leery

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

Origin:
1790–1800; leer1 + -y1

leerily, adverb
leeriness, noun

wary, weary, leery.
Dictionary.com Unabridged

leery

2 [leer-ee]
adjective, leerier, leeriest.
leer2.

Origin:
leer2 + -y1

Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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World English Dictionary
leery or leary (ˈlɪərɪ)
 
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
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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
They are leery of unsolicited e-mail attachments, and careful about the web
  sites they visit.
Many employers, even in academe, are leery of providing letters of
  recommendation or references.
Despite the power of placebos, many conventional doctors are leery of
  prescribing them.
And plenty of people are too leery of the economy to take the homeownership
  plunge now.
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