Didn't read the whole thread, but I personally wear the bags I love, never mind brand/age associations.
My first designer bag was Prada, and I was far from matronly age when I bought it.
I am still in love with it, although mostly with older models, rather than contemporary.... LOL!
And BTW, here in DC Metro you'll see as many fake Pradas, as LV's, Guccis, Fendis, you name it.
IMO, the wealthier the surrounding community is, as in, the higher the plank is set to keep up with the Joneses, the more designer fakes you'll see on the street. HTH!