[1] : The Collaborative International Dictionary of English v.0.48

shady \shad"y\, a. compar. shadier; superl. shadiest.
   1. abounding in shade or shades; overspread with shade;
      causing shade.
      1913 webster

            the shady trees cover him with their shadow. --job.
                                                  xl. 22.
      1913 webster

            and amaryllis fills the shady groves. --dryden.
      1913 webster

   2. sheltered from the glare of light or sultry heat.
      1913 webster

            cast it also that you may have rooms shady for
            summer and warm for winter.           --bacon.
      1913 webster

   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." --london sat. rev.

            shady characters, disreputable, criminal. --london
                                                  spectator.
      1913 webster

   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
      1913 webster
see also:
shadier shadiest on the shady side of to keep shady 

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