Great insights and conversation here. These days I'm conscious of keeping these things in perspective and keeping judgment out of it. I am less and less worried about 1) what anyone else chooses to wear, and 2) whether other people like what I wear. I want to look "good" and current and not older than I am, sure, but I'm not putting a *ton* of energy into these efforts, mainly because I have a wardrobe that usually allows me to pick out something I feel good in. But I will always put in effort according to how I feel.
One of my best friends watched his wife slowly die of cancer last winter, after 17 years of battling on and off. She was always a gorgeous woman who ate right, worked out, and dressed beautifully for as long as she could. Disease gradually robbed her of most of her bone mass, half a lung, and about four inches in height. Right up to the final months of her life, she still made an effort to look nice, and I know it bothered her that she could no longer wear her beautiful clothes from her old, healthy body, but that paled in comparison to the fact that she wanted to see her four children grow up. She did live way longer than any medical professionals thought she would at the time of her diagnosis.
So I understand what many of you are saying about dressing an aging body, and keeping it all in perspective. My mom lived to be 80 (which doesn't seem all that old to me), and dressed nicely right up until the day she went into the ICU because she was able to. As long as I am able, I will make an effort too.