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DC, easily. Not sure how someone said San Francisco. Sure, even cities like San Francisco, Seattle, and Portland have preppy suburbs and neighborhoods, but not sure how anyone could define these cities as "preppy".
DC more preppy than SF and Seattle??? yeah right.... you've obviously never been to DC before.
Most of the east coast for that matter but DEFINITELY Charleston, DC, NYC, BOS. Not so much LA. If you wear a piece of Ralph Lauren out here you are regarded as either being a prep or have class.
LA is probably the least preppy city in the country and seems to pride itself on that. SF is a bit more preppy as it has more of an "old money" component and a huge financial sector + supporting industries (plus a huge concentration of Ivy grads) - but it feels like a clash compared to the stereotype of the rest of the city. Neither is as wholly preppy as most E Coast cities, however, as opposed to an E Coast city/Southern city where *everyone* is preppy, in SF if you see someone who is preppy (all in one area of town), you can automatically draw conclusions. The preppy set in SF is generally very upper echelon and feels more Taft/Choate than "good public school".
I thought you were crazy for saying SF is preppy earlier in the thread but then I thought about it outside of my own social circle. I remembered all the transplants in the Marina, on Union and Lombard streets, etc that at a glance / brief interaction I would classify as preppy (or douchebags ). Then I remembered I went to an actual 'prep' high school (Sacred Heart Cathedral Preparatory) looool. But still, I would not call the clientele of my HS preppy, despite having a polo shirt and khakis dress code. But there was a school within my crowd that was preppy, St. Ignatius [College Preparatory]. The difference between the two schools wasn't so much the SF natives, but the different parts of the inner Bay Area that each school attracted. While my school attracted those from the East Bay and slightly less affluent parts of the Peninsula, St. Ignatius was a hub for Marin County and the more affluent parts of the Peninsula. Two other preppy Catholic high schools in the city are Stuart Hall (also has a K-8) which is an all boys school & Convent [of the Sacred Heart] which is an all girls school. There are also a few preppy non Catholic private high schools: University, Urban & Lick-Wilmerding to an extent.
Western Suburbs of Boston absolutely. The city of Boston no, not even close.
That's my feeling, too. Boston is much more culturally diverse than many people realize.
The Philadelphia and NYC areas are very similar--a very large, preppy "old money" influence in the suburbs, but the cities themselves have a very large diversity of backgrounds and cultures such that no stereotype can possibly apply.
Honestly, I'd nominate DC as the most stereotypically preppy city on the East Coast. It has an extremely conservative vibe -- in dress, social culture and behavior -- in modern times that surpasses any other city I've ever seen.
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