To each, their own.
I don't necessarily think age matters either.
I think I can understand why you would like to ride that way. I can see where it could make an individual feel more relaxed, cool (temperature), free or whatever adjective you want to use. I tried it twice, meaing I rode in just jeans boots and a T-shirt, as compared to my typical armored jacket, chaps and a helmet.
But I have always enjoy sports where I have to put on "gear". Football, lacrosse, mountain and rode biking and now MC riding. Having well fitting and functional gear is a part of my enjoyment and separate from the protection they offer. They make an obvious link to what you are doing, for me. You see a rider enter in full leathers and a helmet, I think: they are serious about what they are doing. A sense of commitment and pride in their hobby/recreation/way of life. If I see "weathered" gear over new, I think, "Veteren rider".
You roll in wearing short and flip flops....I don't know.....
I know I am making some judgements that could be incorrect and I am not saying I act on them. Only my initial thoughts, is all.