Great question Stephanie,
As I am not retired yet I do not have a answer. But like others have made clear each families situation is different, so I imagine that there is no one answer that fit all. It does seem that having a wife that is accepting (within limits) is a good starting place. I agree with Micki that you should consider having the "big talk". This is never easy or comfortable but may be helpful in you and your wife finding what could work for you both. After my wife and I had our "big talk" I found we became closer. My wife never ws happy about my dressing desire but I believe she has made a great effort to try to understand and I believe she can accept my needs to dress within limits. My wife does, on occasion, ask if I need a dressing day and has accommodated me. I feel if I ask for a day to dress she would be willing to support that (within reason). Might work for you and your wife.
Best wishes to you and your wife finding the path that works for you both.
