Etymology
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shady (adj.)

1570s, "affording or abounding with shade;" 1590s, "protected by shade, sheltered from glare or heat;" from shade (n.) + -y (2).

The meaning "disreputable" (1862) might be from or reinforced by the earlier university-slang sense of "of questionable merit, unreliable" (1848, perhaps on the notion of "such as cannot bear the light"). Related: Shadily; shadiness. Old English had sceadlic "shady" ('shadely'); the Elizabethans also had shadeful. Colloquial on the shady side of "older than" (a specified age) is by 1808.

updated on July 22, 2022

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Definitions of shady from WordNet

shady (adj.)
quiet, dark, or concealed;
her shady past intrigued him
a shady part of town
shady (adj.)
not as expected;
a shady deal
Synonyms: fishy / funny / suspect / suspicious
shady (adj.)
of questionable honesty or legality;
He established a dummy company through which he laundered vast sums of cash from shady middlemen and arms dealers
shady (adj.)
filled with shade;
the shady side of the street
Synonyms: shadowed / shadowy / umbrageous
From wordnet.princeton.edu, not affiliated with etymonline.