Can't I "Like" Gaylene's comment?
Suz, precisely my point. I think like you. I had to look up beatle boot. Only to realize I have a pair of flat ones I adore and do wear a lot. I didn't think they were deemed "old": to me, they are very young and fresh! Pearls: I can't wear them anymore (boo).
Janet has a point: how to dress you without looking like a mutton dressed as a lamb, to paraphrase a certain other fashion website...
And on Suz's second post: so true! I inherited some of my grandmother clothes - she had made herself - and have a hard time wearing it regularly, because it is made for a lifestyle that isn't mine. My grandmother was a teacher, like me. She did teach in various parts of the country, actually, but even then, she traveled with old style suitcases and embarked on trains / boats / planes donning full three piece tweed suits - and the corresponding Richelieu Oxfords, square silk scarves, lamb leather gloves and (now vintage) handbags. But I can't establish a parallel with my grandmother the way you do. On Sundays, she went to church: I go to the gym. She taught as an authoritative figure within the "teaching paradigm": I am a child of the "learning paradigm", dressing accordingly when guiding and accompanying students, which means wearing more pants and jeans, things in which I can lean, bend, kneel, move, jump; she traveled in style: I travel in comfort, because I won't get any time to recuperate + my body typically already has a workout or two running through its vein it needs to recover from, so I will want the snooze. Then again, a snooze while travelling was unthinkable in my grandmother's times,but today, it's perfectly possible. So all this to say I am not sure about the basics for certain tasks not changing. I think they do!