I am posting this after reading a wife's post asking other wives, among other things, the following: "...so what do I say when he asks me if he looks good (meaning feminine or like a women)? What do I say when he asks me if he looks good in the dress he is wearing? ... But I just don't know what to say. ...And then I also feel that if I say he looks great, it encourages the behaviour more."
Well, those of us who are fortunate enough to have wives who both know and are willing to offer a critique, we are VERY lucky. Objective criticism helps a lot. (Cross dressers, feel free to chime in here.) Most of us have been in the closet so long that we just don't know what looks good. I can't tell how hard it is to match a top and skirt that aren't solid and primary colors. I have often said that cross dressers need women's geramimals. Remember the clothing line for boys that all you had to do was match the animal on a top and pant? Anyway, I digress.
So what should wives say if asked the question above? First, be honest. IF the CLOTHING looks goo,d say so. If it looks bad, say so. Don't worry about hurting his feelings, you are helping him. In either case tell him why. What worked or didn't. The same applies to questions about makeup or "passability." My wife will always compliment or critique an outfit I ask her about and without a comment on my makeup. My typical question is, "Does this look like something a normal woman would wear?" (kind of cracks me up to write that.) If I specifically ask about my makeup, she is equally honest. Once or twice I asked her if she saw me on the street would she instantly know I was a man and she gave me an honest opinion.
Cross dressers need honesty, not false praise. You are a wife, not a cheerleader. Honesty will teach him AND temper the pink fog.
Good luck wives.