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Douglas Harper's Etymology Dictionary
wooly

also woolly, 1570s, "resembling or made of wool," from wool + -y (2). Meaning "barbarous, rude" is recorded 1891, from wild and wooly (1884) applied to the U.S. western frontier, perhaps in reference to range steers or to unkempt cowboys. Related: Wooliness.

Wiktionary
wooly

a. (context US English) (alternative form of woolly English) n. (context US English) (alternative form of woolly English)

WordNet
wooly
  1. adj. having a fluffy character or appearance [syn: flocculent, woolly]

  2. confused and vague; used especially of thinking; "muddleheaded ideas"; "your addled little brain"; "woolly thinking"; "woolly-headed ideas" [syn: addled, befuddled, muddled, muzzy, woolly, woolly-headed, wooly-minded]

  3. covered with dense often matted or curly hairs; "woolly lambs" [syn: woolly]

Wikipedia

Usage examples of "wooly".

You can see patches of dead hemlocks, probably killed by the wooly adelgid, which is infesting so many of our forests.

Farmers battled Terran immigrants like tarnished plant bugs, sawflies, wooly aphids, coddling moths, leafrollers, lesser apple worms, and the arch enemy: plum curculio.

In place of the lean, vulpine Crandal, a softer, woolier twin appeared.

It streamed down off the great ice fields where, Ingold said, the sun had not shone in a thousand years and where not even the wooliest mammoth could survive.

I looked down with regret at what I was wearingmy oldest, wooliest, warmest robe, a garment so unfashionable in appearance that it could not even be called a dressing gown.

A certain industrial concern whose initials are LockLever is pressuring a Texas rancher to sell his whole spread, which LockLever will turn into the wildest, wooliest, modernest dude ranch in the world.

While he cinched the saddle snugly in place, Dove snuffled over the thick, wooly pelt that lined his shearling coat.

A young man was strapped into the chair having a wooly afro conked into a fifties process.

I thought Tombstone wild and wooly, but from what I have seen, Bisbee is even worse!

Ay, he who so swayed a will of a wisp before me, hand prop to hand, prompt side to the pros, dressed like an earl in just the correct wear, in a classy mac Frieze o'coat of far suparior ruggedness, indigo braw, tracked and tramped, and an Irish ferrier collar, freeswinging with mereswin lacers from his shoulthern and thick welted brogues on him hammered to suit the scotsmost public and climate, iron heels and sparable soles, and his jacket of providence wellprovided woolies with a softrolling lisp of a lapel to it and great sealingwax buttons, a good helping bigger than the slots for them .

Ay, he who so swayed a will of a wisp before me, hand prop to hand, prompt side to the pros, dressed like an earl in just the correct wear, in a classy mac Frieze o'coat of far suparior ruggedness, indigo braw, tracked and tramped, and an Irish ferrier collar, freeswinging with mereswin lacers from his shoulthern and thick welted brogues on him hammered to suit the scotsmost public and climate, iron heels and sparable soles, and his jacket of providence wellprovided woolies with a softrolling lisp of a lapel to it and great sealingwax buttons, a good helping bigger than the slots for them, of twentytwo carrot .

He looked at her legs, their taut sweep from wooly sock tops to the sandpapered fringe of cut-off jeans.

That's put on your warm woolies, friends, sneak out the dog-doer, and set fire to that gimcrack by band, yourselves, tonight.

In every letter that came fluttering Harry Liebenau's way -- four in January, in February only three -- Jenny wrote some thing about slowly growing woolies: "In between I've been working hard.

And it wouldn't matter what mad color the pranksters painted the woolies, there's not a color in the rainbow that my people don't like.