would your father be proud of you
not only no but hell no. When i was 10yrs old and got caught by my folks wearing my mothers skirt, my father said that real men don't wear skirts,and he also said that i was sick in the head. He thought that i was sick in the head until he died about 5yr ago.
Add me to the "Nope" list
My dad was a pretty conservative, hard-working, hard-playing man who didn't approve of my look during my "hippy" years. He didn't realize that when he left my mother, he removed the best male role model around. Mom became the one that I followed and emulated. She wasn't too happy when she found out I'd been trying on her clothes and sent a 13-year-old me to stay with Dad for the summer. I don't think he knew why I was there. We never talked about it. Based on everything I knew about him (he's been dead for 15 years or so), he may have been proud of my education, career and my ability to build things or play ball, but not crossdressing. His may have been the "greatest generation", but it wasn't the most understanding one.