Producer’s note: Someone on Quora asked: Which state is the preppiest of them all? Here is one of the best answers that’s been pulled from the thread. Thank you to the team at Quora for making this happen!
To get right to the point, the preppiest state in the US is Connecticut.
Honorable Mentions: Massachusetts, Rhode Island.
I think Maine, New Hampshire and Vermont are each too rural to be the preppiest state in America. Not enough town. Too much country.
The preppiest state in America?
The preppiest state in America (confirmed by an ex-Racliffe NYC alumni club president) is Connecticut, home of Litchfield, Choate, Hotchkiss, New Canaan, Darien, Groton, New London, Old Lyme, Essex, Fairfield, J. Press, Yale, polo matches at the Greenwich Country Club, and the Stepford wives.
If we were just talking about the part of Connecticut within, say, a 2.5 hour drive of the Yale Club in midtown Manhattan, Connecticut would win in a landslide.
But alas, this was a bit closer in reality than one might think because Connecticut has New Haven (not counting the Yalie parts), Hartford, etc. Also, Stamford is not very preppy. I’d argue Yale is preppier than Harvard.
Massachusetts, home of Philips Academy, Deerfield, Harvard, Cambridge, Nantucket, Amherst, Williams College, Martha’s Vineyard, Cape Cod, Boston, Beacon Hill, Bunker Hill, Eliot House, Andover Shop, Wellesley, Boston Brahmins and the Head of the Charles. However, as Phil Darnowsky points out, Massachusetts is also the home of Southie, Lowell, Everett, Chelsea, and Lynn.
Crew is quite preppy indeed. The Head of the Charles is when preppies get down and party. Got Regatta?
Rhode Island also deserves an honorable mention. Home of yachts, Newport and Brown.
Providence and just being too far from Fairfield and Beacon Hill dilute Rhode Island’s preppiness.
Modest-sized sailboats in Newport without loud and garish “designs” on the sails are preppy. So is a lawn overlooking sailboats in Newport with white chairs that look like this.
Polo is borderline preppy. I took a lot of teasing inviting my friends to the Greenwich Country Club for polo matches. Anyone can go in the non-VIP section. It was $20 a car, so the more folks I could jam into a car the cheaper for me. Anyway, during one match an Argentinian polo player fell off his horse. People expressed concern. But they seemed more concerned for the horse. A bit disturbing if I may say so.
And I’d like to see data on the amount of revenue Brooks Brothers garners per capita, broken down by state. But just for the color lime green. Brooks is a bit mainstream these days.