I have learned to be very cautious with my wife, never bringing up my dressing unless she does, at which point I will discuss anything she wants.
What's interesting is that, even before I came out to her (and restarted my CD'ing) we had the kind of relationship where we shared a lot, including her own fashion choices and those of her friends. Maybe because subconsciously that side of me was always responsive to that?
So with a family wedding coming up, and the idea that everyone will dress 'vintage', she showed me a picture of the 50's dress her best friend had bought, which happened to be exactly the kind of dress I want to find for myself (and her friend is the only other person that knows of my dressing, coincidentally). It was all I could do to not express my own desire to wear that dress, even as I told her how much I liked it. I know my wife, and I think that if she wanted to discuss my dressing, she would have been direct.
The capper came when she told me about the petticoat that her friend had bought to wear under it. That sent me through the roof! Maybe I'll have to ask her friend if I can borrow it after the wedding.
<sigh>