Powerful Ladies Quiz: Are you Preppy?


By: Kara Duffy


Just in time for Prep History Month, August, and the release of self-identified Prep, Jenna Adamo’s Powerful Ladies Podcast, we have for you the ultimate Are You Preppy Quiz.

The term preppy comes from the subculture of people who have attended or attend university preparatory schools - usually private high schools on the east coast. Most people think of preppy based upon classic prep movies: Pretty in Pink, Scent of a Woman, School Ties, Dead Poets Society, Caddy Shack, Father of the Bride to name just a few. It used to be WASP and North East U.S. focused and that is for sure no longer the limitations. There are preps across the US and around the globe - hello, Crazy Rich Asians.

The Official Preppy Handbook is one of the best summaries and satire of the full lifestyle of a true prep. So much so that my copy, found in a random used book store, has a note inside the cover, “Happy 15th, Bitsy! Prep Wishes, Lisa “Bunny” Brubad". Pure gold.

Now let’s find out how you score in the Powerful Ladies Quiz: Are you Preppy?
For each yes answer, give yourself 1 point.

  1. Do you own anything monogramed? Add 1 point if you have multiple items monogrammed in your home. Add another point if you have everything monogrammed.

  2. Did you attend a private high school? Add 1 point if you attended a boarding school. Add another point if you were kicked out of a boarding school.

  3. Did you play any of these sports growing up: Tennis, Crew, Field Hockey, Lacrosse, Soccer, Rugby, Squash, Sailing, Horseback Riding, Fencing? Add 1 point for each sport played. Add another point for each sport you still play.

  4. Do you shop at L.L.Bean, Brooks Brothers, Lilly Pulitzer, Murray’s Toggery Shop Nantucket, Sperry Topsider, Lacoste, Tory Burch, or Vineyard Vines? Add 1 point if you own a pair of L.L.Bean boots or slippers. Add 1 point if you have owned multiple pairs of Topsiders. Add 1 point if you own anything in Nantucket Red. Add 1 point if you own anything with a repeat embroidery such as whales, anchors, lobsters, etc.

  5. Have you ever attended Etiquette School or an Etiquette Class?

  6. Do you own a boat on which you can host friends - overnight or for a sunset cruise?

  7. If you’re female, did you have short hair until 10, when you could then take care of it yourself? If male, do you own a tie in school colors?

  8. Do you own or did you grow up with home decor including ship models, nautical memorabilia, animal decor (dogs, ducks, horses, boats, or birds), lighthouses, framed historical documents, or portraits of ancestors? Add 1 point for each category.

  9. Do you have or did you have a nanny, cook, house keeper, gardener, private tutor, or butler? Add 1 point for each.

  10. Where you a Debutante or did you attend a Debutante Ball?

  11. Do you/did you go on ski vacations over Christmas break?

  12. For College did you attend: Amherst, Babson, Boston College, Bowdin, Brown, Bryn Mawr, Bucknell, Colby, Colgate, College of Charlston, Colorado College, Connecticut College, Dartmouth, Duke, Elon, Furman, Georgetown, Hampden-Sydney, Hamilton, Harvard, Hobart & William Smith, Holy Cross, Lafayette, Lake Forest, Miami University of Ohio, Middlebury, Mount Holyoke, Ole Miss, Penn, Pepperdine, Princeton, Sewanee, Smith, Southern Methodist, Sweet Briar, Trinity, University of Colorado, University of Virginia, UNC, USC, Vanderbilt, Vassar, Wheaton, Wellesley, William & Mary, Williams, Yale.

  13. Were you in a sorority or fraternity? Add an additional point if you are a member of Skull & Bones or another secret society.

  14. Did you travel the year after college or the year before?

  15. Do you avoid wearing black unless for black tie events or galas?

  16. Are a member at a golf club, sailing club, yacht club, country club, private beach club, or other members only organization that has a bar where you meet? Add 1 point for each membership.

  17. Do you go to dive bars at night and mimosa brunch in the morning?

  18. Do you love clothing with stripes? Add 1 additional point if your significant other casually suggested that maybe you buy something other than stripes.

  19. Have you visited in the US: Nantucket, MA; , Aspen, CO; Scottsdale, AZ; Charleston, SC; Mackinac Island, MI; Montauk, NY; Boston, MA; Washington, D.C., Newport Beach, CA; East Grand Rapids, MI; Savannah, GA; Raleigh, NC; Lexington, KY; San Francisco, CA; Baltimore, MD; Portland, ME; Newport, RI. Add 1 additional point for each city you’ve lived in.

  20. Do you have a trust or is there a trust in your name?

  21. Are you a member of charity?

  22. Do you keep things and repair them for as long as possible because it’s practical, you’d rather spend your money on your next trip to Europe/the Cape/Aspen/Long Island/Scotsdale/Charleston/Hong Kong/Singapore/the Caribbean/Palm Beach, things aren’t made the way they used to, and/or everything new is flashy new money - yuck?

  23. Do you listen to NPR? Add an additional point if you support your local NPR station with monthly or annual financial donations.

  24. Do you attend your alma mater’s alumni events, homecoming weekend, or tail gate at it’s sporting events? Add an additional point if you organize any of these events.

  25. Have you gotten a job because of mum or dad’s contacts?

  26. If you’re female do you own a slip and if your male do you own cufflinks?

  27. Are role models Gwyneth Paltrow, Alexa Chung, Taylor Swift, Kate Mara, Rashida Jones, Reece Witherspoon, Princess Diana, Jackie O, Grace Kelly, Blake Lively, Martha Stewart, Sarah Michelle Gellar, Kate Middleton, Sarah Jessica Parker or Joanna Gaines?

  28. Is great skin, great eyebrows, and the best natural looking lashes preferred over the current “influencer” full face makeup?

  29. Do you host dinner parties and theme parties?

  30. Have you rebelled against your families preppiness by choosing to live in a tiny house, taken up skateboarding, started a punk rock band, refused to smile at events you’ve been forced to attend or any other form of general “I’m not preppy” rebelliousness? Add 1 additional point for each version of rebellion, disowning, or other denials of your childhood you’ve adopted.

How did you score??

0-10: Preppies still exist?

10-20: Prep Tendencies

20-30: Raised Preppy

30-40: Confirmed Preppy

40+: Preppiest of them All

What did we miss in the Powerful Ladies Preppy Quiz? Do you think your score is accurate? Tell us below in the comment section.