I'm not going to say my age (for i.d. purposes), but I am getting on. I bought my first pair of DrMarten boots this year and now I own five pairs of Doc Marten footwear. I wear them with anything and everything, eg jeans, skirts, dresses, and it doesn't matter whether I'm dressed up or down; I wear them. I used to be so wrapped up in how I looked [thank god this was before the age of the internet], but now nobody is going to be admiring me for my looks at my age (except perhaps to say, she looks good for an elderly woman).
I had a period of knowing I was now invisible, as far as the 'male gaze' was concerned. I was middle-aged, and then I went through the menopause. Once I got over that thing of not providing what was needed from a woman by society it freed me up. If I love what I'm wearing than I'm happy in myself when I'm out and about. Far rather have people look at me and think, 'What does she look like', than sit around blending into the background with a male short haircut and clothing designed for women 'of a certain age'.