“Preppy” is a simple way of describing a style of dress associated with a type of American which is, tragically, “waning in Westchester” (as writer Joe Malchow puts it). The fashion belonged historically to the Eastern WASP establishment and so belonged also, in the public eye, to inherited money and privilege. The style took its name from New England college preparatory schools and the real preppies were the students there. Of those, the most authentic were the ones whose fathers and, for the luckiest, grandfathers had been students at those same schools, and who wore those old men’s faded, broken blazers and slip-on tassel loafers to class.
The legacies were the luckiest for having the old blazers and shoes because those things had a certain cachet, the way scuffed leather does, the way your wristwatch will never seem quite so adult and masculine as the one your father wore when you were young. That cachet was authenticity and authenticity was a badge which identified established families. The badge had little to do with money, although that was often a side-effect, but with taste: author Nelson W. Aldrich, Jr. notes “the preppy ideal represents a collective yearning, with respect to money: yearning for a triumph of class over income, of grace over works, of being over doing.”
The ideal was apparent in the rumpled old blazer’s being held in higher esteem than the shiny new one because it was rumpled from generations of tradition. The blazer, and the shoes, were investments: an initial outlay of cash for quality meant a lasting return. Sound investments paid off: briefcases lasted, country homes were passed down along generations, children moved into their parents’ houses. The essence of the style was a disdain for showy wealth, of new possessions, because newness meant first possession. A new blazer couldn’t have been worn by a father or a grandfather to the same school as its current owner, so its owner must be a newcomer.
Author and professor G. Bruce Boyer writes:
“It’s better to have one good pair of shoes than a half dozen cheap ones, because the cheap ones look cheap even when they’re new, but the new ones look good even when they’re old. Quality by definition is the best you can get for your money. If you buy a pair of shoes for $500 and they last you 10 years, that’s $50 per year. If you buy a pair for $100 and they last you six months, which was the more expensive? I think the Old Money WASP guys were just cheap, so they always bought the best.”
“And the best always is the cheapest, if you have the money to buy it in the first place. The way we do it today is ask how much it costs. Nobody asks how much it costs over its lifetime — it’s just the initial price. And if you only look at the initial price, you’re going to get screwed every time. I think that’s what the Old Money guys thought, and I think they’re right. New Money doesn’t understand the appeal of old, worn family things.”
The lesson here is two-fold: frugality and taste. Sound, conservative investments will be rewarding, and ostentatious displays of wealth are deplorable. The wisdom of the prep students was to invest in tried-and-true quality, to avoid flashy affectation, to find value in tradition. Their traditions were their badge much more than any money ever was, and current economic climes might remind the rest of us of the value conservative traditions can hold, in dress as well as finance, and of the importance of function over form, and of substance over style.