A suburban area in NY that everybody from the Bronx moves to.
by Anonymous October 1, 2003
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Westchester is upstate according to New York City. High school kids drive Mercedez, Bmw's, range rovers, etc... to school. There really is no ghetto except for some parts of Westchester, such as Yonkers, White Plains, Peekskill and others. They aren't that bad, but will definitely freak the residents of Rye, Scarsdale, Somers, Bedford.
The county is filled with yuppies, japs, wasps, anything you can think of. Every town thinks that they are better then the next. Competition and Gossip is what makes their worlds go round. Looking good is a must, you have to wear the latest fashion and look ultra sexy in it. The Westchester Mall located in White Plains is a main stop for any Westchesterite who knows what is going on. At this mall they have everything for anyone with money (my favorite mall in the entire country). Each floor basically goes by class... except for some late bloomers. The bottom floor is the richest with Tiffany, Gucci, Lilly, Tumi, and soon to come Chanel, and David Yurman. Second floor is family floor it has lots of childrens stores including Crewcuts the kid store of J. Crew... so cute. But, it also has Louis, Coach, Micheal Kors... etc... then the top floor is for the people that wished they have money.. .minus J. Crew which should be on the second floor.
Northern Westchester wishes they live in Rye and Scarsdale but wont admit it. Somers is extremely wealthy home to many CEO's of Pepsi, IBM etc. Nobody knows this town because there is absolutely nothing in it except for a gated community filled with old people who wont let anything happen without their approval. They just got a CVS that took forever to get the "O.K.".
White Plains is supposedly the new Manhattan, with Trump building gorgeous multi-million dollar apartment buildings, and a Ritz Carlton just opening in the heart of the city. This city is up and coming, it really isn't touristy yet but it will be soon, night life is great and mostly located on Mamaroneck Ave. which yes, does lead in to Mamaroneck.
Orange County, our neighbor wishes they lived in Westchester, and tries desperately to be like us but doesn't pull it off. Wish they were apart of our country clubs but no, not going to happen.
Westchester Country Club one of the oldest and elites of the country clubs, has two locations the main in Rye and the beach club which is really nice. Everyone wearing Lilly, Ralph and my personal fav Vineyard Vines. Westchester is home to many prep schools that molds the children of Westchester in to their parents. "Not doing anything wrong" or at least they dont get caught. Drinking (underage) in their parents' houses or on the local golf course. Always wearing your topsiders, popped collar, and pearls while you chug one is the way to show your "molding".
There are the guidos too which take up most of lower Westchester. Yonkers, White Plains, Harrison have many of them. Most people don't know this term but guido is a guy who has a blow-out hairstyle, extremely tan and looks like he is on roids. A guidette is a girl version but instead of being insanely muscular you are just coked-out skinny. Oh yea, and they all wear Armani and go to Pacha in NYC on the weekends.
Mahopac is a wannabe Westchesterite, but you know when your in Mahopac and it is no Westchester. Extremely trashy.
Westchester is...
"What are you doing today?"
"Driving my porsche and bringing my kid to the club to meet her future husband... plastic surgeons are in"
"No way, Susan! That's exactly what I'm doing"
"I no isn't it great find them a husband and get botox injections for free... so excited!"
Both laugh.
by socialite March 18, 2008
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The county directly north of NYC bordering the Bronx. Westchester only seems as rich as it is because of the half of the towns/villages including Bronxville, Chappaqua, Scarsdale, Rye, Bedford, etc. The other half are mainly middle class but can't help but feel poor when they are always being compared to the places listed above when in fact as someone pointed out these towns would seem wealthy to the rest of the country but in the New York Metro area they are very middle class since the cost of living is so high that everything including income is higher in this area. It is a great place to live because there are many diverse places in WC, like Yonkers, White Plains etc. btw most of Yonkers is very middle class and liveable save the southwest corner which is very much so a ghetto. Also Eastchester is not "super rich" as stated above the median income there is lower than other towns considered "middle class" Hastings, Pleasantville, etc.
I was raised middle class but I felt poor in the town I lived in in upper Westchester.
by moconahhh August 5, 2013
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No, this isn't the Westchester that your thinking of in New York. This is Westchester, Illinois. A small western suburb just 15 miles from the city of Chicago.
Here you have your mostly middle and upper middle class families.
Half the kids in the town think that they are ghetto, while the other half wish they were rich and hang out with Hinsdale, Western Springs, & Burr Ridge kids all the time.

If your a Westchester kid and you play baseball or softball, well then you know about 80% of the families in town.
A majority of the kids in Westchester end up going to the following high schools: St. Joes, Proviso West, PMSA, Montini. And then the preppier kids head on over to Naz.
In Westchester, every night is a party.

One of the most exciting things that happens in Westchester is THE FEST. This is the one event that every person in this town lives for. It happens only one weekend a year and occurs in July. The fest is a place where you can get food and slushies, listen to awful live bands, ride rides. Most importantly its a place where everyone is wasted and its perfectly normal.
OMG only 105 days till Westchester Fest!

Westchester always has parties
by Westchester Local March 7, 2011
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You know you've never been out of Westchester when:

a) you refer to White Plains and New Rochelle as 'ghetto'
b) that one time in your whole life when you went to Brooklyn (likely gentrified Brooklyn Heights, no less) you actually expected to hear people talking in Brooklyn accents.
c) You group all neighborhoods in the Bronx and Brooklyn together as "the ghetto", even areas that are predominantly white, low-crime, and working class (Bensonhurst, Kingsbridge, Throgs Neck, etc); that is, your definition of ghetto is anything poorer than Westchester.
d) you believe the subway is a lot faster than it actually is. People in remote parts of Brooklyn like Sheepshead Bay or Gravesend don't get to Manhattan any faster than the Metro-North train from lower Westchester.

Note that not everyone in Westchester is a suburban hermit, i live there and have been to just about every corner of the 4 main boroughs. But soooo many people fit this description, it's really sad, White Plains is NOT ghetto, not even remotely. And New Rochelle is like Sesame Street compared to the worst parts of Brooklyn. So you don't live inthe ghetto westchester people, get over it.
I was a suburban hermit until about a year ago.
by Fuckahoe Tuckahoe March 5, 2005
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A group of parasites feeding off of the wealth and prosperity that rightly belongs to New York City. Would certainly not exist without the five boroughs directly south of it. If you happen to be in the east side of Manhattan, keep an eye out for a tall person wearing Vineyard Vines sporting a briefcase.

Be especially careful when near Metro-North train stations. If you happen to be near a train station, read the timetables so you can stay safe when a train approaches and Westchester residents get off.

Worst case scenario, if you ever find yourself in Westchester try and be along the Harlem Metro North Line. People who reside in places such as Bronxville, Scarsdale and White Plains tend to be more tolerable than people who reside in places like New Rochelle, Larchmont and Rye.

If you happen to be in the North part of Westchester county, try and take a train further north as that could be your best escape route. Try and get to a New Haven Line train and take a train to Connecticut which is the quickest way to escape. If this option is unavailable, take a train to Brewster or Manitou which are in Putnam county and therefore much safer.

For your own safety, please do not take any peak-direction trains during rush hour. This includes trains going in to the city in the morning and out of the city in the evening. These trains are full of pests who are slowly feeding on New York City and you should never be around them.
Westchester is a terrible terrible place. Perhaps I would rather reside in Hell.
by Esteban Q. April 5, 2017
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the most arrogant rich obnoxious county in new york. full of WASPs who act politically correct against their will and make $200,000+ a year.
I hate living in westchester life sucks to be rich because no one understands my problems.
by wordmasta42 June 23, 2005
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