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8.
Westport is a fairly wealthy town in Fairfield County Connecticut, but not everybody is filthy rich. The majority of people are upper middle class- not multimillionaires like the other definitions seem to suggest. It is a nice town, even with many extremely stuck up people. In the high school, there is a big drinking problem. And yes, many of our parent's have gone to Ivy Leagues, but we are expected to go to a nice college that is the right fit for us. While the kids here tend to wear nice clothes, many kids shop at cheap store like Forever 21 . The kids can be pretty stuck up but if you find the right group of people to chill with, you're fine.
Kid 1: So where do you live?
Kid 2: Westport.
Kid 1: Oh... so you must be a richie.
Kid 2: Nawmann i'm just chilling.
by apersonwholivesinwestportct December 04, 2011
25 6
 
9.
Rich ass town, where students get high and drunk on a frequent basis because there's nothing to fucking DO!!! Also there are a lot of parties take place here. (although becoming less frequent)
Westport: where partying, getting high and getting drunk reign supreme.
by wepo October 18, 2007
50 34
 
10.
I am extremely offended by what people have said about our town. Most of it isn't even true. First of all, not everyone gets drunk all the time and smokes pot. Though there may be a lot of people who do, what makes that so different from every other suburban town in America? Second of all, the people who have 2 multimillion dollar homes, boats, yacht clubs, etc...there arent too many of them. Third, not everyone is a complete jackass and extremely materialistic. Plenty of people in this town are people who made their own money and most people I know I happen to like. Last: the Jew comment. Westport is 35% Jewish. I find it extremely offensive to call this place jewville because A) it's not true and B) its discriminatory. So, is Westport perfect? No. But people need to give it more credit.
P.S. Why is Westport on Urbandictionary.com anyways?
by its ok June 20, 2005
148 134
 
11.
I can honestly say that Westport is a really rich town and lots of people wear really nice clothes get good grades and cool cars but most of the people are good people. Is there a problem with having fun with your money and buying a boat or a car as long as you earn it ... no. I have lived in Westport for 13 years and i don't really have any complaints. To sum up Westport in a few words is that we have a great school system, sports programs, big houses, and a beautiful town. You'll have a good time if you find the right people for you and don't let others influence you. Every town has their problems and Westport's happens to be drinking. I guess we do think of Norwalk as "ghettos" but thats only because Westport is a really safe community and were not use to being in a city or a poorer community. People who dont live in Westport and are getting these signals that we are rich snobs we have all had our hard times so please just look at it like a different life style then yours or any other town.
Ps. If you come to Westport you wont be let down
by Julliette O August 24, 2011
16 5
 
12.
i live in westport and i have all my life. everybody here is extremly rich and most people are stuck up snobs. if you dont have an expensive car and amazing clothes you can just forget about having respected friends. there are a lot of drugs and parties in westport but somehow 98% of westport kids go to collage and most land up at ive league schools. westport grades are different from most other places, in westport a b+ is really an a almost anywhere else. everybody here is extremly racist and for the most part dont car about other people. the biggest thing to girls in westport are making sure that there designer things get noticed by people.
welcome to westport the town full of backstabing bitches
by xo rich bitch November 07, 2006
27 20
 
13.
Some definitions make it seem like snobs who sit on our ass all day and drive fancy cars...We work hard for the money we have...not only do we have amazing athletics in Staples (Westport HS) kids here party four nights a week...Go to Yale after HS...get a six figure job...move back to westport...I love it here
Westporter 1: Should I take the benz or the W?
Westporter 2:If were drinking take the benz, we can afford to scuff it up...
by Livinwestportandlovinit June 19, 2005
58 55
 
14.
A very rich town. A place that has huge mansions luxury cars lining the streets and celebrity residents that just seem to blend in. The kids in the town are oblivious to the real world. There are two high schools in the town Greens Farms Academy (for the very rich kids) and the public Staples High School (for the run of the mill rich kids). Staples has a stick so far up its academic ass it can't even bend over. A Westport night for kids consists of getting drunk or stoned going to a house party the cops showing up then everyone goes down to the beach. Basically, the town is uptight and I would advise not moving here if you don’t like to compete with everyone else.
Welcome to Staples High School. MAKE SURE YOU GO TO AN IVY LEAGUE SCHOOL LIKE YOUR PARENTS DID!
by shs student June 08, 2005
55 52