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  • What to Wear to Date an Older Man


    Q:Help, I want to stay young while dating an older man! I have a unique, creative and daring style, but I have met someone who is polished, somewhat conservative and in a position of power and respect at work. He is a good bit older than me and I am confused about how I should dress.

    I do not want to give up my stylish side, but I feel that I need a more conservative approach due to our work. He is happy with my youthful look, but I feel that it boosts his ego and makes me look too young. I am 30 and I don’t want to dress too old or too young. Any suggestions? (Myrtle, MS)


    I would like to think that the two of you are dating because you genuinely care about each other and have a great time together. Not solely because your age difference is a mutual ego boost.

    If he needs to feel like a spring chicken again and you are on some power trip, you are most definitely writing to the wrong advice expert. Should this relationship endure, one day, you won’t be sooo young any more and he will be too much of a delusional dweeb to realize that he ain’t so studly himself… ponder that!

    How this man feels about your dress is really not my concern. It’s how you feel about yourself. Obviously, the guy is attracted to you and the idea that you feel you may have to give up your stylish side to be with him really scares me.

    If you feel that you want to look more polished, pare down the dramatic a bit. As long as appropriate, your style of dress can go with your mood-one day kooky, one day conservative.

    Certain situations and occasions do call for a more conservative form of dress than others– that’s common sense. You don’t show up at a corporate board meeting in a denim mini and a corset top. And, yes my dear, you can have a conservative, yet fashionable, style of dress. That means, ditch those silk, short-sleeve shell tops and the dowdy string of pearls.

    If you have to dress to please him, you are not really pleasing yourself. Go shopping and find some gorgeous clothes that make the most of what you’ve got… then look around some more for a more compassionate companion who accepts you for you and not just for your youthful appearance.

    –February 6, 2003

    Hankering for some image boosting advice? Ask Sharon: Advice Page


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