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 29, 2011
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mostly suburban county bordering the bronx to the south and fairfield county, ct to the north. largely perceived as a haven for wealthy investment bankers, lawyers and doctors who commute to and work in manhattan, westchester does indeed have more than its fair share of elite golf courses (think winged foot), high-end stores (gucci, louis vuitton etc) and country clubs.

however, while one of the ten wealthiest counties in america, there is more to westchester than the popular public perception might suggest. herein lies a breakdown of westchester locales:

Preppy and Rich- think Rye, Bronxville and Larchmont. You'll find the old-school clubs (Larchmont Yacht, Westchester Country Club) and preppier atmospheres in these towns. Replete with pastel polos, sailboats and topsiders, these towns are among the wealthiest (if not necessarily flashiest) of the county.

Jappy and Rich- most famously Scarsdale and, to a lesser extent, Chappaqua. These towns are a bit more status-obsessed than their preppy counterparts. Their school systems are among the highest-performing in the nation and they tend to attract many Jewish and Asian families that put a premium on their children's educations. Think of designer clothes behind the wheel of a mercedes sports car as opposed to a vineyard vines polo behind the wheel of a jeeb or volvo to understand the difference between preppy and jappy wealth.

Guido Rich- Think Harrison, Pelham and parts of New Rochelle. Think gelled hair, Armani Exchange, fake tans and heavy make-up. Easy to confuse for imports from New Jersey.

Hollywood Rich- Much of the northern tier of the county, which is more rustic, appealing to celebrities seeking privacy. Bedford, North Salem, Pound Ridge and others boast several celebrity residents.

Ghetto- The last type of community one would associate with Westchester. Still, cities like Yonkers, Mount Vernon, (parts of) New Rochelle and Peekskille are far more socioeconomically and racially diverse than the rest of the county and make up a substantial portion of its population,
The classes of Westchester:

Bankers of English/Irish descent who live in Bronxville sail their boats out of Larchmont while their wives shop in Rye.

Bankers of Russian/Eastern European descent who live in Scarsdale and manage Bill Clinton's finances in Chappaqua with their Asian business partner.

"Waste Management Professionals" who live in $3 million homes and drive around Harrison in their souped-up Hummers.

Immigrant strivers in Yonkers, Mt. Vernon and Peekskille who, more often than not, tend to the lawns and house-cleaning needs of the three types mentioned above.
by Moder July 14, 2006
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The area of New York immediately north of the Bronx. Has rich areas and poorer areas. Many kids from Westchester pretend to be ghetto while their parents make 6 figure salaries. Also, people from Southern Westchester (like myself) take much offense when told we are from "upstate".
by WC Native March 1, 2006
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Bronxbuddy you do have a point. Kids at my high school literally were convinced they were "from" the Bronx because they lived there until they were like 2, and expect you to think they were tough because of that. People really do not have any idea how rich Westchester is, what we consider "Middle Class" is really more like upper middle class. Yonkers is probably the only city in Westchester co. that even remote resembles the rest of the country economically so it gets labeled a dump and ostracized by snobs in Scarsdale even though Yonkers is not poor for the most part, it is just normal middle class.
"Oh I'm not rich I'm well off" -Westchester kids who drive a BMW convertible and live in a $1 million dollar house.
by Name June 25, 2004
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a very nice, suburban country north of new york city. it contains the very rich, and moderatly poor. most of it is rich, white , preppy people who belong to a country club, and take day trips to the city with their friends.
did you see that girl with her collar popped
yeahhh shes from westchester -- so hot
by megan April 7, 2005
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A less obnoxious version of Long Island. This isn't to say that most people there aren't jerks, however.
Westchester is Bill O'Reilly and Long Island is Sean Hannity
by Mwa December 22, 2004
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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 4, 2005
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