You know, that LBD I posted is a forgiving one, size wise. It doesn't have a defined waist, so you can lose or gain weight and it will just lengthen or shorten a bit. But, it doesn't look like a sack because it drapes so well. It's really quite versatile.
It might be nice to have something like that for weddings and funerals. I personally don't wear black to weddings, but that has become extremely common; and with a white background long floral print scarf, that dress would look positively cheerful. All by itself it would be fine for funerals and for any evening event. (I personally only wear black to family funerals, I know I'm old-fashioned in that; but most people wear black to all funerals now. If I were wearing that dress to a funeral, I would put a sober dark but not black jacket over it. Or I would wear it with a somber scarf.)
IOW, I think that if you invested in something like that, you'd find a bunch of uses for it over the years.
For shoes, I would suggest these--they are very cushy and have wide toeboxes but are also nice looking enough for typical occasions. http://www.earthbran...llet-flat/42949
But I think it's best to find your own shoes that are comfortable. Basically, you want dead black leather, for most versatility, and flats if you don't normally wear heels, so that they will be comfortable. Having the dead black leather makes flats seem more polished. You can also go with black patent leather, but it doesn't stretch like regular leather does, so you have to make double sure that it's very comfortable before you take it home.