First, let me dissuade of the idea that I am a pastor. And, if I ever become one, much to the dismay of some I can also assure you that I am not infallible.
Second, how I would go about welcoming someone with less than modest dress and gently and lovingly teach them to value themselves more highly and dress appropriately would be done in the same way any one else that I know who espouses a strong view on modesty. My acceptance of them is not based upon their way of dressing. They have much more value as a Christian and a garden variety pagan, which ever they may be, than in the way they dress. So, I would never accept or not accept a person based on the way they are dressed. It is not a ground for so doing. Then I would in a way that might take years do as you indicate gently and lovingly teach them. I am a little iffy about what you mean by value themselves more highly, but that aside, it would be over time. You think I always held this view? I learned it, so can others.
As for your other questions, let me say wearing certain things and acting a certain way are a large element constituting modesty. I will be the first to say/admit/recognize that modest is first and foremost a heart issue for men and women. Nevertheless, I will put it this way. I used to be on the campus of a certain very well known Christian University (which will remain anonymous) on occasion with the standing rule, a rule stringently enforced, that girls had to wear long dresses. Now these dresses were, I think again by rule, were virtually down to the floor. Many, however, who wore these dress were not modest women. Why? Because they knew the art of sensuality. They oozed with sensuality in the way they wore their hair, the way they walked, the way they wore the slightest makeup, and the places in which their dresses fit most snugly. So, did the clothes alone make them modest. No. So, it is wearing and acting, but even more importantly it is the heart.
As for what is modest for men, I think several post here have documented that issue well. For women in our culture, it is a bit more of a challenge so I offer some suggestions that will be of benefit from my perspective.
They are seen in what is commonly called the “Modesty Test”. A simple Goggle search will find you plenty of them. However, in all honestly, I really am not that convinced that Christian women are prepared to subject themselves to it. The test itself will, therefore, be easy for most to dismiss, especially when it infringes upon the way they want to dress. (I guess I better make a disclaimer here: This post is not meant to be indicating you personally or any other person who may think so, since I have never met you or anyone else that might think this post is directed at them personally
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