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From: Webster's Revised Unabridged Dictionary (1913)

 Shad·y a. [Compar. Shadier superl. Shadiest.]
 1. Abounding in shade or shades; overspread with shade; causing shade.
    The shady trees cover him with their shadow.   --Job. xl. 22.
    And Amaryllis fills the shady groves.   --Dryden.
 2. Sheltered from the glare of light or sultry heat.
    Cast it also that you may have rooms shady for summer and warm for winter.   --Bacon.
 3. Of or pertaining to shade or darkness; hence, unfit to be seen or known; of questionable character; unsavory; equivocal; dubious, corrupt, or criminal; as, a shady character; -- of people or activities. [Colloq.] “A shady business.”
    Shady characters, disreputable, criminal.   --London Spectator.
 On the shady side of, on the thither side of; as, on the shady side of fifty; that is, more than fifty. [Colloq.]
 To keep shady, to stay in concealment; also, to be reticent. [Slang]