How can I handle a sensitive executive who needs improvement in his personal appearances?
This is relatively easy. I find that people accept criticism of material things easier than they’ll accept criticism of their personalities.
One of the best ways to handle the problem is through the process of what we psychologists call “identification.” If your executive can identify himself with you—by being seen with you, by doing the things you do, by wearing the kind of clothes you wear—he can lift his sights and change his self-image and the image he presents to associates and subordinates.
~ Mortimer R. Feinberg, Ph.D., Effective Psychology For Mangers, (1965)