http://forum.wordreference.com/threads/in-with-glasses.2499988/
The man with the red glasses could:
‧Have them on
‧Be holding them
‧On his cap on the top of his head
‧Hanging off his shirt pocket...
‧Etc.

想藉此順帶一問，earrings、bangle、bracelet這類的飾品，是用in還是with，或者如同glasses一樣用in/with有不同意思

用wearing