If there's anything I've learned at the ripe old age of 25, it's that you can't dress, act, or behave in a way simply to please others... it's time consuming, not worth the effort, and silly IMO.
At the end of the day, if what you are wearing or carrying (hell, it could be a Cambon when you're 90, a classic flap when you're 15, who cares) is something YOU love it and makes YOU happy, then that's all that truly matters.
While I do think some bags may be more classic than others, I don't think bags have an age attached to them at all (just a too high price tag hehe)!
Speaking of clothing, my mom's friend is twice my age, and she pretty much buys everything I buy, and even gave me her credit card number to shop for her online haha... I think it's great, because it makes her happy, and she rocks whatever she's wearing (luckily, we don't frequent a lot of the same places... otherwise, it could be double vision haha)!
So sure, if I see someone who is dressed inappropriately IMO (say, a micro mini and a tight "wow, that leaves nothing to the imagination" top at 70), I may think wow, because it's human nature to stop and look at something that catches your eye, in whatever capacity that may be. If that person is happy though, then good for them, hey... and what pleases one may appall another, plus who am I to judge anyway.