hi,
My 6 year old niece has some of those "paper doll" books. We bought them at our local museum gift shop. One is fashions of the 1940s and one is fashions of the 1950s. She loves them!! She is very much interested in what life in the past.
The children's play area in this museum is full of fun dress up clothes and even has a "match the people in their attire to the background photo" game. There is a roman lady, a medieval European lady, a lady from the 1600s (france I think), an Edwardian lady and a modern lady. There are corresponding gentlemen as well. There are little hints written on the back of each figure. There are laminated pictures of a scene from each of these time periods. There is a some interesting information written on the back of each of the pictures too. Match the male and female figures, then put them on the appropriate picture. My niece enjoys matching the figures correctly, but she also enjoys letting the figures visit each other's time periods and have parties etc. A game like that might be fun. You could make it yourself.
When I was young, I spent a lot of time going through old family photos with my grandmother and with my great grandmother. We talked about all of the people in the photos and I learned so much! It was so much fun spending that special time with these special ladies. I love that you are focusing on mothers/grandmothers etc. That is exactly how I began my interest in family history... with the ladies in my family!!
Dressing up in your grandmother's clothes is really fun too. I have a wild collection of my grandmother's hats (lots of feathers!!), shoes, bags, clothes etc. She kept everything!!
Good luck,
RK