I think it makes sense to add a Wine icon (emblem?) over top of the
exe's built-in icon, to indicate that it's going to be run under Wine.
If the exe were going to be run through something else (CrossOver? a
virtual Windows machine?) then it could have a different emblem
representing that.

If nothing is installed that can handle .exes, I think it should still
show the exe's built-in icon, but have a "no action" emblem.

-- 
Use embedded icons for executable files
https://bugs.launchpad.net/bugs/292504
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