I grew up in Westport, Connecticut and my grandparents lived on Prospect Road in the Green’s Farms section of town, a place on Muffy’s list. You may also know this area as the home of Beachside Avenue (the Bedford family of Standard Oil), Greens Farms Academy (currently celebrating 100 years), and Turkey Hill (the former home of Martha Stewart).
Bedford SquareGreens Farms AcademyTurkey Hill
Muffy provides her own criteria for what makes a town preppy. Here are some of my favorite ways that my hometown meets these criteria:
Architecture and historic preservation
The Minuteman Statue commemorates the Battle of Compo which took place on April 25, 1777. Growing up in a historic place with beautiful buildings inspired me to pursue a Ph.D. in Humanities and to write a dissertation focused on architectural and cultural history.
Muffy Aldrich – a 12th generation New Englander – Reflects on The Way of the WASP in New England Culture and the state of Sloane and Preppy Clothes, and Answers Reader Questions. Editor, Salt Water New England blog since 2010.
I am sure most readers are already acquainted with Muffy’s blog, but I couldn’t endorse it highly enough. Ivy Style and SWNE are my two primary places of refuge for interest in this lifestyle. Perhaps SWNE even more so because it leans more into aspects of “old New England” life rather than Ivy – the latter of which I consider myself more of an admirer, not a participant (or alumnus for that matter).
Jerod Swanson’s Oxford Cloth Button Down blog is also excellent for style inspo.
It has been so long since I’ve lived in New England that I don’t know if I could even have an educated opinion on this matter. Westport certainly seems to fit the bill. However I attended my brother‘s wedding in Marblehead two summers ago and was reminded that there is still plenty of towns in the North Shore of Massachusetts are more than sufficiently preppy.
Keep up the great work, Matthew. Love what you have been doing to the site.
As I prefer hills and vegetation to coastal landscapes, I’d go with New Hampshire if I could. Not a long drive to the coast, anyway. ‘Tis the season for seafood. 🦞
Nice pic, Hardbopper. Down here in Virginia, at least around Charlottesville, Lexington and a few other spots, we have a fairly good claim on preppieness too. And currently, we even have frigid temps (7° last night) and a blanket of snow, with more on the way tonight. Not New England, perhaps, but we deserve at least an honorable mention. Cheers to all our east coast friends, north and south, on this chilly weekend and prayers for our friends in L.A.
Born and raised in NYC here, and between Columbia, the UES, our prep schools, and the Metropolitan/Knickerbocker/Union/Doubles/Harmonie/New York Yacht clubs I’d say our prep quotient is sufficient
If we’re willing broaden the vibe (extend the circle) beyond Gold Coast, to mountains and fields, there are lots of places/cultures bearing witness to the rustic/homespun aspects of the look. I don’t like sailing or golf (snooze), so no thanks to the red pants/cricket sweater stuff. When it comes to fuzzy sweaters, giant wale cords, flannel shirts, parkas and hiking boots, there are schools and neighborhoods that seize the day. NESCAC colleges (with the exception of Trinity), Sewanee, Colorado College, and Hamilton are outposts of outdoorsy ruggedness. Moleskin, chamois, hefty woolens, oil cloth — yes.
Grew up in Darien. I usually visit once a year and I’m pretty dismayed at the state of the place. Lots of development downtown , colonials being renovated (or bullldozed) and McMansions going up . It’s in no way unique to the region, as the same thing is happening in many strongholds of old wealth. Finding “real deal” places and people is becoming harder and harder .. but is therefore more rewarding.
The only thing less “preppy” than compiling a list of “preppy” towns in New England would be compiling said list and publishing it on the internet. Heck, TOPH was firmly tongue in cheek.
But times have changed, and I guess “influencers” gotta “influence”.
The Official Preppy Handbook is indeed tongue-in-cheek, but it is also very accurate. The book has a list titled “A Sampling of Suburbs” and was published in 1980, years before social media and influencers.
I seem to recall there being some sort of “flame war” between CC and Muffy many years ago. Perhaps my memory fails but I recall her attitudinal affectation being exposed and her WASPiness was debunked as ersatz at best. Hers was a bouffe opera sort of WASP.
