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A high school in Connecticut full of people who think they're better than you. Cheshire kids are upper middle class, and they love to show of their "wealth" with nice cars and expensive clothes. The brands people wear there are hollister, abercrombie, ugg and northface. The girls all think they look sexy when they wear ugly, butt-hugging skirts and trashy low-cut tops. The girls also wear these yoga pants that are always too tight to try and get guys to look at there asses. Even the fat ones wear this shit. Cheshire kids like to brag to kids in other towns about how the education they are receiving is "top notch", but really its just the average crappy high school. Its actually probably worse because of the asbestos and various plumbing problems. The kids at Cheshire high all think they're bad-ass "chettos"(a term for someone living in the Cheshire ghetto) because occasionally someone from the school gets arrested for drugs. There is a cop stationed at CHS at all times. The area by the tennis courts is a place were the Cheshire druggies smoke weed, drink, and have sex, all in broad daylight. The cop at CHS is too stupid to go down there and arrest them, which is considered "hiliarious" to the rest of the students. Cheshire high students are always bitching about there problems on facebook, and posting stupid-ass photos of them in the bathroom mirrors of CHS. All the Cheshire peoples' stupid facebook drama clogs up everyone elses news feeds.
"Chetto" 1: yo dude, lets go hangout by the tennis courts at Cheshire High School

"Chetto" 2: nahh bro i heard all shorts of shit happens there
by Theonlynormal1 January 24, 2012
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A school full of people who think they're the shit; CHS has girls with big titties and some flat chesters too. But no matter how good you look, as a girl, you must wear clothes that make men's lightsabers enable. They all think they live in a schetchy area because a kid got arrested for selling drugs once. They like to show off their wealth by wearing expensive clothes and having more expensive cars than your mom or dad.
CHS kid: I got a gucci belt bro!
Wallingford kid: I got food today!
Wallingford parent: Those Cheshire High School fags
via giphy
by Niggaraguacamole September 27, 2018
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