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Contrary to other definitions, Cheshire is in fact a well-heeled and well-to-do county in the North(ish) of England. It is where people own Range Rovers, cows and occasionally large expanses of land. Also home to many Manchester United footballers.
"Cripes! Look how flat it is and how many cows there are. We must be in Cheshire."
by Whippet May 29, 2005
Cheshire is a little area in CT which is too big to be called a town, but it's not really a county either. I'm from Cheshire, so yes I would know. We have huge sports rivalries with Southington and Hamden. About 92% of the kids smoke pot and/or drink and think they're cool. Most of the residents live in nice houses, have nice cars and are not worried about this recession. More than 55% of Cheshire is owned by the Bowman family. There are like 10 black kids, just stating the facts. Anyway the girls stay tan (not really tan, more of an orange) throughout winter and are mostly preppy. The guys are mostly preppy too; therefore there are no hot scene guys... They party a lot and have a record for the number of arrests that have been made, especially recently. The popular music in Cheshire is whatever's on the radio, and it's usually hip hop or rap. The preppy kids think its cool to be "punk" so now they are starting to wear checkered patterned shirts and converse, when they are clearly not original like the people who've been doing it for years. They are also starting to discover bands like 3OH!3, Cobra Starship, etc and claim to be fans, yet again, it's been done. The people are usually all fake except for a select few, and the mothers love to gossip with each other.
Cheshire Mother #1:so i hear johns kid got arrested for having a party last weekend?
Cheshire Mother #2: oh yes he told me all about it but keep it on the "D.L" because i wasnt supposed to say anything.
Mother #1 to Mother #3 over the phone: you'll never guess whos son got arrested!!!

Cheshire Football player #1: game against southington tonight!! whooo were gonna totally kill them!!
Cheshire Football player #2: yeah mannn n after we can set another one of their cars on fire then smoke a bogie behind the bleachers...
by tinygurl1747 October 05, 2009
Everybody thinks that our little bedplant town is pretty fucked. Well those b*tches are wrong. Sure we might have some money, but that doesn't make us complete dicks. Thanks for the bad rep. and the pathetic rumors. You guys are terrible people. Go to Hell. ;)
Cheshire has money, but we aren't stuck up snobs.
by smiles333 February 12, 2012
A pimpass billygoat that eats tapeworms and nails for breakfast. Afterwards he goes skinny-dipping and then jogs a mile to the nearest candyshop to poop on thier butterscotch and piss in thier cornflakes.
What a cute little cheshire.
by Beast Qoc April 02, 2011
To question someone to the point of pure exhaustion.
He was going to get the sale, but pulled a Cheshire and questioned him to death.
by Swansond January 10, 2014
Best county in New Hampshire! ...er, not really...
There's a lot of hicks around Winchester and Westmoreland, but over on the east side, you get a lot of wicked rich people, mainly in Dublin. Apparently there's a lot of famous people with summer homes on Dublin Lake. Mount Monadnock is at least partially in the county, and we have really pretty scenery, which attracts loads of tourists over summer. Home of the Cheshire Fair, which is actually kinda lame, and the Swamp Bats baseball team.
NH person: "I'm from Cheshire County"

NY person: "Wut? I thought that was some shitty town in Conn..."

NH person: *slaps forehead with hand*
by Olli Vee April 06, 2010
the classical belief was that cheshire was a type of smile. However, urban slang used in the bad ass suburbs of hertfordshire uses the expression to express their distaste for someone. It becomes a derogitary term usually used for a snitch, e.g. a grass, rat, tatletail, fibber or ragbag
Don't cheshire on me, or i'll tell veryone your a cheshire
by mad ali May 12, 2005
A really rich town in Connecticut that belongs in fairfield county. Everyone's parents are either CEOs or VPs. All the guys wear polos from lacoste or ralph lauren and all the girls have lots of accessories from chanelle, prada, dolce gabbana, and coach and loads of jewlery from Tiffany and Cartier. Nobody knows what a knockoff or a sale is and most of the houses price well into the millions. Everybody owns at least 3 luxury cars. Everybody spends their summers in Cape Cod, Nantucket or at a snobby Country Club where they play golf and tennis. And everybody is white.
I wish i lived in Cheshire cuz then i'd be rich.
by J. J. Smith November 23, 2007