Trying too hard - rejecting affectation in fashion

In looking around for inspiration in my search for style in middle age I've found myself put off by the artificial appearance of those who try too hard. I don't like affectation and one sees too much of it in fashion. However, I recognise that this may result from the often inflexible and reactionary nature of middle age.

Some things that grate with me - men in brogues not wearing socks (why not wear deck shoes and why make your best shoes all smelly and sweaty?), wearing a shirt and tie but with tie undone (why bother with the tie?), hats pushed too far back (wide boy), white socks with anything other than sports clothes (yuck) and finally wearing sunglasses indoors or at night (why?).

I recognise that these things sometimes result from error or forgetfulness - and that's often forgiveable. What is unacceptable, though, is doing these things and thinking it's cool (although I'm now going to admit that I have a sneaking admiration for the wearer of the odd brogues worn above with no socks).

Please take all this with a pinch of salt; but have a look at the photos and you'll see that I'm right -