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.
Kid 2: Westport.
Kid 1: Oh... so you must be a richie.
Kid 2: Nawmann i'm just chilling.
by apersonwholivesinwestportct December 04, 2011