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Lots of suburbs around Boston seem to fit, although most of them aren't cities. Wellesley. Sherborn, Natick, Dover, Medfield, Holliston, Newton, Needham, Weston, Hingham, Cohasset, and a few others are preppy. On Cape Cod, I would say that the most preppy town is Chatham.
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Originally Posted by rubber_factory
Charleston and D.C. are like Mecca and Medina for preppy kids in the Carolinas.
Big time...other 'mega-preppy' towns in the South:
Highlands, NC
Cashiers, NC
Aiken, SC
Hilton Head Island, SC
Bluffton, SC
St Simons Island, GA
Sea Island, GA
Ponte Vedra Beach, FL
Mountain Brook, AL
Fairhope, AL
Grayton Beach, FL
Seaside, FL
Palm Beach, FL
Hobe Sound, FL
Oxford, MS
Bellemeade, TN
Just look for any community that has Orvis, Ann Taylor, Talbot's and Lilly Pulitzer stores and you'll find preppy.
I know the term traditionally applies to towns in the northeast such as Nantucket.
All cities will have different kinds of people. But try to rank the following cities according to their preppyness:
Seattle
Portland
San Francisco
San Diego
Denver
Austin
Dallas
Chicago
New York City
Boston
Add other major cities if you like.
Of the cities listed, Boston, San Francisco, NYC, and Chicago are the most preppy because they have the most historic old-money neighborhoods, institutions, schools, and cultures.
Dallas is in the next rung down--it has historic old-money neighborhoods and enclaves, preppy schools and other institutions, but the city is not as historic as the above cities, and the preppy islands are surrounded by lots of nouveaux riches.
Denver is in the next rung down--it has a couple of historic old-money neighborhoods, and there is some preppy or old-money culture, but the schools and other institutions are not traditional preppy bastions.
San Diego may be on the same rung as Denver, maybe a step down--there are some preppy communities, but relatively little old money, and no historic prep school or private university of preppy status.
Seattle, Portland, and Austin are very upscale and have wealthy communities, but they are not really old money and preppy. In some ways, they are anti-preppy and anti-Eastern Establishment. The old money preppies tend to look toward traditional industries such as banking and finance; Seattle, Portland, and Austin look more toward modern industries such as high tech.
Chatham, MA but only between Memorial Day and Labour Day.
Cape Locals? noooooo. You're cape house has to be your second house.
dem has a good list of suburbs of Boston but some fit better than others. Newton? The kids are too urban and jewish- most of them end up too artsy to be preppy. I don't really see Natick, Holliston, or Medfield making the cut. But overall, an outstanding list. Dover, Sherborn, Weston especially. On the north shore you got Manchester-by-the-sea, part of Beverely, and maybe Hamilton and Wenham. Lexington, Belmont, and my home town of Winchester could be on there too along with Wayland, Concord, Carslile, etc. But really, anywhere in the Boston area has some preppy elements and it isn't nessecarily purely based on wealth.
Seems like it's big in some communities of the south too as others have said. And of course, Fairfield County, Connecticut.
summers in Newport Rhode Island, can't get any more preppier than that. everybody looks like they fell out of calvin klein or ralph lauren or jcrew. after spending the day yachting or playing polo - and not the water version.
they also invented the newport shorts. basically khaki's in crazy bold colors with belts that have whales on them.
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