leer·y

1 [leer-ee]
adjective, leer·i·er, leer·i·est.
1.
wary; suspicious (usually followed by of ): I'm leery of his financial advice.
2.
Archaic. knowing; alert.

Origin:
1790–1800; leer1 + -y1

leer·i·ly, adverb
leer·i·ness, noun

wary, weary, leery.
Dictionary.com Unabridged

leer·y

2 [leer-ee]
adjective, leer·i·er, leer·i·est.
leer2.

Origin:
leer2 + -y1

Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2013.
Cite This Source Link To leery
00:10
Leery is always a great word to know.
So is quincunx. Does it mean:
an arrangement of five objects, as trees, in a square or rectangle, one at each corner and one in the middle.
a calculus or concretion found in the stomach or intestines of certain animals, esp. ruminants, formerly reputed to be an effective remedy for poison.
Collins
World English Dictionary
leery or leary (ˈlɪərɪ) [Click for IPA pronunciation guide]
 
adj , leerier, leeriest, learier, leariest
1.  dialect chiefly knowing or sly
2.  slang (foll by of) suspicious or wary
3.  slang rowdy or boisterous
 
[C18: perhaps from obsolete sense (to look askance) of leer]
 
leary or leary
 
adj
 
[C18: perhaps from obsolete sense (to look askance) of leer]
 
'leeriness or leary
 
n
 
'leariness or leary
 
n

Collins English Dictionary - Complete & Unabridged 10th Edition
2009 © William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009
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Etymonline
Word Origin & History

leery
"untrusting, suspicious," 1718, originally slang, probably from dialectal lere "learning, knowledge" (see lore), or from leer (v.) in some now-obscure sense.
Online Etymology Dictionary, © 2010 Douglas Harper
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Example sentences
Be leery of e-mails claiming to show pictures of the disaster areas in attached
  files, as the files may contain viruses.
Hospitals leery of making treatment records available online to their patients.
Be leery of any contractor that wants you to pull the building permit.
And plenty of people are too leery of the economy to take the homeownership
  plunge now.
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