LET YOUR MIND’S EYE WANDER FOR a moment. Let it come to rest on the prep, that venerable fashion icon who favours 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-sweater’ed 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 lawyer’ing, 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 colours that seem out of place in normal life: pinks or purples or bright greens. These made you “fun” and “crazy” and “interesting,” without you 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 and Polo’s 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 catalogues 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.