An Education

A Midwestern Girl Goes to the Ivy League

Harvard Yard in the 1990s

I remember the first time I saw her, this young woman who would come to symbolize everything I once coveted and the superficial part of myself that I later grew to despise. It was early 1995, the spring of my freshman year at Harvard. I was sitting in an economics discussion section. She barged in with all the insouciance and entitlement of the cosseted 19-year-old she was, and, oblivious to the other students sitting there, began talking to our graduate-student instructor about a makeup test.

I remember my surprise at the blithe, confident way she owned all the space and time in the room. But it was her clothing, casual yet unmistakably expensive, that transfixed me. I was a financial aid student from suburban Illinois; in 19 years of avid mall-going, I’d never seen anything quite like these garments. Her cabled gray sweater was made of such surpassingly fine cashmere that it looked soft, like she was wearing a cloud. Her designer jeans grazed her ankles in a feat of perfect tailoring, and each of her buttery brown loafers was adorned with a gold bar. (These were the iconic Gucci horse bits, but I had yet to figure that out.) Around her shoulders she'd draped a pashmina the color of Pepto-Bismol. Cashmere atop cashmere: Did it get any better than that?

I’m not exaggerating when I say that seeing her precipitated in me an irrevocable shift in perception, not unlike the sort that can be induced by travel to a jarringly foreign place, or hearing a devastating piece of gossip, or taking psychotropic drugs. I had certainly seen my share of rich kids during my first semester—Harvard was crawling with them. But I was shy and, anxious about my ability to keep up academically, I’d hardly socialized, spending most of my free time alone in the library. This meant I hadn’t interacted with many of these students (or, in truth, with many people at all), and I definitely hadn’t had the chance to examine one up close. In that moment, as I observed her, an epiphany that had slowly been forming suddenly crystallized for me: The world was a far more complex and impenetrable place than I had ever realized, full of mysterious and pricey objects I had never seen, and didn’t even have the language for.

Not long after, another member of what I would come to think of as the Gucci Loafer Mafia—a dark-haired, effete, and ostentatiously wealthy South American guy whose father was an ambassador—introduced me to her. Let’s call her Jessica. She invited me out to dinner. I viewed this gesture as extravagant, intimidating, curious. Were there undergraduates who dined out? With the exception of sharing the odd late-night pizza with my dorm mates, I ate my meals in the cafeteria. But I soon found myself on a friend date at a Japanese restaurant in Harvard Square.

Up close, in a black riding blazer, starchy white shirt, diamond studs, and a pair of vintage tortoiseshell glasses that were round in the way that was chic before Harry Potter came along, she mesmerized me. She wasn’t particularly warm or friendly—her face had a sour, pinched look, like she’d just received unfortunate news—but she was clever and worldly, with an inexhaustible cache of charming stories about trips to places I’d never visited and celebrities I’d only read about, like Ivan Reitman and Shoshanna Lonstein. But mostly, I’m chagrined to admit, I was fascinated by her aura, for lack of a better word, which was ineffable but palpable. She carried with her an atmosphere of enviable ease that hinted at private tennis lessons, personal shoppers, and immunity from ever having to make your own bed.

It was a life so exotic to me that I couldn’t really imagine it, but I could sense it, like a subdued but heady and ever-present fragrance. It was there in the bored, heavy-lidded way she listened (or didn't) while you talked. It was evident in her arms, tanned from Bahamian vacations and muscled from water aerobics in her parents’ pool. (She had toned her body to its absolute racehorse extreme; I would later suspect this is why she always looked pained.) It was there in her voice, low and throaty and calibrated for charismatic effect; she seemed to luxuriate in its cadences. “It was full of money—that was the inexhaustible charm that rose and fell in it, the jingle of it, the cymbals’ song of it,” Nick says of his rich cousin Daisy’s voice. I’d reread Gatsby that fall, and when I heard Jessica speak, Daisy sprung instantly, banally, to mind.

Did I want miso soup? Shrimp shumai? Sashimi? I wasn’t sure; I didn’t know what any of it was. Months earlier, I had undergone a similar initiation in the university cafeteria, where I’d eaten my first fresh pear—I’d only had them canned—and learned what hummus, falafel, tahini, and tempeh were. But those were silent, solo mini-humiliations, not endured while seated three-and-a-half feet from an impeccably dressed rich girl I wanted to impress. “Yes,” I told her. “Let’s get it all.”

