I have a few pieces that belonged to my grandmother, and a great aunt. Both were stylish women in their time and there was nothing old or matronly about their wardrobes. My grandmother left a closet full of elegant cocktail dresses and evening gowns from the 1950s and '60s that are just as much a delight today as when they were new. Alas, there were only a few that fit me, and the rest were sold. But skipping a generation (or two) isn't always a guarantee of a fashion disaster.

- Diane