Raggy is a term of unknown origin dating back to at least 1965, widely used in the northwest corner of Connecticut to describe someone who was born or residing in (but not limited to) Winsted, Connecticut.

The term "raggy" is generally limited to someone between the ages of 12-25, past the age of 25 it is widely agreed the raggy graduates to being white trash

A typical raggy can be found riding their stolen black spray painted BMX bike in the downtown areas of Winsted and surrounding micropolises (Torrington also being a raggy hotspot).

The characteristics of a raggy are constant from each offender. Your standard raggy can be found wearing an 80s metal t-shirt, or the latest t-shirt from hot topic displaying an ironic slogan on the front. Along with their nonexistent sense of style, raggies can generally be found with hair that has been uncut for the better part of a year, and sporting spotty facial hair that badly needs to be shaved (see rat stache).

A raggies hygiene seems to be almost nonexistent; it is not a stretch to say that raggies do not bathe for days, if not weeks, at a time.

A raggies home life can be described as turbulent at best. Amateur sociologist’s research has concluded that the raggy bloodline generally extends through numerous generations, and the typical raggy stems from unloving alcoholic parents and succumb to this gruesome subculture as a way to get back at their guardians, unknowingly taking the paths that their parents took when they were youths.

Raggies have historically not taken well to the educational system, and surmised research has been conclusive in stating that the average dropout rate of a raggy is upwards of 67%. This lack of education can effectively attribute to a raggies lack of income later in life. It seems that this high dropout rate goes hand in hand with a raggies lack of respect for authority, only creating more trouble for them in their devious path of life.
Kid #1: Did you go to the OPOT show last night?
Kid #2: Yeah for a few minutes, that place was raggy central!
by tetrahydrozoline HCI April 28, 2007
A term similar to the "N" word in its power to insult, unique to Northwest Connecticut. Refers to lower than low white trash. Winsted residents are sure it refers to some people from Norfolk. Norfolk residents think raggies come from Torrington. Torrington people believe that raggies live in Winsted. And so on.

At the Greenwoods School in Winsted, calling another kid a "raggie" was cause for detention. Mothers would wash the mouth of any child who used the "R" word.

White trash have a car on blocks in the yard, & a couch on the porch. Raggies typically have a couch on the lawn and a car on the porch.

Look out for a two year old raggie throwing rocks at passing traffic. (Route 44, Route 8)

by Dave Q It November 11, 2007
A shaggy fellow who solves mysteries with his friends.
Ruh-roh, Raggy!
by Tristan Sinclair December 12, 2018
Someone who does not take care of themselves, wears cheap hobo like attire like: baggy sweatshirts, long oversized t-shirts, pajamas out in public, or curlers in their hair. Often with unbrushed/uncut hair, smelly, and dirty. Does not often care about anything or acting civilized.
-Ew. I hate being around that girl. She has no sense of style and everytime she walks by she smells.
-I know right, when was the last time she brushed her hair? she's such a raggy.
by yoyoma urmom123 December 28, 2009
A typical "raggie" is a resident - life-long or import - of Winsted, CT. A typical "raggie" can be defined as follows: 1.) Enjoys everything about Cumberland Farms and The Donut Station.
2.)Can be seen regularly doing "hot laps" from BP (Now Sunoco) to Winsted Savings Bank and back in a car that is typically worth more than their house.
3.)Most raggies have a brood of offspring who they take to the annual Winsted Fireman's Carnival and parade down Main St.
4.)Most raggies, from time to time, enjoy going to Holland Beach, wearing nothing more than a wife-beater (white tank-top)and/or dirty jean cut-offs.
5.) As Winsted has the most bars-per-square-mile of any Connecticut town of it's size, many raggies have developed life-long drinking problems. This leads to loss of their licenses, increasing their dependency on bicycles for transportation of themselves and their Miller High Life.
6.)Many bike-riding raggies can be seen in Winsted typically between the hours of 8 p.m. and 3 a.m. (and at all parades and town events)
"Look at that raggie hanging out of the parking lot of the donut station"
by JessUrban August 31, 2006
Adjective derived from ragtime
this songs so raggy im floating away
by Uneliasmarsu March 14, 2016
1 . A term that is used, almost exclusively by residents of Northwestern Connecticut, in a derogatory fashion. 2. A name once given to the workers of charcoal pits on Mt. Riga, located in Salisbury,CT, to label those who were of a poor working class ( mostly Dutch immigrants ). The ash and soot from the charcoal burning pits would force these workers to tie handkerchiefs or "rags" to their faces in order to filter the acrid air. The term "raggies" refers to their use of these rags.
"Raggies would often come down from the mountain , for lunch, to eat in downtown Salisbury"
by purple octopus October 16, 2009