In June, when school let out, she invited me to come visit her. Using money saved from working two summers as a nanny, I bought a ticket and flew to New York for a four-day weekend. “Park Avenue,” I told the cabdriver at LaGuardia. I felt glamorous just saying it. As I rode across the Queensboro Bridge into Manhattan for the first time, the hot midday sun glinting off the skyscrapers like all the brilliance and ambition of the city made manifest, the buildings and stores and restaurants and the infinite possibilities they represented piling up as we passed, I felt a surge of euphoria. This was where I wanted to be, at the beating, blood-pumping heart of urbanity, culture, and sophistication.

Her apartment building was a stately old prewar on the Upper East Side. When I arrived, a doorman relieved me of my Samsonite and led me ceremoniously to the elevator, stepped in behind me, and ferried me upstairs. I expected a hallway lined with doors to other apartments. Instead, the elevator opened directly onto a massive, sumptuous living space decorated in tasteful colors and regal furniture. The carpeting was the kind of flat, low-pile, wall-to-wall broadloom—none of that shaggy suburban stuff—that lends a place the air of an English aristocrats quarters. The draperies were heavy and ruched. I had the surreal sense of walking onto a movie or TV set. The only person I’d ever heard of owning an apartment that spanned a full floor was Philip Drummond on Diff’rent Strokes.

A maid led me to Jessica’s room to wait for her to come home. Alone in her bedroom, which was eerily neat and free of human clutter, I could hear the street noises of Manhattan below: the occasional bleat of a horn and the heavy sigh of truck brakes. From where I sat on the bed, I could also see a black suit jacket hanging from a wooden hanger on the closet doorknob. The price tag was still attached. Terrified she would walk in and catch me, but pulled along by my curiosity just the same, I scooted to the edge of the bed and grabbed hold of the sleeve. $1,600! It was more than I had ever paid for anything in my life. To put it in perspective: During my first year of college, my mother, who supported my two younger sisters and me by herself, was barely making $50,000 a year.

Jessica materialized in the doorway, yanked a packed leather weekend bag from the corner, and announced we were setting out for the Hamptons, where her parents owned a house. Downstairs, a doorman was standing in front of an idling Mercedes SUV. As we drove from the Upper East Side through East Harlem, Jessica confidently at the wheel, I found myself as shocked by the poverty and urban blight I was witnessing as I had been by the price of the jacket. “Tulips to train tracks,” Jessica said aloud, not really to me, as we zoomed past, graffiti and garbage and vacant lots blurring out the window.

If I were a different sort of person, someone who did not derive an uncomplicated hit of pleasure from an elegantly cut dress or a well-designed object, I wouldn’t have been so susceptible to her. For years, I’ve felt a nagging sense of shame about this skin-deep side of myself, as though it were a personally damning quality—a secret I should never admit to, like an Internet porn habit or a tendency to pick one’s nose in private. As I was writing this essay, I confessed my moral queasiness to an old college friend who happens to work as an adviser to first-generation college students at an Ivy League school. She told me that no matter how much her students have achieved or what hurdles they’ve overcome to get to college, many of them, particularly the young women, feel depressed and isolated when they can’t compete in material terms with their wealthy classmates. “It’s normal to want to fit in with your peers at any age, but especially at 18,” she said, pacifying me. She then surprised me by revealing that she, too, the child of Upper West Side sophisticates, had been plagued by feelings of inferiority. And yet I still believe that a blizzard of personal factors converged to make my case something of an extreme one.

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MY PARENTS DIVORCED when I was six. For years after that, my mother never had much money—we were solidly lower middle class—and yet she always placed a premium on appearance. A well-groomed exterior, she believed, signaled equilibrium within. This is a woman who will look at you, no matter how bone-tired or in despair you are, and cheerfully suggest you put on some lipstick. Even in the lean, chaotic years after my parents’ divorce, she managed to find flattering dresses on deep discount to wear to her corporate job, and she was endlessly engaged in decorating our home, especially after she was promoted from executive assistant to midlevel manager. “Why are there always little squares of fabric all over the place?” my high school boyfriend once asked, referring to the swatches lying around the house: material evidence of my mother's belief that re-covering our furniture and re-curtaining our living room might renovate our lives.

