'Shadiest' definitions:

Definition of 'Shadiest'

From: GCIDE

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]