I think it is best to dress appropriately for the situation.
If I am going for a morning exercise walk, I will wear sweats and tennis shoes. If I am going into SF for the day to walk Pier 39, jeans, tennis shoes, and a thick coat. If I am going wine tasting, some comfy dress. If I am staying home, then maybe some items I would never post on my blog
I don't know so much about dressing your age. I think that is rather demeaning. Two things I try and think about when I dress, first - does it actually look good as in, does it actually flatter my body and looks and secondly - is it appropriate for what I am doing. My birthday party dress for example is not so appropriate for shopping at Costco.