Maybe it was her influence, or the countless teenage hours I spent poring over Sassy magazine and roaming the mall in search of trendy sale items, but I’d somehow formed an idea of myself as a person with exceptionally refined taste. I didn’t have bad taste per se; like my mother, I’d always had a good eye and an innate sense of color and proportion. But my aesthetic sense was nevertheless unschooled and underdeveloped. Upon meeting Jessica and girls like her, I felt embarrassed by how little I’d been exposed to. You might say that Jessica activated my latent inner aesthete.

Looking north up Park Avenue

Or my latent inner snob. “Glamour…” Virginia Postrel writes in The Power of Glamour, her thoroughgoing exploration of the subject, “focuses and intensifies a preexisting but previously inchoate yearning.” Indeed, I trained my teenage fantasies of living a more cosmopolitan life on the wealthy young women I was meeting. Their cashmere sweaters and Gucci loafers were not only aesthetically pleasing objects; to my mind, they were evidence of a glitteringly superior existence. One where politics and ideas were discussed at dinner parties or in the sauna at spas, where boarding schools hired writers-in-residence to teach, where young people “took a year off” to travel. Obviously one’s ability to purchase Italian cashmere is wholly unrelated to how cultured or literate one is. But you couldn’t have told me that at the time.

I became an amateur cultural anthropologist, fluent in the behavior and accoutrements of Jessica and her friends. They lived on Park or Fifth Avenues or somewhere in Europe. They attended a handful of elite boarding schools or illustrious Manhattan high schools—the names came up so often they became a part of my vocabulary—and went to summer camp together, in the Catskills or the Adirondacks. Their fathers worked in finance. Their mothers were active in charity. Oddly—to me, anyway—they each referred to their own mother and father without the possessive (“Mom is coming to visit this weekend”; “Dad said to apply…”), as though their parent was familiar and universal, the only mom or dad in the world. They spent their holidays in the Hamptons, the Bahamas, Aspen, Vail, or Ibiza, where they learned to ski, golf, or play tennis—the rich-kid sports. They carried Prada backpacks and Longchamp bags, wore L’Eau D’Issey perfume, Cartier Tank watches, and those Elsa Peretti necklaces with the round, flat diamonds. The men owned their own tuxedos. Of course, nowadays, 20 years on, I no longer peer at these girls through such a smudged and slanted lens, and I understand that the über-rich don’t sweat these brand-name purchases any more than I stressed about a pair of Keds. In their view, such items weren’t extravagant—and buying them wasn’t necessarily displacing other spending, like, say, contributing to charity—they were altogether quotidian.

The ludicrous ways I behaved in response make me cringe now. It’s actually difficult for me to write about. I wasn’t going to share tales of summers spent working at the dry cleaner or hanging out in the Taco Bell parking lot, so I said very little about my background. I didn’t make up stories—I’ve always had a constitutional aversion to lying—but I did emphasize certain facts and omit others, allowing people to fill in the blanks with their own assumptions. I had in fact gone to Paris with my French class during my junior year of high school (we raised money by selling croissants), and I talked about that (minus the croissants). I had taken ballet classes. I had gone to camp. Sure, it was YMCA camp in Appleton, Wisconsin, but I left that detail out. My mother, I said, worked in marketing. (She did.) My dad was a lawyer. (He was.) Never mind that he wasn’t around much, and had disappeared when I asked him to help pay my tuition, refusing to fill out the financial aid forms.

My nasally Chicago-area twang made me a source of constant amusement and the target of much teasing (“Say that again!”), so I studied the elocution of these upper-class girls, intentionally shortening my vowels and locking my jaw. When I returned home on break, my sisters made fun of my “weird” manner of speaking. And then there was my wardrobe. I bought myself two pairs of dressy black pants, a passable black blazer, and, at T.J. Maxx, a black leather calfskin purse by a designer called Johnny Farah. That became my uniform. For variety, I haunted sales and outlet stores for whatever brand-name items I could find—a visible logo was ideal. I didn't own any real jewelry, so I didn’t wear any, and pretended my austere look was a choice. It was all carefully calibrated.

