All The Rules To Follow From The Iconic 'Official Preppy Handbook'

Lisa Birnbach wrote and edited the book that would quickly become a defining piece of 1980s culture, if only for the clothing people wore as a result of its popularity. Following its publication, kids in the American Midwest were wearing boat shoes. Even my father, who grew up in a working class home in California, admitted to owning a copy himself. If that’s not a symbol of how prep and the book, which is no longer in print, came in style, I don’t know what is.

So why the rapid popularity of the book and of the preppy look in general? I wasn’t even born yet when preppiness reached its height in the ‘80s, but it’s easy to understand the appeal. My mind immediately goes to Gilmore Girls. What girl hasn’t wanted Rory Gilmore’s life for a moment? Her middle class upbringing with single mom Lorelai and no nannies in sight paints her as a fish out of water joining a new world, but make no mistake, Rory was a preppy. She went to Chilton and then Yale, had a proper coming out at a debutante ball, and even had her preppy rebellion when she took a joyride on that yacht (a rite of passage, if the pages dedicated to getting thrown out of a prep school are to be believed).

But whether it’s beloved characters like Rory Gilmore and Blair Waldorf, or the popularity of the actual preppy handbook, it’s clear that there’s a desire to (at least in a fantasy world) be a part of this elite club where people vacation at summer homes in Cape Cod and own a boat (making the boat shoes Midwestern kids copied from the preps actually appropriate).  

And Birnbach, an outsider herself as a Jew from New York, plays right into that: “It’s the inalienable right of every man, woman, and child to wear khaki. Looking, acting, and ultimately being Prep is not restricted to an elite minority lucky enough to attend prestigious private schools, just because an ancestor or two arrived on the Mayflower. You don’t even have to be a Republican. In a true democracy, everyone can be upper class and live in Connecticut. It’s only fair.”

The idea that “everyone can be upper class and live in Connecticut” is so preposterous that if the average reader in the ‘80s would have read the introduction they would have quickly seen the satire and with further reading have realized that the guidebook in fact reveals that the exact opposite is the case. But even if it’s impossible, we’re going to take a deep dive into all it takes to be a preppy anyway, purely for the fun of it. (And believe me, we’re going to get specific.)

The Proper Childhood

Unfortunately for those not born preppy, Birnbach quickly reveals that being preppy is a birthright. You don’t gain citizenship later in life. And there’s a lot that goes into a properly preppy childhood, starting with your name, or nickname rather. Having a good nickname is of the utmost importance. For girls, Muffy, Missy, Buffy, Bitsy, Bootsy, Bunny, Kiki, Tiffy, Topsy, Cuffy, Corkie, and Molly are preferred. And for young lads, Skip, Chip, Kip, Trip, Bif, Bunny, Bink, Van, Win, Wog, Rocky, and Jack are the most popular.

Even at this young age, appearance matters a great deal. Girls are to have short hair until age 10, and for the boys’ part there’s even a correct type of underwear for their age group. (It’s white briefs, if you’re wondering.)

Girls are to have short hair until age 10 and must take piano and French lessons.

Boys and girls should begin piano lessons by age 10, take French lessons with a tutor (who must be referred to as maître d’ tutor and come to the house), have tennis lessons from the son of a family friend, take sailing lessons, and lastly they must attend summer camp to learn a fondness for the outdoors. Ballet and horseback riding are additional educational experiences for girls. Ballet begins when you’re itty bitty, but is later discouraged so you go to college rather than run off to join the ballet, never giving your mother any grandchildren. As for the riding lessons, those begin when the daughter sweetly asks her father at age 10 and consequently becomes annoyingly obsessed with horses, before her interest in boys distracts her. Didn’t I tell you Birnbach gets specific?

When a young girl reaches her teenage years, it’s necessary that she has a proper debutante ball, which you have to have the right lineage to be invited to. Then comes the dress (a different one for each ball), long white gloves, white shoes, and naturally a strand of pearls.

School (and Not Just Any)

Prep comes from preparatory school, so it’s a given that academics are important to gaining entrance into this gated community. But a prep can’t go to school just anywhere. What, some public schools are good, you say? Not if you want to be a preppy. Private prep schools, whether they’re boarding or day schools, are a must (though boarding is the more preppy of the two).

Just as in childhood, there are certain activities preppy high schoolers must be involved in. The students must take up soccer, tennis, skiing, squash, paddle tennis, lacrosse, or ice hockey. Field hockey is also suitable for girls, with rugby and crew being just for boys. Football, baseball, basketball? Not preppy enough. Any middle class American plays those after all.

Additionally, prep school students must take up other extracurriculars like school committees or the newspaper. After all, that’s what gets you into the right colleges.

Math and science majors make you look future focused, which is decidedly not preppy.

Once you get into the right college, preferably an Ivy League school like Harvard, Yale, or Princeton, it’s time to pick a major. The options are English, history, economics, or classics. Math and science majors make you look like you’re focused on the future, which is decidedly not the preppy look. As for the dorm room, keep that same laissez faire attitude and decorate with beer cans, random items from prep school, and your father’s oar.

So you’ve graduated? Job options. Pick from the following: lawyer, stock broker, account executive, investment banker, art dealer, rare book dealer, editor, furniture restorer, landscape gardener, college or prep school admissions officer, tennis pro, rancher, carpenter, nonprofit organization director, yacht designer, philanthropist, or the notorious ne'er do-well. But before you get going, the Grand Tour of Europe is an essential. Not to worry, mummy and daddy have it covered.

The Right Marriage

The right marriage basically means marrying another preppy. You, of course, need to have your engagement announced in The Times. Be sure to have no more than 8 or 9 bridesmaids as 10 is far too many. Flower girls and ring bearers just aren’t done. 

The dress code depends on the time of your wedding. If it’s at 4:00 or 4:30, the bridesmaids wear pastel dresses and the groomsmen wear morning coats. For a wedding at 6:00 or later, the dress code is black tie. The reception must be in a tent where old timey music is played. And if there’s not a feature on the wedding in The Times, well, that’s unfortunate.

The Preppy Home

For every preppy the time comes to buy a house. Be sure it’s in the suburbs, but remember it can’t just be any suburb. It needs a country club with eight tennis courts, a Ford or BMW dealership, a train, a respectable needlepoint shop, good soil for the herb garden, and good private schools. (Private being the key word here.)

Make sure it’s decorated to remind you of the summer house. 

As for decorating your home, make sure that it’s decorated to remind you of the summer house. French windows and walls that are painted Williamsburg green are both requirements along with about 28 other rules, the last of which being all the books you must include on the bookcase in your living room. Oh, and be sure there are duck motifs throughout.

There’s More To It Than Boat Shoes

The first thing that probably came to mind when you read “Preppy Handbook” was clothes. Don’t worry, those were also covered extensively. There are exactly 12 pairs of shoes the female preppy must own, including the brand they must be from and the appropriate colors. There’s a note on how men’s shirt monograms must always be on the left side in small block letters that are practically undetectable. And another detail about girls each owning a Calvin Klein denim skirt that must have the label taken off. If being a preppy is anything, it’s certainly precise.

Closing Thoughts

It sure is exhausting being a preppy. There are countless rules to be followed and undoubtedly even small distinctions that Birnbach, though very thorough, missed. It would be pretty impossible for someone not born into that world to pass as one of their own. But Birnbach’s book is written in jest anyway, and it's such a delightful glimpse into another world that you’ll enjoy the guidebook just for the heck of it. Warning: boat shoes may be purchased as a result of reading.

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