What to Wear on a Date?


“I think that young men and women are so caught by the way they see themselves. Now mind you, when a larger society sees them as unattractive, as threats, as too black or too white or too poor or too fat or too thin or too asexual, that’s rough. But you can overcome that. The real difficulty is to overcome how you think about yourself.”

-Maya Angelou

When I got divorced, the thought of dating was quite daunting. It had been almost 35 plus years since I had been on a first date.   I had no idea what to wear on a  date. I was a women in her 50’s. My only experience was from was dating in my 20’s and that would not provide me with any relevant information.  Divorce changes everything, including how you dress!

My suggestions:

  1. Dress for your age. Do not try to look like a 20 year old.
  2. Dress for the body you have, not the body you want. Make sure your clothes fit properly: not too large and not like you were poured into them.
  3. Beware of wearing too much black. A few years after my divorce, I looked at my closet, it contain mostly black clothes. I must have been in a state of mourning and wore clothes that you would wear to a funeral.  For your dating outfits, wear color. Colors that make you feel good and that look great on you.
  4. Show some skin, but, not too much. You do not want to look desperate or overly sexy. Maybe show your legs or your shoulders.
  5. Do not wear really high heels. Wear shoes that you can comfortably walk in.
  6. Wear some accessories, but, do not over do them either. Try wearing earrings and a necklace or earrings and a bracelet.

The most important point is to pick your outfit and then spend the evening concentrating on your date.  Will there be date number 2?







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