What do you think is the most preppy city and the least preppy city .
And preppy I mean people who dress up more or the preppy look like collar shirt or polar shirt.
And least preppy the dress down casual look ( around the house ,for walk or to gym or bed) like jean shorts ,gym shorts ,Jersey shirt ,tank top , plain house t-shirt and jeans or sweatpants or tracksuit so on.
I hear New York and Boston is preppy where Portland Oregon ,Detroit and Philadelphia is very dress down casual look .
I always feel under-dressed in Italian cities. They seem to have a lot higher expectation for what should be worn when just walking around.
I imagine some cities in third-world countries have low expectations as to clothing simply because a lot of people can’t afford much in the way of clothes.
Polar shirt?
They are bunched at the top and bottom.
When I think of preppies, I think of the northeast, particularly the ritzier areas of Massachusetts and Connecticut.
Non-preppy: Austin, TX, and Portland, OR.
Usually much more appearance obsessed, or at least you are not going to see the professional set dressed in potato sacks.
New York City proper is highly snobby and can be fashion-conscious, but I never thought of it as particularly “preppy.” Many of its wealthier suburbs in Long Island, New Jersey, and Connecticut would, however, fit the bill.
Boston does have that preppy element.
I think the poster got that. The problem is it is really called a “Polo Shirt” (as one of your links shows) and “Polar Shirt” is considered a misspelling. We get very arsey about these things around here and like to point out anything anyone got wrong and/or show how superior we are.
Or, perhaps, I just genuinely didn’t know what the OP was talking about and was asking for clarification. But, nah, why not just go ahead and leap to the conclusion that I’m a massive douchebag? Much safer and easier. It must be nice to be able to discern the motivations and underlying attitudes of every comment on the internet.
Most preppy: Boston
Least preppy: Portland, OR. Hands down.
I remember reading a restaurant review in the Austin Chronicle that said something like, “Dress at this place is ‘formal,’ which of course in Austin means ‘clean shorts after 5’.” I thought that was apt.
For preppiest city I nominate Washington DC. At least downtown, the general dress style strikes me as much more conservative and buttoned-down than other major cities. There’s probably a greater density of actual prep school grads there, too. I would wager there is a greater density of men in nonironic bow ties.
DC is close, but I’d say for full-on preppiest it’s probably Annapolis Maryland. The DC preps are largely visitors, while the real population has serious style. If you see a polo shirt in a DC night club, you’re almost certainly looking at a tourist or an intern. In Annapolis, it’s hard to find anything else in the shops.
I’m not sure Lily Pulitzer even has a DC store?
Come on! Have you guys ever *been *to Florida?
So does non-preppy = hipster?
Not necessarily. In African cities I’ve been to, everyone (at least everyone relatively well-off) seems to wear a suit, or at least a smart shirt and trousers.
There’s definitely some overlap, but not completely. I don’t think of Los Angeles as preppy, but it’s not really hipster either. You’ve got to go farther north for that scene. But I can’t really think of any places that are both preppy and hipster. Are there any white-collar preppies working in Manhattan but living in Brooklyn alongside the Williamsburg hipsters?
Absolutely. Especially the north. I live in the north of Italy and I feel continuously under-dressed. When I go home to The Netherlands, people always comment on how smart I’m looking these days and I start to believe it until I get back to Italy and I feel downright scruffy.
The Dutch, I suppose are very casual. Like, the material and quality of the clothes are fairly good, but they value practicality over looks definitely. However, the most casual place I’ve lived in was a small town in rural Ireland - I was among the dressiest people in town there. 
Don’t know if it true but I hear France people really dress up there way more than the US.
I hear Southeast Asian countries they dress very casual more so than people in the US it not command to see people dress like this in public http://static.sglinks.com/assets/pages/4c/30/4c3008eaaee101eef5db4d371b915a88_330.jpg or http://radiantdreamer.net/wp/singapore/singapore06/singapore06_71.jpg or http://www.sixthseal.com/images/rhb/movie.jpg or http://www.sixthseal.com/images/kl/ebanking.jpg
I have not seen the sweatpants thing in public there like in the US and people more likely to wear shorts there.
I have not seen thug thing there the baggy pants sagging like in the US.
Most preppy: Nantucket, Rhode Island
Least preppy: Modesto, California
