As an alternative to wearing an undergarment he expects a dividend (8)
I believe the answer is:
investor
'he expects a dividend' is the definition.
The answer is a person as well as being a singular noun. This is suggested by the definition.
'as an alternative to wearing an undergarment' is the wordplay.
'as an alternative' becomes 'or' (I've seen this in other clues).
'to' is a charade indicator (letters next to each other) (I've seen this in other clues).
'wearing' becomes 'in' (as in being 'in' certain clothes).
'an undergarment' becomes 'vest' (vest is a kind of undergarment).
'in'+'vest'='invest'
'or' after 'invest' is 'INVESTOR'.
Can you help me to learn more?
(Other definitions for investor that I've seen before include "Financier" , "One putting money into financial scheme" , "One putting money into shares, etc" , "One with stocks/shares" , "he speculates" .)