical field guide, spent 38 weeks atop the New York Times bestseller list. By the middle of that decade, the style had permeated throughout popular culture, finding a standard-bearer in Alex P. Keaton, with his sport coat and penchant for supply-side economics. Noteworthy here is that Michael J. Fox’s Family Ties character and his real-world counterparts began to blend the old austere prep aesthetic with the shameless materialism of the greed-is-good era. Prep became synonymous with the more easily loathed yuppie (a curious convergence, considering the frugality underpinning genuine Brahmin culture).

When the yuppie golden era ended with the recession of the early 1990s and pop culture lurched toward an emphatically un-prep moment of flannel shirts and unwashed hair, prep did not die; it was once again merely tweaked. Brands like Polo stepped in and further democratized the look—spreading it to shopping malls near and wide, to be purchased by grunge agnostics—while at the same time reemphasizing and recasting its elitist undertones. The iteration of prep envisioned by Ralph Lauren catalogs whisked you away to the stables of English manors, a place adorned with riding crops braided of the finest Italian leather—but also one where horse-emblazoned shirts and reasonably priced chinos could nonetheless be had for a non-aristocratic sum.


Lost on those who had co-opted the prep look as shorthand for insufferably rich was any knowledge that the style had its roots in pragmatism. For example, in popularizing the popped-collar tennis shirt in 1927, tennis star René Lacoste was just avoiding the restrictive dress shirts normally worn on the court, while at the same time protecting his neck from the sun. Nantucket Reds, the ruddy boat pants that have become a seminal prep garment, share similarly utilitarian roots. Philip Murray of the island’s Murray’s Toggery Shop began stocking them shortly after World War II. The cloth was hardy; the brick-colored dye less so, fading with each wash. Murray christened his pants Nantucket Reds, which encouraged tourists to buy a pair as a memento of their island vacation. Of course, on the legs of locals, the sun and salt would go to work on that dye and swiftly reduce it to a dull salmon hue, signifying to the country club crowd that the pants’ owners were longtime summer citizens of Nantucket. As with the prep school blazers, wear and tear denoted status. (This is why the Toggery Shop website notes that “customers have been known to take all sorts of measures to attain the faded pink immediately.”)

Yes, it’s all a bit silly—but sillier than buying an empire-waist dress because it’s trendy, only to have it mostly give the appearance of being pregnant? Isn’t there something reassuring about owning clothing that you know will be better-looking next season, and better still the season after that? Vineyard Vines cofounder Shep Murray thinks so—he’s betting his expanding prep-fashion chain on it. “Now more than ever, people are going back to basics. You aren’t going to see people going out to a lot of fancy restaurants. You’ll see them sitting around a friend’s kitchen table, and our clothing is appropriate regardless,” says Murray, who opened a big store in the Pru last October. “Let me put it another way. This style of clothing says that you have taste and confidence without having to hide behind the expensiveness of a brand to show it. If you’re into this stuff, you’re probably not driving a Ferrari.” Murray’s brother and business partner, Ian, chimes in. “Yeah, more like a rusty old Volvo.”

A certain acquaintance of mine, who can trace her Hub roots to the days when the Back Bay was still a bay, is precisely the sort of person the Murray brothers have in mind. “The entire lifestyle is positioned around sitting out the bad times and downplaying the good ones,” she says, and laughs. “And anyway, most of these old families have all their money tied up in their big, empty houses. They’re not exactly trading in derivatives.”

To its old-school devotees, prep culture isn’t a pompous affectation. It’s a cultural bomb shelter, a comfortable place to crawl into with a Lilly Pulitzer bedspread in order to wait out the storm. Compared with the fashion fools who for years have winged toward fads like moths to a flame, the presumptively anachronistic prep suddenly looks like a trailblazer, a (very) early adopter, in the Gladwellian parlance.

Sure, we cling to some strange notions in Boston. There’s a reason people from outside the Hub can’t understand why the city’s most desirable place to live still features doorways designed in an era when men were 5-foot-3—or, more to the point, why so many of the people who live in those houses, people who sit atop our social ladder, blithely ignore most fashion trends. (Suck it, Ed Hardy! You lose, Christian Audigier!) But lately that impulse has seemed more and more like one worth emulating. If this recession causes Yankee values to reassert themselves via our closets, it won’t be such a bad thing. Trust me when I say that we’ll be glad to be reminded what a prep really is.


Contributing editor Kevin Alexander, the Boston editor of Thrillist, does not own a pair of Nantucket Reds.