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22.
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 17, 2008
 
23.
welcome to westchester.
it's a place where collars have no sense of gravity & pink is referred to as "nantucket red." it's a place where starbucks is a regular stop & NYU is the top choice for college. it's a place where the students at school drive nicer cars than the teachers & everyone winds up spending spring break in cape cod or the bahamas. it's a place where everyone belongs to a health club, beach club, golf club, or yacht club & they call it "the club." it's a place where people take longer to do their hair than their homework. it's a place when juicy couture sweat suits are considered "casual" & you wear more make-up than the models in the magazines. it's a place where tiffany's just can't restock fast enough. it's a place where weekly pedi/manis are a must. it's a place where saving money is a foreign concept, although you have a full bank account. It's a place where every teenage girl has a credit card and spend their daddy's money. It's a place where every has a BMW or range rover and get a new car every year. its' a place where the weak won't survive. <3
i'm a westchester girl!
by cew April 01, 2007
 
24.
A small western suburb of Chicago smacked in the middle of Bellwood, Broadview, Hillside and Oak Brook. It's so secluded by the other suburbs that very few people would know about it. It's very quiet and the population is mostly either old people or rich, preppy kids who attend the area's several private schools. A very small percentage of the population is actually cool. Also known as "Deadchester" to many.
So, you live near Chicago, too? Where are you from?
Westchester.
Where's THAT at?
I'm not even gonna bother explaining where...
by hydrospanner May 28, 2011
 
25.
Where Bronxites move to when too many "mulignans" come to Throgs Neck/Morris Park or when their income exceeds a certain level.
Yo, let's move ta Eas'chesta to get away from dese mulignans takin' ova da nice Italian nabahood, ah!
by YO Man January 08, 2005
 
26.
79ave to 117ave and 32st to 48st. palm trees, taken care of house, coral gables of the cubans, but once you hit bird road from 114ave to 87ave it starts down grading barely any grass in front of the houses lots of power cables over the streets lots of cars parked on the border of the roads burglar bars on some houses and gangs belive it or not the bird road boys i think they had a video on you tube. westchester has had shootings, beatings, robberies, auto thefts, and drugs but it is liveable just like the rest of miami. westchester and hialeah are where the most cubans are at.
john: hey isnt westchester in new york
bob: yes but miami has one too
by henrybirdroadcoralway October 04, 2008
 
27.
Long Island without that whole civilization thing.
In a nutshell, the ominous beginnings of Upstate New York. If the English Countryside is your idea of paradise, but you don't want to go all the way, then this is the place for you.
Person #1:

Hello, I live in Scarsdale! That's in Westchester.... Are you impressed yet?

Person #2:

You do? My condolences...
It must be like living in suburban Washington. I mean, everything is colonial, and you have to commute through ghetto everyday. Again, my condolences...
by Ditafooka February 13, 2010
 
28.
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 05, 2005