I am underdressed all the time and wear outerwear around the house frequently. My wife knows and is fine with it and participates in bedroom activities when I am dressed. She has seen me in a wig and with lipstick, but fully dressing in front of her is still a work in progress. She doesn’t seem to mind, but I am still not sure.
I go out in public occasionally, but not with my wife…yet. She has never set limits, but I know she would rather not have people know, so I keep it quiet. She did say she doesn’t care what I wear, but that I probably shouldn’t be seen in public. I agree, I probably shouldn’t, but I do.
I do wear some outerwear out in public with my wife, things like jeans and yoga pants, and she is fine with that.
All in all, my relationship with my wife and dressing is very good. We have talked about it, but she never really engages and just says wear what you want. She has never discouraged me in any way but does not encourage me either. I have told her she is welcome to ask any questions she may have, and can tell me if I have gone too far, but so far it has never been an issue.
The most positive message I get from my wife is always non-verbal in that when I am dressed either in just lingerie, or in a dress with nice lingerie and heels, we have a fun time in bed and she really enjoys it.