My Dad has his wax kit and a monogram that he uses to emboss. I'm hoping he passes it on one of these days. He typically uses his for greeting cards and thank you notes. The kit was actually his grandfather's, who served in the Royal Navy. Sorta makes it cool, although I don't think I'll ever feel comfortable using it.
Can't really say, but I'm afraid of coming across as too pretentious without the... charm and elegance to back it up with. When I think of my father or my grandfather, they belonged to a different class of men -- meticulous and yet possessed of a certain panache. The shoes, they feel too big.