1) (n.) A thick wool sock worn in the wintertime (pl. woolies)

2) (adj.) Describing an untrimmed moiety of superfluous hair surrounding the penis
1) Gee, Dan, those woolies must be coming in handy here in Canada! Say, how much did you pay for those woolies?

2) My friend doesn't believe that it is essential to trim pubic hair, claiming, "it's natural". What is natural is that he's got some microorganisms growing right in the thick of his wooly unit.
by UnitMasterFlex February 15, 2008
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To think any female is of an attractive quality.
"she's a right 5 pence".... Shut up Jordan your such a wooly, she's a train wreck.
by Wizard of Wordary October 12, 2018
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A cheat 50 cent drink found in New York
Which is called a Tropical Fantasy
“Bro are you really buying a Wooly, bad bev
by NYC’S BEST April 8, 2019
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A wooly is short for the Liverpool term Wooly Back which is a derogatory expression for people from lancashire and cheshire, originating from the early 1900's when the population of lancashire used to wear a form of sheepskin coat and was considered to be a sheep shagger by scousers.

This of course has not changed much, except the lancashire and cheshire fashion sense has got worse
see wooly back or manc or sheep shagger or wool
by Tommy w October 5, 2005
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Wooly are the best shaggers to ever roam the land, if you ever want to get the best sexual experience, ask a Wooly. They can make you feel pleasure like no other. They can also be extremely kind, sweet but also arrogant towards certain things.
Damn, I really wish I could've shagged Wooly.
by w0oIy August 25, 2020
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The weatherman said it's gonna be -30 tomorrow... you better put your woolies on!
by Sam Scarma July 28, 2005
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