The Second Preppiest New England State
Home of "Cut them off and wave."
Over the years on the blog I have been asked countless times “What is the preppiest state?” Here is my countdown, from least to most.
All photos of/by Muffy Aldrich or her Father.
#2. Connecticut.
If Maine is dreamy and New Hampshire is boring, then Connecticut is cutthroat, fast paced, and socially competitive.
In other words, home.
To be slightly more specific, it is sharp-elbowed but in a refined manner. I would argue the state motto of Connecticut should be, “Cut them off and wave.”
You may be tailgated the entire drive down the Merritt Parkway at 6 in the morning (heading south), but the car doing it, and those all around you, will be some of the most expensive European cars around.
Connecticut is one of the oldest states and there are many different “feels” to it, and they can be quite different from each other. There is Fairfield County to the south, abutting New York, and its massive amounts of wealth. Hartford to the north, which was the insurance capitol of the world, and was just as exciting as that title would confer. (Fenwick, on the shoreline in Old Saybrook, was where they all summered.) Waterbury was the known as the Brass Capitol of the world and was once quite a very wealthy city. A bit of a different story today. And Litchfield County has always been bucolic, with its impeccably restored white houses, though they are mostly occupied by New Yorkers.
Connecticut is home to some of the best prep schools - Choate, Hotchkiss, Kent, Taft, Miss Porter’s, Ethel Walker, Loomis Chaffee.
And of course, the oh so dominant Yale University in New Haven, whose impact cannot be understated.
There are countless stunning town greens sprinkled throughout the state, and most always accompanied by a stunning Congregational Church.
Connecticut could be microcosmed (made up verb) as “that yacht club that had been started by a group of friends” a century ago, and became known as “the spot for business, political, and social connections”. And as is the Connecticut way, it was then was taken over by a new generation by hyper ambitious people who couldn’t care a whit about sailing. Black and white photos of the original founding friends remain on the walls, of course.
I have argued that the Preppy movement of the 1980s was a commercialization and knock-off of what I call, “The Thing Before Preppy” from a generation or two earlier.
Specifically:
For me, the origin of the style is in the 1950s, around the coast of Connecticut. A culture was codifying influenced by the wealth and access of New York; strong schools; and the culture of so many early settled New England towns with deep British roots. The clothes were often bright and casual but still substantive and well made, much of which came directly from nearby manufacturers. Towns also had shops that specialized in imported Irish woollens and tweeds.
This style was immortalized in many classic New Yorker covers that were done under the art direction of James Geraghty, who also happened to be the father of a longtime friend of ours.
And the charm of the New Yorker covers can still be seen today, in the right spots.
I should also say that I am not impartial. Connecticut is my state. With a few interruptions aside (schools, summers, a year or two here and there), I have lived my whole life on the Connecticut shoreline. I was born there. I went to day and prep schools there. My parents were born there. And their parents were born there, and so on. I was born at Yale’s hospital and have every intention of dying there.
Growing up along the shoreline, everyone spent time on or around the Thimbles, including my father as a lad.
