1. having the most shade; most protected from sunlight
Usage: superlative form of shady
2. most dishonest, suspicious, or untrustworthy
Usage: informal; superlative form of shady

Examples

• We found the shadiest spot in the park for our picnic.
• This is the shadiest corner of the garden during summer afternoons.
• That’s the shadiest business deal I’ve ever heard of.
• He’s the shadiest character in the whole neighborhood.
• The shadiest part of the forest provided relief from the heat.
• She avoided the shadiest areas of town after dark.