I never considered my mom's or sister's clothes as anything to be desired. They never had a style that seemed attractive. Very plain.
Moving on to my marriage, it was a couple of decades before I ever felt an inclination to try any of her things on. When I did try on a couple of her cuter items, it just didn't do much for me. Even though i did try on various items out of curiosity, I would never define myself as a crossdresser at that time. To answer the specific question from the OP, to the best of my memory, i tried on a white dress that my wife had only worn once or twice. It was not fitted at all. I didn't hate it on me, but, at that time, it didn't bring any real desire out. It was only curiosity that was totally satisfied and not repeated for years.
After some major trauma over several years in my fifties, I developed a very clear inclination to want to wear things I'd never even considered as an option or even desirable up until then. When I began experimenting, I found a sense of 'rightness' and a sense of strength that still seems unfathomable. Now, half of my wardrobe is from the woman's department and, since I've retired, well over half of my time at home is spent in things from the femme part of my closet.
