I'm having the same problem - soulful eyes that can show genuine mourning does not go well with a 'plain' face.
I'm a normal (ie, plain, lost in a crowd) looking person, not a Hollywood actress. And when I cry, I look quite ugly and a mess
😛 Someone who can portray what we are looking for is *much* more likely to be stunningly beautiful, but I think the veil can help mitigate that.
As an example, I suggest Monica Bellucchi (perhaps more Italian than we'd asked for?)
She's the doctor in 'Tears of the Sun,' and she's Mary Magdalen in 'The Passion of the Christ'. For a non-teary role, see her in the Matrix sequels.
No one would ever describe this woman as 'plain':
And yet, dirty her up a bit, and she can act through that:
So, yes, I'm willing to ease back on the 'not very pretty' requirement, and use the costume to make her more 'lost in a crowd'.