1. most full of shadows; darkest or most shaded
Usage: superlative form of shadowy
2. most vague, unclear, or mysterious
Usage: superlative form of shadowy; figurative

Examples

• The shadowiest corner of the garden was perfect for hiding.
• We explored the shadowiest parts of the old castle.
• His explanation was the shadowiest of all the witnesses’ accounts.
• The shadowiest details of the plan remained unclear.
• She retreated to the shadowiest spot under the trees.
• The shadowiest aspects of the case puzzled investigators.