I'm a similar age OP and I've been thinking about digging out some of my shorter dresses and skirts for winter, to wear with tights and boots. Though probably ankle or mid-calf rather than long boots. I don't normally really stick to fashion but it affected me enough to stop me wearing them somehow! But now they seem to be a thing again and I like the look too.
I think shorter skirts on older women is a good look - I might not want to go super short or get my bare legs out at this point, but it can be a great winter look. As a student I went to see Germaine Greer speak and was impressed with her short skirt and tights! - she would have been in her 50s.