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2 definitions by Moder

 
1.
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 13, 2006
 
2.
Traditionally, "bridge and tunnel" does not refer to suburbanites from Westchester and CT (who are on average wealthier than Manhattanites) but rather citizens of the outer-boroughs (Queens, Bronx, Staten Island, Bronx). The term is actually one of barely-contained racism and ethnic snobbery, most often applied to Italian "guidos" with thick accents
Bouncers look out for Bridge and Tunnel people like Guido and friends...
by Moder July 14, 2006