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Ah, Westport. What to say about this little town in Fairfield County in Connecticut. A gorgeous town ridden with filthy rich people that have so much money that they have nothing better to do than to drive around in their luxury cars and spoil their children rotten. These children are living better right now than many the majority of the United States ever will. So what do they do? They buy all designer clothing, get either a Range Rover, a BMW, or a Lexus when they turn 16, get incredibly drunk and stoned at least twice a week. Go figure. On the other hand though, they mostly manage to do incredibly in academics and sports and many of the children will go to ivy league schools. Westport is probably one of the whitest areas that you will ever find. There are maybe 10 African American families in Westport at a maximum. Their idea of ghetto is Norwalk, Connecticut which is definitely no Harlem or anything of the sort. These peoples lives are spent at parties, renovating their already mic-mansion homes, playing tennis, and getting their hair re-dyed. Vacation is almost a whole different topic in and of itself. People are always going to some tropical island, Europe, a cruise, Martha's Vineyard, Nantucket, or Cape Cod. It is unavoidable. Oh yeah, and don't forget the celebrities who live there that these people often see in the supermarket, barnes and noble, or just walking around town like everyone else. The FC definitely gives the OC a run for their money. No pun intended of course.
Befriend everyone and you will be good.
by Westporter April 02, 2005
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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
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A beautiful, mid-sized town in Connecticut. It has great shopping areas and vast estates, particularly in the Greens Farms area. Some waterfront homes can cost in excess of 20 million dollars. Unlike many of the so called "wealthy" Long Island and New Jersey towns Westport and the neighboring Fairfield County towns do not feel the need to wear their wealth on their sleeves. However, everyone knows outside of Manhattan and The Hamptons, Fairfield County is the center of high priced homes and high class lifestyle in the metro-area. Westport is one of the greatest and richest towns in Fairfield County.
Forget Westport being the richest towns in Connecticut. It is one of the richest in America. It is a great place to live and a haven for Judeo-Protestant wealth.

Now bring around the Maybach!
by old timer December 21, 2005
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An area of Kansas City, Missouri, that is home to dozens of clubs, bars, venues, and restaurants. It is a very good place to go if you spend all your money on Armani shirts but you drive a 93 Nissan Sentra.
It is also a good place to find loose cocaine sluts.
Armani shirt 1: Hey Brad, let's go downto Westport tonight.
Armani Shirt 2: Right on bra! Let's take your Sentra.
by Rick Dank December 28, 2008
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Westport is:

1. a rich ass white town located in Fairfield county in Southwestern Connecticut

2. Home to many famous people including Paul Newman as well as the 2nd home to many New Yorkers

3. A town where everybody wears Lacoste, Polo, A&F, Seven, and Juicy and where the average pair of jeans costs about $200

4. a place where the kids are expected to go to a top school (duke, cornell, harvard, yale, stanford) and where all the varsity sports especially boys volleyball kick ass.

5. home to many kids who could drink a college senior under the table.

6. a place where the cheapest house on the block is about 2 mil

7. full of kids who get a bmw, mercedes, or a jeep for their 16th birthday and go to their summer "cottage" or their apartment in Europe of the summer.

8. the home to many that live for 4:20
Mike: hey man, what are you doin tomorrow

John: are you serious dude? it's 4/20

Mike: sick. does this polo shirt smell like pot?

John: damn were you smoking inside your bmw again?

Mike: yeah but its okay. my parents are too busy redecorating our macmansion to notice.

John: so your chill than. you wanna come to a kegger up at my beach house this weekend?

Mike: hells yes
by money money May 09, 2005
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Do i feel guilty that i own 2 multimillion dollar homes, carry multiple credit cards, drive a BMW, own a boat, belong to a yacht club, and get my choice of Ivies and play varsity sports even though i spend my weekends so wasted or stoned that i don't remember them? no. you can kiss my ass.
don't be mad cause my daddy fired your daddy
by Richer Than You April 26, 2005
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One of Connecticut’s richest towns. The kids here do massive amounts of drugs (weed, blow, and an occasional E pill) and party extremely harder then most other suburban communities. Despite the excessive partying these kids have seen the world three times over and are some of the most cultured and classiest individuals around. Young adults between the ages of 16-25 basically live in a drugged out haze of parties and sexual favors. Kids quietly compete with one another about who has the biggest summer home, who goes to the better college and who can amass the most materiel possessions. To speak openly about this competition is socially unacceptable and very unbecoming. The public school girls can be seen driving their Benz's, BMW's, Audi's, Volkswagen's and Land Rover's around town at all hours of the night looking for a house party or the next local bar to "chill" at. The private school girls can be seen in the back of their parents chauffeured Bentley attending amazing sweet sixteens, debutante balls, and benefit galas while the whole time being strung out on some prescription drug. Welcome to the world of Westport.
GFA girl 1: I want to go shopping this weekend and Westport's Main Street just won't do. I have shopped there the last 3 weekends.

GFA girl 2: OMG! I know! Lets see if my parents can arrange a jet for us so we can go to London and shop on Bond Street.
by gfa pride December 28, 2005
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