Green’s Dictionary of Slang

raggedy adj.

also ragidy, raggety, raggly

(US black) run-down, second-rate, dilapidated; of emotions and objects.

[US]Eve. Capital Jrnl (Salem, OR) 29 Sept. 4/1: ‘Ain’t you ashamed to be seen in der tabernacle in such raggedy pants?’.
[US]Arizona Republican (Phoenix, AZ) 16 Mar. n.p.: Your old man’s a mean guy [...] He’s a tailor, and yet, he lets you wear those old, raggedy pants.
[US]Z.N. Hurston Mules and Men (1995) 146: I’m raggedy, but right; patchey but tight.
[US]W. Guthrie Bound for Glory (1969) 389: I wrote up a lot of songs for union folks, sung ’em all over [...] from th’ padded studios of CBS an’ NBC to th’ wild back country in th’ raggedy Ghettos.
[US]W. Fisher Waiters 285: An’ where’ll I be? Out there on my raggedy ass.
[US](con. 1950s) H. Simmons Man Walking On Eggshells 204: Can you imagine a stud like me, who used to be one of the baddest mammy-tapping gangleaders in this jive town, now trying to uphold the law in this raggedy jive-ass city?
[US](con. 1930s) R. Wright Lawd Today 58: He’s raggety’s a dime mop.
[US]H. Rhodes Chosen Few (1966) 41: Say, your platoon sho’ looks ragidy, don’t it.
[US]V.E. Smith Jones Men 185: People [...] tellin’ me my shit gettin’ raggedy.
[US]J. Allen Assault with a Deadly Weapon 188: We take the keys [...] and go on out to my old raggly car.
[US]H. Gould Fort Apache, The Bronx 103: Filthy Freddie, a raggedy bum who lived in the garbage cans on Westchester Avenue.
[UK]J. Baker Walking With Ghosts (2000) 275: A man with a raggedy beard.

In compounds

raggedy Ann (n.) [play on Raggedy Ann, a children’s doll]

(US black) an untidy, unkempt woman.

[US]E. Folb Runnin’ Down Some Lines 144: Expressions like raggedy, raggedy Ann, [...] carry with them, among other things, the image of badly made goods.
raggedy-ass ride (n.) [ragged-arsed adj. (3) + ride n. (2a)]

(US black) an old car, any form of motor vehicle that has become run down and dilapidated.

[US]Billie Holiday Lady Sings the Blues (1975) 55: I’d have to travel five hundred to six hundred miles on a hot or cold raggedy-ass Blue Goose bus.
Luniz ‘Dict.’ at [Internet] Hooptie: Under Car, Bucket, Raggedy Ass Ride.