What Should I Wear?

That is the age-old question every woman asks themselves any number of times during the year. And the answer to that gets more difficult with each passing year.
When I was a younger version of my self, you could find me in the Juniors department. A bit later, I graduated to "Misses", but still could wear just about anything. However, there comes a time when those clothes aren't quite right anymore. I came to this realization a few years ago in the dressing room of one of my favorite stores. My body had changed, but my fashion mindset hadn't caught up yet and I found myself trying on clothes that, in the day, would have looked great, but, unfortunately, now made me look foolish. Let me explain that I haven't gained a ton of weight; it's just that it redistributed itself around my body (and not to my advantage). It seemed to happen overnight, but I know that wasn't the case.
One of the things that disturbs me is seeing a woman wearing age inappropriate clothes. I worked with a beautiful woman who was definitely trying to hold on to her youth, wearing short, short dresses/skirts, and little, babydoll blouses that did nothing for her and distracted from her pretty face.
Why don't men have this problem? Most department stores divide the women's clothing into 4 areas - juniors, misses, womens and petite. My husband is confused by that. He doesn't understand that he should NEVER buy me anything from the Women's section.
There are some things I won't give up - jeans and t-shirts, to name a couple.
So, time goes on and things don't change. I'm attending a special event this week. Now what should I wear?