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Westchester 

A far superior version of Long Island.
Westchester by Anonymous July 29, 2003

westchester 

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.
westchester by Moder July 13, 2006

Westchester 

Westchester, Alabama.

The place mushroom boys go to fuck their sisters.
Benito: She's hot.
Bobby: Bro, that's your sister.
Benito: Anything goes in Westchester...

Westchester 

The county north of New York City, sometimes referred to as the "East Coast OC", this county boasts a strong history, culture, and an absurd amount of wealth. The southern half of the county is more suburban, while the northern half, while more rural, is certainly as affluent, and cannot be discounted. Yonkers is the largest city in the county, and is currently making a huge economical comeback, though it is still plagued by issues with the school district. Westchester is home to many celebrities and some of the best public schools in the country. Whether one hails from Scarsdale or Somers, they are Westchester-ites---and ultimately, Westchester is one of the most intriguing parts of the state and country to look at from a sociological and cultural standpoint.

Home of DMX, Mary J. Blige, the Clintons, Mike Myers, Richard Gere, Rob Thomas, the Reeves, Vanessa Williams, Susan Sarandon and Tim Robbins, among others.

Ella Fitzgerald was born in Yonkers, and a statue of her still stands in her old neighborhood. Matt Dillon grew up in New Rochelle and Mamoroneck. Dave Matthews briefly lived in Yorktown and attended YHS. The Son of Sam hailed from Yonkers, and Mariah Carey's house burned down in Westchester. Martha Stewart was confined to her home after prison in Bedford, and Calvin Klein owns a thoroughbred breeding farm in Somers.

Mahopac is NOT Westchester, and you can tell as soon as you step foot across the county line.
westchester is the best chester!
Westchester by tipsymcstagger September 3, 2008

Westchesterite 

A resident of Westchester, but not any citizen of Westchester, a dweller who lives in Westchester, eats in Westchester, doesn't leave Westchester, raises a family in Westchester, goes to the Lake Isle pool in Westchester, sends their kids to expensive private schools in Westchester, goes to bars in Westchester, first girlfriend/boyfriend is from Westchester, they live in a town that ends with Dale, Ville or Chester, their house takes up a city block in Westchester, they call a sandwich a wedge but only in Westchester, if its not kosher approved the business doesn't last in Westchester, if you lawn is not green and properly trimmed your not from Westchester, If you are not wearing a name brand you will be assumed to have moved into Westchester, they only eat organic foods in Westchester, the streets are always paved smooth in Westchester, and finally you will live and die in Westchester.
If you are reading this you are probably a Westchesterite.
Westchesterite by Danny Hunnewell January 14, 2008

Westchester 

Westchester, New York (aka Alabama)

The place where mushroom boys go to fuck their sisters.
Benito: She's hot.
Bobby: Bro, that's your sister.
Benito: Anything goes in Westchester...
More from Urban Dictionary

Oblication 

A vacation, feeling more like an obligation, that involves visiting or staying with family.
So Joe where are you taking the kids for spring break vacation? We are going on an oblication to Boca to visit my mother-in-law.
Oblication by kimmerr May 5, 2011
Word of the Day on October 25, 2026

Surf Dracula Syndrome 

A phenomenon in film/television series, most notably streaming series, where the main premise is drawn out to such a point that it takes an entire season or more to get the parts of the series the audience is actually interested in seeing.

For example, if a series is titled "Surf Dracula," a majority of viewers would tune in expecting to see Dracula surfing by the first or second episode. However, the entire first season would instead be tedious padding and backstory before finally ending with Dracula surfing in the last five minutes of the season finale.
I watched "Smallville" on Netflix the other day. Dude, it was ten seasons of filler before he finally flew! Major Surf Dracula Syndrome!
Word of the Day on October 24, 2026

Northstarring

Finding your way back to the truth by fixing on one verified fact and working out from there, the way you navigate by the North Star when everything around you is spinning.
Rumours were flying everywhere, so she went northstarring — one checked fact at a time.
Northstarring by Light Bearer October 22, 2026
Word of the Day on October 23, 2026

Plate of Brown 

A plate of brown consists of foods that have little to no nutritional value, and are typically deep fried. A true plate of brown will also be accompanied by a dark soda.
Wanna go to meal hall & grab a plate of brown?
Plate of Brown by Cheddar Craigson September 18, 2020
Word of the Day on October 22, 2026

Larpenomics

When finance content creators rent out fancy cars and flex cash to seem richer than they really are in order to promote and sell their “get rich quick” courses.
Andrew Tate has mastered the field of larpenomics
Larpenomics by Rbois09 October 21, 2026
Word of the Day on October 21, 2026

Palmela Handerson 

Your hand that you masturbate with.
Girlfriend: What are you going to do for the next week while I'm on holiday?

Boyfriend: Have a visit from Palmela Handerson of course!
Word of the Day on October 20, 2026
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