A woman wants to know if something looks good on her. Personally, I hate it when my husband doesn’t say something if I pick out an outfit and then go out in public only to find out later that I made a poor choice in an outfit, for whatever reason. Wives, in my opinion, ask this question for two reasons:
To boost their self-esteem by gaining approval of the one man who really matters;
and because they really care about how they look.
With these issues in mind, the correct answer is neither yes or no if the outfit is unbecoming. To say “yes” would be cruel and certainly doesn’t help a woman’s self esteem and to say “No” according to the second issue, would allow a woman to go out looking less attractive.
So, if the outfit really is not becoming, then tell her, “My favorite outfit is …whatever, red dress, white shirt…etc.” Make sure it really is a nice outfit on her.
It will inevitably lead to a discussion about why you would rather she wear your favorite outfit than the one she has on. Then you have an opportunity to compliment her. Tell her what you really like about her in that outfit: the way it shows off her softness, her curves, makes her look feminine and turns you on, etc. It is especially effective if you can hold her and cuddle with her at the same time, sweetly touching her face, placing your hand lovingly on the small of her back.
You will be honest in that you are making sure she doesn’t wear something unbecoming and at the same time helping her find an outfit that does look nice while boosting her self esteem.
Trust me, it works. I use this technique on my husband, too.