I've noticed at work (a 28-day residential recovery center in a Seattle suburb) that a majority of the women, of all ages, are wearing dresses that come to at least mid-calf. Combined with bright colors and some nice jewelry, it gives them a San Francisco in 1967 look. Frankly I find it VERY attractive.
I think the problem with JW style clothing is not the clothing per se, it is the fact that they are frumps on the inside. The last two to show up at my door looked like their faces would break if they smiled. Their attitude and bearing would have been unattractive no matter what you did with their apparel.