Most misunderstood county in New York, subject of many stereotypes.
There's a lot more to WC than rich kids and IBM.
People automatically assume things when you tell them you're from Westchester.

Yes, I'm of Eastern European descent. No, I'm not related to organized crime.
Yes, I am prescribed Prozac. No, I'm not addicted to prescription pills.
Yes, my family is "comfortable". No, we're not insanely "rich".
Yes, I enjoy nice things. No, I'm not a snob.

I drive a Volvo, not an Escalade.
I enjoy the cultural aspects of Westchester, I am not obsessed with popping my collar, my diamond encrusted iPhone, or my Beamer.

And I am not a "rich kid pretending to be poor" or "ghetto".
I never claim to be "hood" or "under privileged", I wear Versace AND clothes from Goodwill, because I like it all.
It's a WC thing.
-"Where are you from?"
-"Westchester."
-"Oh, that explains it."
by JoeySeven77 May 09, 2011
A city in Illinois. Middle class for the most part.
-Hey where do you live?
-Westchester
-In NY?
-No, in Illinois. It's 30 min from chicago and is near oakbrook -and lagrange.
-ooh.

No one knows about westchester,IL
by c-unitt July 31, 2009
A very clique-y county north of New York City, and whoever lives there, regardless if their small town is in fact an hour away, "live just outside the city." Westchester is divided strictly into two parts. Basically, the ultra-rich part, and the normal part. This division comes into affect around Bronxville...this is NOT the Bronx. ("ew, the bronx, are you eff-ing kidding me? I live in bronxVILLE.")
You know you live in Westchester when you refer to white plains as "so ghetto.", and no matter what, you belong to at least two shore clubs, not country clubs, and scoff at the thought of actually stepping into "the sound. ew." Also, you know it's a major risk going to the galleria, after all, you could get shot. The Westchester is the place to be, holler.
by katie March 03, 2005
A slightly confusing insult hurled at people who might not quite be from the 'hood. Probably not used outside of New York City, much.
Person from the 'hood: Whatever, WESTCHESTER!

Person not from the 'hood: What? I'm not from Westchester, I'm from Ohio.

Person from the 'hood: Yeah, you definitely WESTCHESTER!

Person not from the 'hood: Ummm... okay... thanks?
by nyc14gauge September 22, 2009
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 05, 2013
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
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