Why are we trying to regulate something that is at best subjective and,at worst, arbitrary and utterly meaningless?
Yes, I think that communication is key and both parties should be aware of expectations and locale for a date.
But, to split hairs between “dressy” and “wedding” clothes is both ridiculous and demeaning to both the women and the relationship you are hoping to create.
Say you’re going out to coffee, or even out to dinner. If she is hygienic and inoffensive (ie, not wearing hiking boots to a restaurant) then that should really be okay with everyone. Both the man and the woman should dress nicely within their comfort zone, for if she goes wildly out of her way to appear a stunner, how awkward will it be post-wedding when she is far more casual?
Because (and this may shock you) there are MANY women that care less about their looks than their personalities, and if that offends the male (perhaps due to the females around whom HE was raised) then either its not a shidduch, or its an issue that deserves a solid conversation.
Remember, sof kol sof, its a man and woman, really a boy and a girl, deciding to spend the rest of their lives together.
Don’t distract them with foolish rules. Its not fair.