Clearly I felt insecure, inferior, and out of my element that first year at college, when every day presented unfamiliar experiences, foods, even words. (My friends laughed for days when I told them I didn’t know what a phallic symbol was.) And I guess I subliminally thought that imitating the ways of these girls, or convincing people that I came from a not terribly dissimilar background, would elevate me in my own mind, if not alleviate my situational discomfort. One could argue, of course, that the entire point of attending an Ivy League school (in addition to, well, learning something), and the reason such schools are generous with financial aid for students like me, is that the education and eventual opportunities that come from it might appreciably change your life circumstances, and your achievements might in turn have a positive influence on society. But I was 19. I wasn’t exactly taking the long view.

Occasionally, my pretensions came back to bite me, reminding me that these women were part of a tight, insular society as closed to outsiders as any religious sect. There was the weekend when a pretty, generally pleasant girl in my dorm, one whose father was a famous 1980s financier, told me she was leaving for a weekend of skiing—would my roommate and I mind retrieving her laundry from the dryer, folding it, and leaving it on her bed? I told her I was headed to the library, but I probably should have told her to fuck off. Or the time I spent an afternoon helping another New York girlfriend tweak her résumé and write thank-you notes to interviewers. “Amanda,” she said, looking at me in total earnestness, “you’re so smart. I wish you could come work for me when you graduate.”

Toward the end of college, like a heroine in a Victorian novel, my fortunes shifted—slightly, anyway. My grandfather, a retired scrap-metal trader who had invested in a gambling boat, sold his stake and gave me a few thousand dollars. I was supposed to use it for school expenses, but I took a chunk and bought a gold necklace with a tiny chip of a diamond dangling from it—a bid to compete with all those Elsa Perettis, and an amulet of sorts.

Almost as soon as I’d made this silly, pathetic purchase, forces began to conspire to teach me a few key lessons. There was the elementary and obvious one, that cash isn’t commensurate with taste (it is, in fact, often inversely proportionate to it), which I learned when I applied for a research grant and spent a summer in France, where the women dressed with label-free panache. But there was also a deeper, more essential truth: Beautiful things are alluring, and there’s nothing wrong with being drawn to them, but this attitude can also be a kind of trance in which you devalue your own life and forget your own good fortune—like being able to go to college at all. I came to realize the difference between enchantment and envy: The latter causes you to lose sight of what you have yourself.

Upon graduating, I got a job at a magazine, published a few small pieces, and began to hang out with friends who were artists and writers, all of which taught me that what I truly valued was nothing very temporal: creativity, ideas, freedom, art. At the magazine, a young woman who was as secretive about her affluent upbringing as I had been about my modest one sat in the cubicle next to mine. As I got to know her, she opened up about her family, her background, her money; she was so irreverent, and so tortured by the same twenty-something stuff I was—creepy men, drunken escapades, weight and body issues—that I couldn’t idealize her privilege. And then I fell in love with an artist, a photographer who wore thrift-store cardigans, lived in a converted Williamsburg warehouse, and had unmitigated contempt for my status-consciousness. One night, he went through my closet, good-naturedly scoffing at pretty much everything I’d acquired during my college years. How, I wondered, could I ever have thought that a designer bag was indicative of anything other than the money to buy it?

But the universe, as it were, decided to kick its message home. One night, I invited this boyfriend and two other friends—one of them my wealthy cubicle-mate—over to my studio apartment, where we got drunk on vodka and talked. The necklace was catching on my sweater and bothering me, so I took it off and set it on the window ledge near my bed. The following morning, I noticed it was missing. I searched every surface and cabinet and coat pocket in the apartment, but it wasn’t there. I couldn’t believe that any of my friends would take it, but apparently one of them had. Distraught, I tried to convince myself that it had just dematerialized. I was never supposed to own it in the first place. Either way, that lovely, delicate, but utterly pretentious necklace was gone. After a time, so was the girl who had needed it.

—An earlier version of this essay appeared in Elle Magazine.