I'm saying no, but not on age grounds. It's because I find them quite difficult to match with clothes.
I have tried with over the knee boots, many times. I always admit defeat and send them back. The last time was about three years ago when Jimmy Choo did some black leather over the knee boots that were kind of elasticated around the knee joint. I didn't buy those (£850) but good old Karen Millen did an acceptable knock-off, so I ordered those.
No, just no. They looked like waders with trousers, and although my legs are quite thin they looked like black leather sausages; no matter how good quality the material, leather and suede are going to sag. I suspect that's what the elasticated bit was intended to counteract.
Couldn't get them to work with skirts either; you need a short-ish skirt to show off the boots, otherwise why bother having them, and you can only really wear those with boots if you have opaque tights on, otherwise you risk the Pretty Woman effect. I thought about how often I wear short skirts, and the list is (also) quite short: not for work (I am a similar age to the OP and I work in one of the professions) and not particularly for going out, either.
I quite fancied the piratical/dandy highway,an look but I couldn't fit it into my life, sadly.
My ex-chief exec met Teresa May about five years ago and told me that she had over the knee boots on. Black patent, worn with puppytooth patterned trousers (he was quite the sartorialist for a 57 year old Yorkshireman). Kudos to May for carrying them off but I admitted defeat.
BTW, OP, one of my first thoughts after reading your post was, "ooh she must have had loads more pocket money and/or Saturday job earnings than me". I'm your age and I coveted suede over the knee boots on the late 80s, but I could never afford any!