My opinion: It depends on what she feels comfortable with. If a
favourite dress or one that suits a bold personality has a low
neckline, and she isn't afraid to show it, go ahead. The same goes
for less revealing attire.
It won't work though on those guys who want to believe that they
are dating Miss Goody-two-shoes.
It also depends on where they are planning to go, whether it's the
beach, a restaurant, or a place of worship. Wear what is practical
and adheres to the dress code.