Being timid, coolly robbed of some dollars (3)
I believe the answer is:
coy
'being timid' is the definition.
('coy' can be similar in meaning to 'timid')
I don't understand the rest of the clue.
(Other definitions for coy that I've seen before include "Pretending shyness" , "Pretending modesty" , "reluctant to divulge information" , "Pretending to be shy or embarrassed" , "not forthcoming" .)