Pink, Green, and Jewish: My So-Called Preppy Life

What does it mean to be preppy in today’s world? According to True Prep author Lisa Birnbach, it’s about knowing your tartan from your tweed, writing thank-you notes on engraved stationery, and using “weekend” as a gerund. DON’Ts range from texting at the table to wearing sweat pants. Ever. These and other proclamations from the new prep manifesto might seem old-school, though they are directed at a wider group of adherents—dwellers of the tony black resorts in Oak Bluffs and Sag Harbor, gays and “presbians,” the nouveau dot-com riche. Thirty years after the publication of her Official Preppy Handbook, Birnbach encourages preppies of all persuasions to kick off their Wellies and come on in to the family mudroom. That’s about as down-and-dirty as the truth gets: That everyone is welcome now. But what about then?

I grew up in one of the preppiest towns in the country. Andover, Massachusetts is home to Phillips Academy, an elite boarding school with a roster of distinguished alumni too long to list, though many Americans know it to include the Senior and Junior Presidents Bush and—if they happened to be grade-school girls during the late seventies—John F. Kennedy, Junior. Andover is not unlike many New England suburbs with its lush landscapes; historic gated mansions; plywood picket-fenced McMansions; and mostly white Anglo-Saxon Protestant residents. My Jewish parents moved us to Andover (from the New York Tri-State area) hoping to provide my brother and me with a safe environment and a solid education. Our family turned out to be a lot less stable—divorce, financial hardship, the usual—but Andover remained.

I was lucky.

And so I had the privilege of being dissatisfied. After all, my life just didn’t have the appearance of everybody else’s—at home and, more important to me at the time, in the mirror—and I desperately wanted to find a way to fit in. The Official Preppy Handbook showed me how.

But I was too young to understand that Birnbach’s prescription for preppiness wasn’t to be taken literally. Andover was a literal representation of the world Birnbach described. To be preppy was “normal.” To be, and look, Jewish? Definitely a DON’T.

So what if I’d known that Birnbach—whose chapter “Prep Hair for Women” informed:

The basic color is blond. There are some brunette preppies. Curly hair is rare—frizzy hair, unthinkable…

—was herself a dark-haired New York Jew? Or that this white-bread recipe for America was owed in large part to another Jew: Ralph Lauren (né Lifshitz), logo-bearer to the legions of polo-players in the country (whose clubs seldom welcomed Jews as members)? Would I have done things differently? All I know is what I felt then: Shame. So I did what any other self-loathing Jewish adolescent would do: Everything possible to become something, and someone, I was not.

Top on my to-change list was my unthinkably frizzy hair, which I tried to feather, iron, and layer—with disastrous results. Wardrobe purchases included pastel-colored Polos and Izods, argyle socks, penny loafers, Bermuda bags. These items are, of course, emblematic of the Eighties; I was no pioneer in my aesthetic pursuits. I was, however, a girl with dangerous curves beneath my brow and waistline. These characteristics, plus the hair, yielded considerable torment from my peers who saw in me what I couldn’t: That the harder I tried to look preppy, the more transparently Jewish I was.

Still, I invited these goyim to attend my bat mitzvah. I may never forget being up at the bima, marveling over the incongruity of my classmates—some with silky hair in ribbon barrettes, others capped in sateen yarmulkes—sitting among my family members in the pews. I suppose part of me was proud to have garnered such a guest list; some of the most popular students at my junior high showed up at Temple Emanuel to honor the occasion. Clearly, they had accepted me for who I was. And now that this whole bat-mitzvah business was over with, I could officially join their leagues.

For me, having a bat mitzvah at the age of thirteen marked the end—not the beginning, as the ritual is intended—of a lifetime devoted to Judaism. Like playing the French Horn or making papier-mâché ponies, I associated religious practice with activities performed in youth. Once you learned how to read and write in Hebrew, and recite prayers for the bread and wine, you were ready to graduate and become a real, grown-up Jew. L’Chaim!

My parents, like others of their generation, took the same crash-course. Whether they were children of Holocaust survivors (like my father) or turn-of-the-century immigrants (like my mother), they embraced Moses Mendelssohn’s age-old adage of assimilatory compromise: Be a man on the street and a Jew in your tent. Change your name and create a schmatte empire for WASPs. Or better yet, try to pass as one yourself.

As it turned out, I failed to fool anyone. Many of the guests at my bat-mitzvah after-party took to vandalizing the bathroom lounge with adolescent anti-Semitic graffiti—JAP! UGLY JAP!—and ripping open my gifts, mostly cards containing cash (which they pocketed).

As far as childhood tragedies go, again, I was lucky. But the episode yielded further confusion about my identity. As a persecuted Jew, I wanted to fight back; as an insecure, obviously unattractive young woman I wanted to disappear and/or die. In the end, the only thing I wanted more than to be among Andover’s in crowd was to get the hell out. I traded my pink and green espadrilles for a pair of black Doc Martens, went to public high school, went to college in New York City, and never looked back.

In recent interviews, Birnbach is asked how she became an authority on the WASP way of life. She claims that her insider-outsider status—as a Jewish girl who attended exclusive private schools—allowed her a unique perspective on prep culture. Because her coming-of-age happened to take place in a very Jewish Manhattan, she never felt the need to choose between one identity or another, as I did. Growing up in Andover, I never had the confidence, nor the creativity, to weave my two worlds together. It wasn’t until I left that I learned how.

In my career as a copywriter, for example, I have worked at two quintessentially preppy organizations: J.Crew and Martha Stewart Living Omnimedia. I may live in New York, and wear black every single day, but apparently I can still come up with colorful copy about loungewear and swimsuits, lawn furniture and high-thread-count sheets, or Christmas-themed tee-shirts—for canines. I mention my ability to “speak” to the preppy class not to boast but to further illustrate just how thoroughly I tried, back then, to walk the walk. Unwittingly, I found a way to talk the talk instead.

Oh, and I always write thank-you notes. But I think this has less to do with preppiness than having been raised as a nice Jewish girl. Which is more than fine by me.