There are a number of reasons why women ask this question.  It might be puzzling and plain dumb to men but that fact is there is actually several reasons why.  The most important tip that I can give to men is never say, "YES YOU DO LOOK FAT!"   If they do chunky in the outfit try saying.. "How about you try on that blue shirt that I love so much with that skirt."  Reasons why women ask "Do I look FAT in this?" They honestly want to know if they look frumpy or fat in the outfit.Â...