The only thing preppy about Houston, my hometown, is that Wes Anderson filmed Rushmore at St. John’s school there.
I am sure most readers are already acquainted with Muffy’s blog, but I couldn’t endorse it highly enough. Ivy Style and SWNE are my two primary places of refuge for interest in this lifestyle. Perhaps SWNE even more so because it leans more into aspects of “old New England” life rather than Ivy – the latter of which I consider myself more of an admirer, not a participant (or alumnus for that matter).
Jerod Swanson’s Oxford Cloth Button Down blog is also excellent for style inspo.
It has been so long since I’ve lived in New England that I don’t know if I could even have an educated opinion on this matter. Westport certainly seems to fit the bill. However I attended my brother‘s wedding in Marblehead two summers ago and was reminded that there is still plenty of towns in the North Shore of Massachusetts are more than sufficiently preppy.
Keep up the great work, Matthew. Love what you have been doing to the site.
Thanks, Agent Ivy, for mentioning Jerod’s OCBD blog. I thought he had given it up, but see that it is back up and going strong.
*”… reminded that there ARE still plenty of towns…”
Not sure this will post.
As I prefer hills and vegetation to coastal landscapes, I’d go with New Hampshire if I could. Not a long drive to the coast, anyway. ‘Tis the season for seafood. 🦞
https://www.gettyimages.com/detail/photo/country-road-during-autumn-in-shelburne-new-royalty-free-image/1180867739
Nice pic, Hardbopper. Down here in Virginia, at least around Charlottesville, Lexington and a few other spots, we have a fairly good claim on preppieness too. And currently, we even have frigid temps (7° last night) and a blanket of snow, with more on the way tonight. Not New England, perhaps, but we deserve at least an honorable mention. Cheers to all our east coast friends, north and south, on this chilly weekend and prayers for our friends in L.A.
Born and raised in NYC here, and between Columbia, the UES, our prep schools, and the Metropolitan/Knickerbocker/Union/Doubles/Harmonie/New York Yacht clubs I’d say our prep quotient is sufficient
NYC is the preppiest place on earth. It is not, however, in New England.
Preppy New Netherland.
Neither my hometown nor where I now reside are preppy. An Italian in Algiers? An American in Paris?
I didn’t say it was
If we’re willing broaden the vibe (extend the circle) beyond Gold Coast, to mountains and fields, there are lots of places/cultures bearing witness to the rustic/homespun aspects of the look. I don’t like sailing or golf (snooze), so no thanks to the red pants/cricket sweater stuff. When it comes to fuzzy sweaters, giant wale cords, flannel shirts, parkas and hiking boots, there are schools and neighborhoods that seize the day. NESCAC colleges (with the exception of Trinity), Sewanee, Colorado College, and Hamilton are outposts of outdoorsy ruggedness. Moleskin, chamois, hefty woolens, oil cloth — yes.
Hamilton IS a NESCAC college, S.E.
Grew up in Darien. I usually visit once a year and I’m pretty dismayed at the state of the place. Lots of development downtown , colonials being renovated (or bullldozed) and McMansions going up . It’s in no way unique to the region, as the same thing is happening in many strongholds of old wealth. Finding “real deal” places and people is becoming harder and harder .. but is therefore more rewarding.
The only thing less “preppy” than compiling a list of “preppy” towns in New England would be compiling said list and publishing it on the internet. Heck, TOPH was firmly tongue in cheek.
But times have changed, and I guess “influencers” gotta “influence”.
The Official Preppy Handbook is indeed tongue-in-cheek, but it is also very accurate. The book has a list titled “A Sampling of Suburbs” and was published in 1980, years before social media and influencers.
I seem to recall there being some sort of “flame war” between CC and Muffy many years ago. Perhaps my memory fails but I recall her attitudinal affectation being exposed and her WASPiness was debunked as ersatz at best. Hers was a bouffe opera sort of WASP.
Muffy and I have a friendly rapport and I love her content. Her credentials as a WASP are firmly in place and she understands the aesthetic very well.