I think your dress truly needs to be a costume that would only been worn for the work. Think Broadway outfits. Apparently, this tax restriction was the inspiration for ABBA's over the top outfits in their heyday.
They can just cut the left side shorter without messing with the shoulder. I have a dropped right shoulder and that is what my tailor does. In any case, it is a minor nit to pick. I always like your fabric selection coordination of your outfits.
I don't think I could make this decision in a vacuum. That is, it would have to be made in the context of the status of the wardrobe. If I had a full wardrobe that worked in any conceivable situation I may find myself in, then I would get whatever the fuck I wanted. If I have just a few suits etc. then I would err on what is the most versatile.
So, I don't know if I could answer the op's original question without a good understanding of that.
It's the opposite for me. But that could be because I've never done it alone; I've had my tailor showing me things based off my suggestions. As it happens, I usually change my mind and get something completely different that what I started out looking for. I don't have anything approaching the specific knowledge that the posters have here. I can rarely name the maker of the fabric after I've ordered it. My tailor, he remembers.Rob