The Preppy Look

Published in the Nostalgia feature of Vogue, November, 2004.

I arrived at Yale on a late-summer day in 1977. I was wearing a grass-green T-shirt with a green gingham collar and placket, and wide-legged jeans with front patch pockets. I had taken a red-eye from San Francisco, and I was tired and sweaty as I struggled to get my numerous suitcases from the bus stop to my dorm.

But it wasn’t a dorm. At Yale, things had names that were distinctly east coast to me—distinctly other, and therefore glamorous. I wasn’t headed for a dorm, I was headed for Farnam Hall, a “freshman residence” located on the “Old Campus.” Farnam was affiliated with Jonathan Edwards, the “residential college” I would move to as a sophomore and inhabit for the rest of my time at Yale. Jonathan Edwards, or J.E., as it was called, was a gothic enclave with its own courtyard, library and cafeteria, though the cafeteria was not a cafeteria, it was a “dining hall,” and the lounge you traversed to enter it was a “common room.”

The people were east coast, too. More, they were a kind of east coast I’d heard of in certain books and movies but never encountered myself. Said Ryan O’Neal to Ali MacGraw early in Love Story: “What makes you so sure I went to prep school?” For many years, that scene had glowed in my mind, alongside aspects of other movies and of books, and by the time I arrived at Yale I had a well-furnished sense of what it meant to be a preppy: great wealth, of course; “blue” blood (whatever that meant); a familiarity with sports like lacrosse and field hockey, which we just didn’t play in California; and, most of all, an enviable feeling of belonging to the right world. In my mind, all of this somehow lived in what I’d heard preppies wore: red twill pants, polo shirts with the collars turned up, topsiders from L.L. Bean.

But there was far more to it than that. As an Ivy League freshman, I discovered dozens more sartorial symbols of preppydom than I’d ever have guessed existed. There were blucher moccasins, sort of a thinking person’s topsider. There were neckties with little sailboats on them. There were Oxford shirts in pale pink and yellow. Preppy girls had their own look, which included skinny tortoise-shell hairbands, small pearl earrings, and, most strangely and intriguingly of all, cardigan sweaters worn with the buttons in the back. When, not long ago, looking through some very old issues of Vogue, I saw a photograph of a confident, sleek-haired co-ed wearing not one but two shetland sweaters, a kilt, and cabled socks…well, I was back in my freshman year. The photo may have come from the fifties, but little had changed in northeastern collegiate fashion in the decades leading to 1977.

Or had it? I was from California, true—the Summer of Love had taken place almost within shouting distance of my girlhood bedroom—but hippie culture, and therefore hippie style, had reached far and wide. I knew that. How was it that the Ivy League still looked like this?

What I understand now is that it didn’t. We see the world as we want to or as we must. Yale in the late 70s was incredibly varied—populated by hippies with flowers in their hair, studious types in full nerd regalia, jocks drenched in aftershave, Bowie wannabes with glittery eyes, and any number of “regular” people—but my Yale was filled with preppies, and it was the preppy world I wanted to join.

My task was clear. First, my jeans had to go. Wide-legged? Front patch pockets? Absolutely not. The only acceptable jeans were 501s, and I got a pair as quickly as I could, ignoring the fact that the difference in my waist and hip measurements ensured that they would not fit me. Preppy girls didn’t have hips, and so I would ignore mine.

Next, a Fair Isle sweater. My friend T. and I learned that there was a store called Talbot’s where such a thing could be acquired, and we boarded a bus for Hamden, a New Haven suburb that boasted a branch of this venerable establishment. Alas, the bus deposited us over a mile from our destination, and by the time we found the shop itself my blistered feet had come to seem to me an objective correlative of my fashion problems.

But I persisted. For those blistered feet I bought clogs and penny loafers, and, with winter coming, boots from L.L. Bean. I bought a tan corduroy blazer (one of the ugliest garments I have ever owned). I bought a pleated skirt, even though I hadn’t worn a skirt since seventh grade.

Somehow, though, try as I might, I was always a little bit off. My shetland cardigan didn’t have the right grosgrain ribbon. The cotton turtleneck I wore underneath it had a too-tight, too-tall neck. Even those L.L. Bean boots: I should have ordered the ankle-height kind, like everyone else had. Why couldn’t I look like the people I emulated? Why couldn’t I join them? My otherness went beyond what I wore, of course—I had not grown up “summering” anywhere; I had not learned, at Choate or St. Paul’s or Miss Porter’s, to be sardonic; I didn’t have a Mayfloweresque middle name—but I convinced myself that if I could just get the fashion part right—if I could just find out where the preppy girls got those looser neck turtlenecks—perhaps I would finally feel comfortable.

Growing up is universally acknowledged to be one of the most necessary and difficult things a person can do. Or is that “must” do? What I wonder is: how do we know when the job is done? When are we grown up? One answer is when we have children. Another is when we lose our parents. When we buy a house. Start a (401)k. Respond to the dentist’s reminder card by scheduling a cleaning. Certainly, when we stop wanting to be different from what we are, and when we finally understand that all around us people are struggling, often when it’s least evident.

I would like to suggest that another marker is this: that we are grown up when we find a personal style. I don’t mean anything like a uniform, although for some people that’s exactly what happens. (Think of the woman you know who has five polar fleece vests, which she wears in combination with five pairs of drawstring pants; or the man who sports a striped shirt and micro-patterned tie day in and day out.) I mean something broader, a sense of knowing the kind of thing one wants to wear, coupled with the confidence to choose what one likes and what looks good and is comfortable, rather than what everyone else is wearing.

This did not happen to me quickly, but some time after I’d graduated from Yalecand left my corduroy blazer behind—I began to shop not for whatever must-have item I needed in order to feel that I fit in with those around me, but rather for clothing that I loved. Jeans that fit me like a second skin, waist and hips. A soft cashmere sweater because it felt so good. A yellow linen skirt that was somehow a perfect breath of summer. Today, my closet is filled with garments that work for me, and there are entire seasons when I don’t buy anything at all, because I just don’t like the look. (There are others when I shop and shop, until my bank account screams for mercy.)

And what of that girl in the grass-green gingham-trimmed T-shirt? Climbing the stairs to her first home away from home, on a hot New Haven day? She enters her suite, greets her roommates, and then goes into her tiny single and kneels on her new bed. Out the window, her new world beckons: its marvelous, towering trees; its centuries-old buildings; its classrooms and its professors, who will teach her so much. In this world there are people she will meet soon and still love twenty-five, thirty, forty years from now. At this moment, though, what she sees, walking across the perfect grass, is a group of students who are talking and laughing and wearing exactly the kind of clothing she expected them to wear. She doesn’t know yet that clothes don’t make the woman, that contentment doesn’t arrive from the outside, a special sweater to put on that will change the way you feel in the world. She doesn’t know that she’ll get there a different way, to contentment: by following a long path she can’t imagine right now. In fact, she doesn’t know much at all. It’s a good thing she’s going to college.